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The best architecture tours of Chicago

Discover Art Deco skyscrapers, modern marvels and Frank Lloyd Wright–designed homes on these architecture tours of Chicago.

Even if you're a Chicagoan through and thorugh, there's something special about taking in the city's architecture on foot or from the water with the help of an expert. From glass and steel castles to ornate Art Deco buildings along the river to street art and cultural landmarks in various neighborhoods, there's a reason these tours are among the best attractions in Chicago . Nerd out over the design, city planning and construction behind the most beautiful buildings in Chicago on guided walks, bus rides and boat tours . First-time visitors will be happy to know that these architecture tours offer the most stunning views of the skyline —you might even be able to snap a few Instagram photos along the way. Here are a few of our favorite tours that are equally engaging for tourists and Chicago lifers alike. 

RECOMMENDED: Discover more of the best  Chicago tours

Been there, done that? Think again, my friend.

Architecture tours of Chicago

Chicago architecture center river cruise.

For a comprehensive overview of Chicago’s skyline, there’s no better vantage point than aboard Chicago's First Lady. You’ll spy more than 50 architecturally significant buildings, from the Wrigley Building to newcomers like the St. Regis. An expert guide will give you the lowdown on Chicago’s rise from the Great Fire of 1871, the advent of balloon-frame construction and other crucial moments in the city’s history. Choose to cruise by day or watch the city light up with an evening option. 

Cost: $54 for daytime cruises, $59 for evening cruises

Shoreline Sightseeing Architecture River Tour

You're certainly not short on great options to see Chicago's stunning architecture from the river. On Shoreline Sightseeing's signature 75-minute tour, you'll observe more than 40 landmarks, including Tribune Tower and Marina City. A knowledgeable guide shares the stories behind the architects, engineers, movers and shakers that gave us the nickname "City of the Big Shoulders."

Cost: $35-50

Wendella Chicago River Architecture Tour

Detailing the 130 year history of the Chicago skyline, this tour along the Chicago River is nothing short of breathtaking. Equipped with a full bar on board, a climate-controlled lounge and expert tour guides, Wendella brings luxury to the touring experience.

Cost: $44 for adults, $20 for children. 

Must-See Chicago

Want to check out Chicago's architecture but short on time? Try this 90-minute "Greatest Hits" walking tour from the Chicago Architecture Foundation, which offers an informative, fast-paced introduction to key landmarks. The tour includes stops at more than a dozen buildings, including the Chicago Theatre, Aqua Tower, Willis (Sears) Tower, the Wrigley Building and the Art Institute of Chicago. Make sure to bring something to take notes!

One of the coolest aspects of Chicago architecture is that it's always evolving, with new landmarks continuing to shape our skyline. This 90-minute walking tour from the Chicago Architecture Center is all about what's new in Chicago, taking guests to buildings like 465 North Park and the St. Regis and discussing their impact on the city's changing built environment and economy.

Frank Lloyd Wright Trust Bus Tours

These tours, led by experts dedicated to preserving and educating about the work of Chicagoland's most famous architect, are definitely not cheap, but a must for Frank Lloyd Wright superfans. (Frankenstans?) The "Wright Around Chicago" includes stops at the gorgeous Rookery Building and Wright's home and studio in Oak Park. Oh, and a prosecco toast at the Rookery Building is included.

Free Tours By Foot's Architecture Tour

If you're traveling on a budget, you can still get an excellent overview of Chicago's architecture thanks to Free Tours By Foot's pay-what-you-can two-hour walking tours. These volunteer-led tours take you to key landmarks like Cloud Gate, Marina City, the Leo Burnett Building and works by Frank Lloyd Wright, Louis Sullivan and Mies van der Rohe. 

Cost: pay-what-you-can

Art Deco Skyscrapers

Take a trip back to the Roaring Twenties with this tour, which takes you through the history of many iconic Chicago buildings. Choose from the Loop route, which includes One North LaSalle and the towering Board of Trade, or the Riverfront route for the gold-topped Carbide and Carbon building and the Holabird and Root-designed 333 N. Wacker Drive. Admire the geometric shapes, vibrant colors and sophisticated elegance that Art Deco construction is so well known for on these two-hour walking tours.

Chicago Mahogany Tours

Although these tours (which are created and by civic historian and TikTok star Shermann "Dilla" Thomas) aren't exclusively architecture-focused, the built environment plays a huge role in their explorations of the history, contributions and legacies of South Side neighborhoods like Roseland and Back of the Yards. And from Bronzeville's beautiful boulevards to Pullman's historic workers' homes, there's plenty for architecture buffs to explore on these important tours.

Chicago For Chicagoans

Live in Chicago and feel like you've done all the downtown-centric architecture tours? Maybe it's time to give Chicago for Chicagoans a go. The tours, developed for locals by locals, are designed to build community and give Chicago natives a stronger appreciation for their neighborhoods and neighbors. Enjoy walking tours and fun scavenger hunts of Albany Park, Chinatown, Pilsen, Beverly and more—and the tours frequently end at local restaurants if all that walking works up an appetite.

Cost: $10-$20 (suggested donation)

Chicago Walking Tour: Modern Architecture

If you prefer sleek metal and glass designs to ornate Gothic architecture, you’ll want to book a spot on this two-hour walking tour of the city’s most famous modern buildings. Peep minimalist designs from Ludwig Mies van der Rohe, admire the towering Aon Center and ogle the unique look of Marina City, among others.

Devil in the White City Tour

The announcement that the World’s Columbian Exhibition of 1893 would be held in Chicago spurred an explosion of new construction. Beaux-Arts buildings sprung up all over Jackson Park and the South Side—so many sparkly new buildings, in fact, that the area earned the nickname “White City.” More than 125 years later, visitors can still see the architectural impact of the fair on the city. This tour includes a visit to Jackson Park's Garden of the Phoenix and the Midway Plaissance

Private Chicago Architecture Tour

Don’t want to share your tour guide with a group? Reserve a private tour to spend an entire afternoon exploring the city’s most impressive buildings. You’ll stop at everything from Willis Tower to Gothic facades on the Magnificent Mile to Frank Lloyd Wright homes in Oak Park. Did we mention you’ll be chauffeured from stop to stop in a luxury town car or SUV, too?

Chicago Women in Architecture

As in so many industries, women’s contributions to the world of architecture have only recently begun to get their moment in the sun. Discover some of the female architects leaving their mark on Chicago’s skyline on this 90-minute tour led by an expert from the Chicago Architecture Center, featuring sites like the Aqua Tower and Equitable Building. Who built the world? Girls!

Walk Pilsen

Explore the cultural influence and impact of the many immigrant groups who have called Pilsen home and the intersection of art and architecture on this tour from the Chicago Architecture Center. On this two-hour tour, you'll visit residential, commercial, residential and cultural sites, from the 18th Street Pink Line station's murals to the Sokols, century-old Czech athletic clubs.

Brick of Chicago

What's so exciting about brick? Common brick built much of Chicago, and this tour, created by local teacher Will Quam, takes you around neighborhoods like Logan Square, Hyde Park and Bronzeville to show how the built environment created our interesting and beautiful city. After marveling at churches and greystones and Gilded Age mansions, you'll find yourself taking a second, more appreciative look at the world around you.

Historic Austin

This two-hour, neighborhood-centric Chicago Architecture Center tour takes you through historic Midway Park, shows you works by prominent local architects including Frederick Schock, William Drummond and Dwight Perkins and gives you an opportunity to marvel at the neighborhood's grand Queen Anne and Prairie homes. During the tour, you'll also hear from Austin residents about their efforts to revitalize the neighborhood following decades of disinvestment and racist housing practices.

Absolutely Chicago Segway

Of course we had to include the Segway tours! Strut around the city in style aboard these two-wheeled marvels of tour-guide technology. From museum campus to an "insider" tour that reveals the lesser-known parts of downtown, these tours are a great way to cover a lot of ground without any of exhaustion. See the lakefront, parks and skyline like never before. 

Cost: $65-$72

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CHICAGO'S ORIGINAL ARCHITECTURE TOUR®

BEST SEAT IN THE HOUSE

Choose your adventure, chicago river architecture tour (90 minutes).

Take in the world-renowned architecture as our expert guides tell the story of 130 years of architectural innovation.

We like our drinks stiff, not our tour guides.

Chicago River Architecture Tour (45 minutes)

This family-friendly introduction to the Windy City's rich history and architectural heritage features highlights from Wendella's full-length architecture tours.

The Ultimate Chicago experience.

We're In the People Business

This was one tour that I can honestly say was worth doing & probably should be a must do/ see on your visit to Chicago.

Ginette, 2023

We were recommended the architecture boat tour by a few locals and it was absolutely amazing!! Beautiful views from anywhere you sat and an extremely knowledgeable and funny tour guide led the trip. Great value for money and so so worth it. Thank you!!

Jessica W, 2024

The skyline was beautiful and the buildings all shined differently. Pictures come out amazing!

Christina, 2023

SEE FOR YOURSELF

Book your experience now.

Chicago architecture tours and cruises

From Gothic Revival survivors of the Great Chicago Fire to the birth and evolution of the modern skyscraper, the Chicago skyline is a mesmerizing homage to legendary architects and groundbreaking styles. And the best way to dive into it all is on a Chicago architecture tour.

Here’s an overview of some of the city’s amazing architecture tours, from in-depth walking tours to boat cruises along the Chicago River or Lake Michigan shoreline.

In this article

Chicago architecture boat tours, chicago architecture walking tours, chicago architecture bus tours.

Chicago Architecture Center River Cruise A top-rated architecture experience, this relaxing boat cruise aboard Chicago’s First Lady is known for its expert tour guides who share the stories behind more than 50 significant buildings.

Chicago Fireboat Tours Come aboard a real Chicago fireboat and cruise the same waterways where the historic ship once fought fires. The expert guides will highlight architecture, history, and the boat itself as you sail from Lake Michigan onto the Chicago River.

Wendella Tours and Cruises Choose your own adventure on Wendella’s architecture tours. This long-running cruise company offers lake and river excursions, with shorter and more in-depth options.

Mercury, Chicago’s Skyline Cruiseline Admire the city’s stunning skyline on this informative boat tour that covers both Lake Michigan and the Chicago River. The live narration covers the city’s rich history while pointing out architectural icons along the way.

Shoreline Sightseeing Company Discover the city and its iconic skyline from the water on these guided tours. Choose between exploring all three branches of the Chicago River or sailing down the Lake Michigan shoreline.

Tall Ship Windy You’re in for a truly unique experience aboard this 148-foot, traditional four-masted schooner, where you’ll sail Chicago’s scenic lakeshore and learn about the history of the city and its world-famous architecture.

City Cruises Admire dramatic riverfront views while enjoying an elegant meal aboard this all-glass vessel, where your brunch or lunch is accompanied by informative narration and picture-perfect views.

Inside Chicago Walking Tours Hear about the hidden details and real stories of Chicago’s legendary architecture on an Inside Chicago Walking Tour. These in-depth tours take you inside some of the city’s most fascinating buildings, from Art Deco masterpieces to famous movie locations.

Free Tours by Foot The name says it all. These budget-friendly excursions use a “pay-what-you-can” model. Their architecture-themed tour takes you along the Chicago Riverwalk and throughout the Loop and Millennium Park.

Tours With Mike Led by an award-winning guide, Tours With Mike offers a unique perspective on the city’s architecture. One popular route is the Ugly Buildings tour, an “educational roast” of some of Chicago’s lesser-known spots.

Chicago Greeter For the architecture junkie who’s also on a budget, the free Chicago Greeter program pairs you with a local who’ll highlight either downtown or in your pick of the city’s neighborhoods. If you don’t get a chance to register in advance, look into an on-the-spot InstaGreeter  walk instead.

MetroWalkz Self-Guided Walking Tours Explore Chicago at your own pace with a free, self-guided walking tour. Just select one of MetroWalkz’s digital, mobile-friendly tours, showcasing several unique areas of the city. Their Loop Architecture Tour will give you a good overview of Chicago’s downtown.

Big Bus Chicago : These hop-on, hop-off bus tours are a great way to explore Chicago’s architecture at your own pace. The route cruises by all the city’s top landmarks. Hop on to hear pre-recorded commentary, hop off to get out and explore on your own.

Chicago Mahogany Tours : Immerse yourself in Chicago’s neighborhoods, from Bronzeville to Pullman, on these bus tours that touch on everything from architecture to culture, with an emphasis on Black history.

Chicago Architecture Center : These in-depth bus tours, led by seasoned guides, cover a wider variety of topics, like historic houses of worship, the Chicago World’s Fair, Gothic-style architecture, and beyond.

From this article

Tours & Attractions

Rookery building.

Absolutely Chicago Segway Tours

Skydeck Chicago

Inside Chicago Walking Tours

eVisitorGuide and MetroWalkz Tours

The Magnificent Mile

Special Event Venues

360 chicago observation deck.

Wendella Tours & Cruises

Mercury, Chicago’s Skyline Cruiseline

Shoreline Sightseeing Company

Streeterville

Chicago’s First Lady Cruises

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Travels & Treasures

9 Great Chicago Architecture Tours

This post may have affiliate links which is used to cover administrative costs at no additional charge to you. I pour my heart into providing quality insights, and your support means the world to me. (Full Disclosure)

If you’re looking for the best Chicago architecture tours, you’ve found them here! As a local who has explored these tours on weekends, during staycations, or while showing visiting friends around Chicago, I can honestly say that this list shares the most unique and fun experiences.

The city has great options including the best architectural boat tours, helicopter tours, walking tours, and more.

If you have limited hours, take the Hop On/Hop Off bus tour in Chicago or visit the top Chicago attractions to get the most out of a short amount of time. Real all about this in this roundup post!

Table of Contents

Best Chicago Architecture Tours

Chicago architecture cruise.

If you love touring on water, then this cruise is for you. I’ve taken this cruise several times while showing friends the city and they loved it too.

On this cruise, you will ride the Chicago River and see the city’s famous architecture. You’ll see the impressive flat skyline including over 40 famous buildings such as Navy Pier, the Wrigley Building, and the John Hancock Building with audio narratives. The tour covers all three branches of the Chicago River.

Navy Pier Centennial Wheel Regular & Express

This is one of my favorite ways to see the city and the Chicago skyline. You circle only once, but the ride is super slow, and you’ll have some great photo ops when you get to the top.

Navy Pier is among the most visited destinations in the world. It offers beautiful views from the wheel, and it’s a must-do when in the area! Located right on the pier, you have spectacular views of the city’s skyline, architecture, and waterfront.

45-Minute Private Helicopter Flight

I was scheduled to go on this flight but it was canceled due to bad weather. At least they are good at following safety protocol. Too bad that I missed this amazing experience by helicopter. From what I hear, you will get the best views of touring Chicago architecture, and the experience of flying amongst the clouds. 

Willis Tower Skydeck and The Ledge

Having been on the Skydeck a couple of times, it never disappoints. What I didn’t like much was that there is a limited time that you have to stand in the box. But if there were no supervision, the line would be from the street.

But here, you will have some of the most breathtaking views of Lake Michigan. You’ll also see why home is to beautiful parks and cultural attractions such as the Adler Planetarium, Millenium Park, the Shedd Aquarium , and Grant Park.

Look north to see Chicago’s iconic skyscrapers and landmarks from Lincoln Park to the world-famous Wrigley Field.

Night Tour with Willis Tower Entry & Skyline Cruise

This tour is a wonderful way to spend the evening while touring in Chicago. You’ll immerse yourself in one of the tallest architectural buildings in Chicago along with a Chicago boat tour. 

Experience the Windy City’s most popular attractions on this overnight tour. Watch the night light show of Buckingham Fountain. Cruise along the Chicago skyline and climb to the top of the iconic Willis Tower.

Big Bus Panoramic Sunset Tour with Live Guide

If this is your first visit to this city, this is a great way to tour Chicago , Illinois and how it shines at night. There is so much to see on both sides of the bus since the architecture of Chicago is interesting.

Experience the stunning skyscrapers of Windy City that light up at night. Take a panoramic nighttime tour from the Magnificent Mile to Michigan Avenue past the Chicago Theater and Buckingham Fountain.

Chicago History, Culture, and Architecture Walking Tour

This is a great way to hear about Chicago’s history and architecture. Take a private stroll or share walks with family or friends for this architecture tour. You can see old and new architecture, try delicious local treats, see beautiful boats tour the river. 

I also recommend visiting the Jane Addams-Hull Ho use Museum for a firsthand experience of the artifacts and memorabilia that tell the story of this pivotal institution for social reform.

Chicago Architecture Center Exhibit Admission

The Chicago Architecture Center or CAC is located at the south end of Magnificent Rock near Michigan Walker Intersection. You’ll discover super-sized models of architecture from around the world.

The vouchers give you access to two floors of imaginative exhibitions at the city’s newest cultural venue.

Chicago Art Deco Skyscrapers Walking Tour

The luxurious materials and geometric decorations of Art Deco represent the opulence and optimism of the decadent 20s. Visit some of the city’s most beautiful architecture and learn about the history and characteristics of this modern decorative style.

Final Thoughts on the Best Chicago Architecture Tours

These are the best ways to tour Chicago architecture and see all the unmissable attractions. I’ve taken almost every single one of these tours, including ones not mentioned and found them worth the money.

I enjoyed seeing the towering skyscrapers and iconic landmarks. The tours offer a fascinating glimpse into the architectural history of the Chicago. Not to mention, it’s nice to play tourist in my own back yard.

As a visitor, be sure to plan your tour in advance and consider factors such as weather and time of day to make the most of your experience. Don’t forget your camera to capture the stunning views along the way.

Whether you’re an architecture enthusiast or simply looking to appreciate the city’s remarkable skyline, a Chicago architecture tour is a must-do activity. The buildings are inspiring structures, and some are a marvel of innovative designs that have shaped this iconic city.

Whether you go on water, in the air, or on foot , book your tour today and embark on a journey through Chicago’s architectural wonders.

Tanya, a travel writer and content creator who has lived in Chicago for over 30 years, is your go-to local expert for Chicago's hidden treasures. Tanya's deep knowledge of various cities and attractions is acquired through personal exploration, making her articles a treasure trove for travelers and families. She has visited 43 of the 50 United States, France, Italy, Spain, Portugal, Japan, and the UK.

Chicago architecture tours – tickets, cost, hours, duration, departure address

The skyscrapers and buildings of Chicago have helped shape American architecture.

Legendary architects from different periods have contributed to building the iconic skyline of the Windy City.

There are many ways to explore and learn about the architecture of Chicago.

This article covers everything you must know about buying tickets for the Chicago Architecture Tours.

Top Chicago Architecture Tours

# Chicago River Architecture tour # Chicago Architecture tour on Michigan Lake # Chicago Architecture Center’s walking tour

Table of contents

What to expect.

Take a dive deep into the modern architectural and cultural marvel that is the city of Chicago by opting for a Hop-On-Hop-Off bus tour, a Chicago River Cruise, a Speedboat cruise, or a Walking tour.

Sail down all three branches of Chicago on a cruise equipped with a bar and see the legendary landmarks of Chicago such as the Wills Tower, John Hancock Building, Tribune Tower, Buckingham Fountain, and more.

Step on the outer deck and feel the cool river breeze while you explore the beautiful city without the hassle of traffic or congestion.

Opt for a speedboat ride and see the city views with a thrilling ride that tears through the water, throwing water sprays all around.

Take the walking Art Deco tour and be led up close to mesmerizing Chicago buildings and their architecture, reading their motifs arising from a union of Cubism and the ancient architecture of the Middle East.

Visit Chicago’s most beautiful attractions, such as Millennium Park, and enjoy classic Chicago specialties like deep-dish pizza, hot dogs, and Italian beef sandwiches.

Be led by an expert guide on all tours who will entertain you with stories and insights about Chicago and the attractions you come across.

Use the evergreen Hop-on-Hop-off bus tour of Chicago to explore the best of Chicago from the unique vantage point of a big bus, getting on and off at the many convenient stops throughout the city.

Where to book tickets

Tickets for the Chicago Architectural Tour  are available online and at the attraction.

Online ticket prices tend to be cheaper than tickets at the attraction.

When you buy online, you can avoid the long queues at the ticket counters. 

Because Chicago Architectural Cruises sells limited tickets, they may sell out during peak days.

Booking early helps avoid last-minute disappointments.

How do online tickets work

Visit the ticket booking page for Chicago River Architecture Cruise: Skip-the-Ticket-Office , select the preferred date, time slot, and number of tickets, and buy the tickets immediately.

Once you purchase tickets, they get delivered to your email address.

There is no need to get printouts of the ticket. 

Show the e-ticket on your smartphone at the entrance and walk in. Please carry a valid ID with you.

Chicago Architectural Cruises ticket prices

For Chicago River Architecture Cruise: Skip-the-Ticket-Office , the general ticket for all ages above 13 costs US$51

Kids between three and 12 can gain access at US$29

Infants under three are not charged anything.

For Chicago: 45-Minute Family-Friendly Architecture River Cruise , the general ticket for all ages above 13 costs US$28

Kids between four and 12 can gain access at US$13

Infants under four are not charged anything.

For Chicago: 75-Minute Architecture Cruise by Speedboat , the general ticket for all ages above 13 costs US$60

Kids between 3 and 12 can gain access at US$48

For Chicago: Art Deco Skyscrapers Walking Tour , a ticket for all ages costs US$30.

For Chicago: Favorite Foods Guided Walking Tour , the general ticket for all ages above 13 costs US$80

Kids between four and 12 can gain access to US$70

Infants under four are not charged US$10 for participation.

For Chicago: Hop-on Hop-off Sightseeing Tour by Open-top Bus , the general ticket for all ages above 13 costs US$49

Kids between three and 12 can gain access at US$36

Chicago architecture tickets

Depending on your tastes and preferences, you have the option of booking a Chicago architecture tour on a boat, bus, speedboat, Segway, etc.

Or if you love walking, you can explore the city on foot as well.

We explain all the different types of Chicago Architecture tours available –

Architecture tours by boat

Tourists can choose from two types of Chicago Architecture boat tours.

You can book a scenic boat trip along the Chicago River or book a Lake Michigan tour.

Chicago River Architecture tour

This is a 75-minute boat tour best for those who want to understand the city’s architecture.

You will cruise along the Chicago River to discover architectural gems among the city’s renowned landmarks.

A local guide shares stories and anecdotes, keeping the atmosphere lively.

The boat passes more than forty buildings and sails under historic bridges.

The tour is available in English and Spanish.

Ticket Prices

Adults ticket (13+ years): US$51 Child ticket (3 to 12 years): US$29

Infants under three are not charged any fee.

Chicago Architecture tour on Michigan Lake

If you want more of a joy ride with a little bit of Chicago’s architecture thrown in, you must book this tour.

During this 40-minute classic tour of Michigan Lake, you get to see Chicago’s shoreline and its iconic landmarks.

Adults ticket (13+ years): US$13 Child ticket (4 to 12 years): US$28

Infants under four are not charged any fee.

Walking tours

Many tourists prefer a Chicago Architecture walking tour to understand the architectural marvel of Chicago.

We have identified two of the best walking tours in Chicago.

Chicago Architecture Center’s walking tour

During this 90-minute tour, you will explore the lobbies of five opulent Art Deco skyscrapers on the banks of the Chicago River.

Chicago Architecture Center, the city’s best authority on architecture, trains these guides.

This tour is wheelchair friendly.

This ticket also gets you access to the Chicago Architecture Center exhibits .

Ticket Price (All ages): US$30

Chicago Favorite Foods Guided Walking Tour

This comprehensive three-hour tour allows you to see some of the most iconic sites, such as the Millennium Park, Magnificent Mile, Wrigley Building, and more.

You will get to sample some of Chicago’s most famous dishes, including the deep dish pizza, the beef sandwich, and the Chicago Hotdog, and can also opt for a craft beer.

You will be led by an expert guide.

Adult ticket (12+ years): US$80 Child ticket (4 to 11 years): US$70 Infant ticket (up to three years): US$10

Speedboat architecture tour

If you want to cruise on both the Chicago River and Lake Michigan and explore the architectural marvel of Chicago, look no further than the Chicago Architecture tour by speedboat.

Besides the buildings, you will also pass through the historic Chicago Locks and sail under numerous bridges on the Chicago River during this tour.

Seadog Speedboat is an open-air vehicle.

Adults ticket (13+ years): US$60 Child ticket (3 to 12 years): US$48

Chicago Architecture Center’s bus tour

Chicago Architecture Center, the city’s leading authority on architecture, offers the Chicago Architecture tour by bus.

During this three-and-a-half-hour tour, you will cover approximately 48 km (30 miles) of the city.

Being an extraordinary architecture tour, it is available only on Saturdays.

This tour also includes access to the Chicago Architecture Center.

Adults ticket (13+ years): US$49 Child ticket (3 to 11 years): US$36

Back to Top

Best Chicago architecture tour companies

Some tourists prefer to know about the architectural tour operator before booking their trip.

They have heard or read positive reviews about a tour operator and want to book their tour.

This section details the top five Chicago Architecture boat tour providers –  Shoreline Sightseeing ,  Chicago Line Cruises ,  Wendella Sightseeing ,  Chicago Architecture Foundation , and  Seadog Cruises .

Shoreline Sightseeing

Shoreline Sightseeing has the city’s largest fleet – 11 boats and six water taxis, and dozens of architectural guides, making it one of the most popular tour operators.

According to TripAdvisor, Shoreline Sightseeing’s architectural boat tours are usually the most booked in the whole of America.

With their state-of-the-art tour boats and well-trained guides, Shoreline Sightseeing presents the story of Chicago’s architecture in the best possible way.

If you are traveling with your family or want a laid-back excursion, look no further than Shoreline.

Shoreline Sightseeing’s tour timings

Shoreline Sightseeing’s tours  start from Navy Pier and Michigan Avenue, and both have the same timings.

The first tour sets sail by 10 am, and the last tour sets off at 5.45 pm.

There are eight other timings you can choose from – each 90 minutes apart in between these two slots.

If you want a tour with a Spanish guide, you have only one option – the 9.30 am tour starting from Michigan Avenue.

Shoreline Sightseeing departures

Shoreline Sightseeing’s boats depart from two places – the Navy Pier and Michigan Avenue.

While booking your ticket, you can decide where you want to start their architecture tour.

Navy Pier: Shoreline’s boat boarding line is at Navy Pier’s Polk Bros Park. Their Navy Pier’s address is 600 East Grand Avenue, Chicago, IL 60611.

Watch out for greeters in bright orange.

Michigan Avenue : This boarding line is by the Chicago River at 401 N. Michigan Ave. Chicago IL 60611. Head towards the East of du Sable Bridge (Michigan Ave. Bridge) and on the North Shore of the Chicago River.

Look out for tour operator’s folks in bright orange.

Review of Shoreline Sightseeing

Shoreline Sightseeing has a high rating of almost 5 out of 5 stars on TripAdvisor and 4.8 out of 5 on GetYourGuide.

Even though Shoreline Sightseeing offers a family-friendly atmosphere, a good chunk of reviews come from couples suggesting that the tour works out best for families and couples.

Most of the reviewers felt the tour offered was either ‘Excellent’ or ‘Very Good.’

Many of the reviews contained the terms ‘great tour’ and ‘highly recommend this tour’ to describe their experience.

Note: If you want to save money on Shoreline Sightseeing’s architectural tour of Chicago and other City attractions, check out Chicago Go Card

Wendella Sightseeing

Wendella Sightseeing was the pioneer of Chicago’s architectural tours.

Wendella Sightseeing offers two flavors of architecture tours – the river-only tour and the river & lake tour.

This operator takes you through the heart of the city on all three branches of the Chicago River, even as the expert local guide enthralls you with stories on 130 years of design innovation.

Their ships are all climate-controlled boats, and you won’t have to worry about rain or wind.

The best part is the full-service bar, which serves snacks and a selection of beers, wines, cocktails, and soft drinks.

Wendella boat tour timings

Wendella Sightseeing’s river tours  start as early as 10 am and go on till 9 pm during peak seasons.

The most popular Wendella boat tour is the one at 12.15 pm. Because both indoor and outdoor seating is available, tourists don’t mind the overhead sun.

The other favorite time slots are 3 pm, 4 pm, and 5.45 pm.

If you want to book a Wendella Sightseeing boat tour on both the Chicago River and Lake Michigan, your options are 10.15 am (most popular), 1 pm, 2 pm, and 4.45 pm.  Book Chicago River & Michigan Lake tour

Wendella Sightseeing’s departures

Wendella Sightseeing boats set sail from their Michigan Avenue Docks located in the heart of Chicago’s Magnificent Mile.

They have two docks (look at your voucher to know where your boat will take off from).

Main Dock : The Main Dock is located at 400 North Michigan Avenue at the NorthWest corner of the Michigan Avenue Bridge, which is now called the DuSable Bridge.

This dock is on the Chicago River, at the base of the Wrigley Building, made of white marble. It is also known as the East Dock. Directions

Trump Dock : Trump Dock is at 401 N Wabash Avenue, on the west side of the Wrigley building on the Chicago River. It is also known as the West Dock. Directions

Review of Wendella Sightseeing

On Tripadvisor , Wendella Sightseeing has a high rating of 4.5 out of 5.

Even though the tour operator doesn’t differentiate, more couples seem to be booking this tour, followed by families and groups of friends.

Many of the reviewers used the terms ‘great tour,’ ‘great boat,’ and ‘guide was very knowledgeable’ to describe their experience.

The guides also came in for praise for the interesting facts they shared about the Chicago buildings.

Chicago Architecture Center

Chicago Architecture Center (CAC) was earlier known as the Chicago Architecture Foundation (CAF).

This is why the architecture tours offered by Chicago Architecture Center are also often referred to as ‘CAF tours.’

The CAC provides beautiful Art Deco walking tours of Chicago.

Chicago Architecture Center’s tour timings

The CAC Art Deco tours start at 10 am or 2 pm, depending on the day selected.

The tour lasts for 90 minutes

CAC tour departures

Chicago Architecture Center’s tours instruct you to arrive 10 minutes before departure at 30 N LaSalle Street and have your confirmation at hand.

The docent will check your name off a list of attendees. Get Directions

Watch out for the blue awning marking the stairway entrance.

Seadog Cruises

Since Seadog Cruises specializes in thrill rides, their architectural tours in Chicago come with a twist – they happen on speedboats.

The speedboats make it an exciting learning experience for all age groups.

However, if you are elderly with back or neck problems or pregnant, this tour isn’t for you.

Seadog architectural tour timings

The  Seadog Speedboat architectural tour  has morning and afternoon options.

If you prefer a pre-lunch tour, you can book the 11.15 am or the 1.15 pm architectural tours.

If you prefer afternoons or evenings, there are three times you can opt for: 3.15 pm, 5.15 pm, or 7.15 pm.

Seadog speedboat departures

SeaDog boat tours sail from Navy Pier’s Dock Street, located at 600 E. Grand Avenue, Chicago IL, 60611.

You can’t miss Seadog’s speedboats just below the Ferris Wheel and across from the Grand Staircase. Get Directions

Review of Seadog Cruises

Seadog Cruises is rated 4.5 out of 5 on Tripadvisor .

Families, couples, and groups of friends reviewed the Seadog River and Lake architectural tours highly.

Many of the reviewers used the terms ‘extreme thrill ride,’ ‘a lot of fun,’ and ‘super fun’ to describe their experience.

If you would prefer a quiet and informative architectural tour, this isn’t for you.

How long do the Chicago architecture tours last

Most popular Chicago architecture boat tours last around 60-90 minutes, and walking architectural tours usually last around two hours.

The duration of Chicago architecture tours depends on many factors, such as – the mode of transport (regular boat, speedboat, walking, etc.), the route to be followed, the number of buildings in the itinerary, stoppages, is it the river cruise or lake cruise or both, etc.

The minimum duration of any architectural trip is usually one hour.

Boat tours during rain

Usually, tours depart rain or shine.

Some boats are covered, and some aren’t.

You may have to brave it and continue with the tour if it’s a drizzle.

However, the captain’s word is final in severe weather.

If he/she says that it is unsafe to continue and cancels the tour, all guests are refunded.

TripAdvisor is full of reviews of tourists who enjoyed their architectural boat ride (or walking tour) even though it was raining.

Boat tours in winter

Even though winter is a great time to travel in Chicago (no crowd, lower prices, etc.), it is not the best time for architecture boat tours of Chicago.

The river freezes over every winter with a sheet of ice on it, making it dangerous for the boats to venture out.

This is why most tour boats get parked in the dry docks by Thanksgiving.

A few boats are listed as all-season tours, but we don’t recommend that because the weather won’t be conducive to being on the water.

If you are in Chicago during winter, the best option is the Chicago Food walking tour .

Our second best will be the three-and-a-half-hour Chicago architectural highlights by bus .

Chicago Explorer Pass architecture tour

Did you know that with the Chicago Explorer Pass, you can book a Chicago architecture tour for free?

Chicago Explorer Pass is a discount card that can get you around 40% discount on top Chicago attractions, including Shoreline Architecture River Cruise, 360 CHICAGO, Skydeck Chicago, Hop-On-Hop-Off Bus, and 20 other attractions.

Since the card is valid for 30 days, you can pace your sightseeing.

You can skip the ticketing lines in all the attractions and thus save yourself a lot of time.

Popular attractions in Chicago

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This article was researched & written by

Jamshed V Rajan

He is a two-faced traveler, who enjoys both the hustle-bustle of an urban holiday and the serenity of a break from the rest of the World. During some of his vacations, he is a resort hopper, and on others, he barely spends time in his hotel. He loves to try mouth-watering local cuisines, especially non-vegetarian dishes. Favourite Cities: Amsterdam, Las Vegas, Dublin, Prague, Vienna

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Chicago Architecture Tours

Chicago is renowned for its architecture. In the nineteenth and twentieth centuries, some of the most innovative architects lived and worked in this city, creating iconic buildings that stand today as legacies of their signature style. Several of the most striking buildings in the country can be found in Chicago, from the distinctive Prairie style of Frank Lloyd Wright to the chic modernism of Ludwig Mies van der Rohe. For those interested in exploring this fabulous collection of worldly architecture, an architecture tour is a smart choice. Fortunately, Chicago abounds with options including everything from river cruises to walking tours.

One of the best ways to see the city’s architecture is actually from the water! Companies like Shoreline Sightseeing offer river cruises that showcase top architectural landmarks like the Tribune Tower, the Wrigley Building, Marina City, and more than 40 examples of unique Chicago architecture. These cruises provide plenty of photo opportunities, and are a relaxing way to enjoy a fully-narrated journey through the city’s architectural heritage.

Another, more widely available option for exploring Chicago’s remarkable architecture is the walking tour. Multiple companies offer walking tour options, ranging in length from two to four hours. You can choose walking tours that cover indoor or outdoor attractions (indoor options are more common in the wintertime months, to help you avoid the often bitterly cold Chicago winter). Some top sites on one popular winter tour from Chicago’s Finest Tours, for example, include Millennium Station, Chicago Cultural Center, Daley Center, City Hall, and the State Street Macy’s.

A few tours even combine an architectural focus with other components like food and drink. Chicago Detours, for one, offers a tour of architecturally significant bars. There are also several architecture tours that focus on important moments in Chicago history, like the 1893 World’s Fair & Columbian Exposition. Others focus on contemporary architecture and more modern construction, so there’s a tour focus to suit practically every interest.

Then, of course, there’s the Chicago Architecture Center, which offers over 80 different tour options, which include walking tours, bus tours, bike tours, L train tours, and cruises. They feature cruises sorted by venue, neighborhood, style, genre, and more. Popular tours include a cruise aboard the vessel called Chicago’s First Lady, a tour featuring architectural highlights of the entire city on a 3.5-hour bus ride, a walking tour that showcases the golden age of Chicago architecture found along Michigan Avenue and State Street, and a two-hour excursion that points out Chicago architecture from the distinctive vantage point of L train stops and stations.

Architecture tours come in many styles, but here’s a few of the most popular tours and tour companies:

Chicago Theatre Tour

Chicago is home to one of the best theater scenes in the country. Among the shining jewels of this community is the historic Chicago Theatre. Take a tour of this magnificent venue, built in 1921 and home to generations of top theatrical talent in the decades since. Go behind the scenes to see the gorgeous French baroque interiors and celebrity autographs on the walls.

Chicago Architecture Center

This non-profit organization runs an extensive variety of acclaimed tours highlighting Chicago’s many remarkable buildings. Favorite tours include the Chicago River Cruise tour, the Art Deco Skyscrapers tour, and the Chicago Architectural Highlights tour.

Shoreline Sightseeing

Has been running scenic tours of Chicago along Lake Michigan and the Chicago River for 80 years. Their most popular tours include a river excursion highlighting Chicago’s acclaimed architecture and a lake cruise departing from Navy Pier.

7 of the Best Architecture Chicago Tours

Are you looking for the best architecture Chicago tours? These are some of the most recommended ways to explore and interact with famous Chicago architecture.

Planning a trip to Chicago is super exciting! If you’re anything like me, you’re here because you love to research and plan your trip ahead of time. As a midwest girlie, I am giving you ideas for the best ways to experience architecture in Chicago.

You are going to learn about tours to experience by boat, walking, and opportunities to learn about famous architects. After learning about these tours, you are going to be ready for your next Chicago travel adventure!

This post is my 7 of the Best Architecture Chicago Tours.

Architecture chicago tours.

Surprisingly, Chicago has so many different types of architecture styles. From art deco, prairie school, contemporary, to mid-century modern, there is a style for everyone. One of my favorite things to do when I travel to a new city is to do an architecture tour. I always learn so much about the city’s history, style, and a lot of fun facts. In Chicago, there are so many exciting ways to experience architecture. Check out below 7 of the Best Architecture Chicago Tours.

1. Boat Tour

One of the most popular ways to experience Chicago architecture is on a boat! Along the Chicago River, there are several famous buildings built in different time periods that can be appreciated. It’s also a unique experience to see these buildings from a lower vantage point. There is something special about sitting on a boat and looking up at these marvelous works of art.

I highly recommend Wendella tours and cruises. They have been in operation for over 80 years! They offer several different types of cruises, and either a 45 minute or 90 minute architecture tour. Definitely go for the 90 minute tour because you’ll need those extra 30 minutes to really appreciate the engineering. Many of my friends have lived in Chicago, and this is the company that they always recommend to their friends and family when they visit.

The Chicago Architecture Center recommends taking a tour with the company Chicago’s First Lady . On our most recent visit to Chicago, we chose to do this tour. It was a lot of fun (despite the rain)! They offer a variety of tours as well, and we chose to do the hour and a half long option. When weather is unpredictable, I like having the option to sit on the open deck or below where it’s covered from the elements. 

On these Chicago River tours, you’ll have a chance to see famous buildings like the Willis Tower, Navy Pier, the Wrigley Building, Tribune Tower, Merchandise Mart, Lyric Opera, 333 West Wacker, and Marina City. 

2. Kayak Tour

Another option on the Chicago River is to do a kayak tour! If you’re looking for a more intimate experience, check out Wateriders . They offer a variety of themed tours, but I would definitely do their history and architecture tour. You’ll be able to see the iron work of the river’s bridges up close and personal from the seat of your personal kayak. I like how this tour combines historical fun facts while also learning about the architectural styles of landmark buildings. 

For those who may not be experienced kayakers, Kayak Chicago provides a review of paddle strokes, safety, and rules of the water before every tour. Their tour is 3 hours long and will showcase a variety of Chicago’s best architecture styles and stories of its past. 

3. Walking Tour 

Moving on from the Chicago River, the next best way to experience architecture in Chicago is on a walking tour! The Chicago Architecture Center offers a variety of walking tours. 

For an introduction into history and architecture, I recommend doing their A Walk Through Time tour. It’s a 90 minute, guided tour that goes in chronological order, experiencing early skyscrapers to high rise buildings.

If you’re more interested in Art Deco like I am, consider doing the Art Deco Skyscrapers: The Riverfront tour . This tour explores many of Chicago’s beautiful Art Deco buildings. Not only will you see the exterior of these buildings, but also experience their stunning lobbies. Discover buildings like the Carbide and Carbon Building (now Pendry Chicago), the Chicago Motor Club Building (now the Hampton Inn) and the wonderful Trustees System Service Building (now the Century Tower).

Other than Chicago Architecture Foundation, Free Tours by Foot offers a 2 hour architecture walking tour. This tour starts in daylight and ends after dark. I love the idea of exploring the city’s landscape in both light and dark settings. In the daylight, you’ll be able to appreciate the details of buildings’ facades and at night see how the city sparkles. 

The fun thing about Free Tours by Foot is that all of their tours are on a “name-your-price” cost, making it budget friendly. Check out their website to find more walking tours and other cities to explore. 

4. Bus Tour 

Next up on my list of best architecture Chicago tours, is to tour by bus. Another Chicago Architecture Center tour is the Architectural Highlights by Bus . This bus tour is 3 and a half hours long and explores a variety of Chicago neighborhoods such as Hyde Park, Kenwood, Bronzeville, the Loop, the Gold Coast and the Magnificent Mile. You’ll see architectural masterpieces at stops in the Loop, Hyde Park, Illinois Institute of Technology and the Museum Campus. The cool part about this tour is that some interiors are included, like the Frank Lloyd Wright restored Robie House, now a UNESCO World Heritage Site (which you’ll learn more about in this post). 

If you’re looking for a more casual option, consider Big Bus Tours Chicago . They offer a hop on hop off tour which is great if you are short on time or are looking to explore a specific area. The tour includes 13 different stops throughout Chicago. This is a great way to explore the city’s architecture while also having a chance to spread it out over the course of a day or weekend.

5. Segway Tour 

A very unique way to explore Chicago’s architecture is by doing a Segway tour. If you’ve never done a Segway tour and want to learn more about my own first experience, check out my post 3 Extraordinary Days to Travel North Carolina .

In Chicago, Absolutely Chicago Segway Tours offers an Art and Architecture tour! This tour starts in the Southeast corner of Millenium Park. Not only will you see artwork, architecture, and famous landmarks, but you’ll also see the beauty of the lakeshore and gorgeous public parks. I highly recommend doing a Segway tour. It’s a really cool way to explore a new city, is faster than walking, but still allows for a close up experience. 

6. Self-Guided Tour 

Sometimes we’re in the mood to just walk around a city at our own pace and without the help from a tour guide. When I’m feeling that way, I enjoy taking a self-guided tour. I love that self-guided tours allow the freedom to explore what I want, when I want, and I can adjust it to what I want to see most. 

I love using GPS My City guides for self-guided tours. They offer several guides in several cities. For Chicago architecture I would recommend the Loop District Architecture Walking Tour . 

Another great option is the EVisitor Guide’s Grant Park/Art Institute Tour . Grant Park is one of the spaces which Daniel Burnham, famed architect and city planner, envisioned for Chicago back in 1909. Today it is the site of many of Chicago’s summer festivals, including Blues Fest, Taste of Chicago, and Lollapalooza. What I like about these self-guided tours is that they include audio! It eliminates the tedious job of reading while walking, making it a more relaxing experience.

7. Frank Lloyd Wright Tour

Last but not least, I highly recommend doing a Frank Lloyd Wright tour. A superstar American architect, Wright is the pioneer of the prairie school movement. Many of the houses, offices, skyscrapers, churches, and schools he designed during his 70 year creative period can be found in the midwest. Chicago offers a variety of Frank Lloyd Wright’s pieces and can be found in the form of houses, churches, and offices. Below are two of my most recommended tours.

Chicago Architect Center offers an hour-long Frank Lloyd Wright in Oak Park tour. The tour covers almost a dozen homes! Because the tour is so robust, it only allows for viewing of the exteriors of the homes. 

For a more intimate experience, Wright Around Chicago is a small-scale bus tour hosted by the Frank Lloyd Wright Foundation that goes throughout Chicago to see many well known sites and homes. Included in the tour are two UNESCO recognized works, the Unity Temple and Robie House. 

If you are super passionate about architecture and have enough time to do several tours, consider becoming a member of Chicago Architecture Center. Once a member, all of their tours are included! This is a great way to save some money while also supporting an amazing organization. 

Recommended post for more architecture: 4 Days in Savannah Georgia | What to do in Savannah Georgia .

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The Kinzie Street Bridge, through which a tour bus belonging to the Dave Matthews Band dumped hundreds of pounds of wastewater onto a passenger sightseeing boat in 2004.

Tyler Pasciak LaRiviere/Sun-Times

20 years after that disgusting Dave Matthews Band incident, victims now can laugh about it

‘it was just terribly upsetting,’ says captain of the boat doused with liquid waste from the rock group’s tour bus that fateful day..

Tracy Dangott expects a deluge of snarky texts from friends on Thursday.

The day — Aug. 8, to be exact — will mark the 20th anniversary of what’s popularly known as The Dave Matthews Band Incident.

On that sunny Sunday afternoon in 2004, a bus driver for the rock group passed over the Chicago River and discharged 800 pounds of liquid waste from the vehicle’s septic tank that passed through the steel grating of the Kinzie Street Bridge and showered dozens of passengers who were enjoying an architectural boat cruise.

Dangott and his then-wife and two friends were on the part of the boat that got it the worst.

He was 29, wearing a Hawaiian shirt and had a motorcycle helmet in his lap that acted like a soup bowl.

“It’s one of those things that’s had more importance in the cultural zeitgeist than it possibly should. What the hell? Why are we talking about this 20 years later?”

Dangott, who works in the financial industry, raised his voice to ask a few of his younger colleagues whose desks are outside his office: “Have you heard of The Dave Matthews Band Incident?”

A few seconds go by.

“Yeah, they’ve heard of it ... and now they’re reenacting it,” he said. The bit of theater consisted of hands in air, stunned looks on faces.

The following exchange went like this: “You saw it happen?” “I was on the boat.” “Did you get hit?” “Very much so.”

Dangott said he washed his motorcycle helmet out with a hose when the boat got back to the dock near Michigan Avenue. He then put it on his head and zoomed back to his Lake View home on his Kawasaki. His spouse, who also got doused, clung to his waist. He called his doctor, who suggested they get hepatitis shots the next day.

Chicago’s Little Lady tour boat passes under a downtown bridge recently with a few passengers on its top deck. It was packed the day it was splashed by the contents of the septic tank of a Dave Matthews Band tour bus on Aug. 8, 2004.

Mitch Dudek/Sun-Times

“It was the worst experience,” he said with a laugh.

Dangott said he still has the T-shirt his boss bought for him shortly after the incident. A Dave Matthews Band tour bus on the front, dates and cities of each show from that tour on the back.

The episode is really funny . . . in hindsight.

“It took me a good solid year before I could laugh at it. I was just angry and disgusted for the first six months,” said Dangott, who expects a flood of the usual texts from friends on the anniversary of the incident. They usually consist of a picture of a plaque someone placed on the bridge commemorating the incident.

Nancy Todor, who was sitting next to Dangott, also expects a flood of text messages this week reading “Happy poopiversary!”

She’s been laughing at the moment since it happened.

“I have a twisted sense of humor, so at the same time that I was crying and throwing up, I was laughing, too, because you can’t make this s--- up, pardon the pun,” she said.

“All I remember is looking and seeing a bus and then a rust-colored waterfall,” said Todor, who worked in the financial industry back then but has since become a grade school teacher in the western suburbs. “I have a very strong gag reflex. I avoid outhouses like the plague.”

Thankfully, a pal who also got splashed had a convertible and gave her a lift to her home in Elmhurst with the top down. She took a two-hour shower, called lots of friends and family to tell them what happened, then went to dinner at Mon Ami Gabi in Oak Brook and told the wait staff, too.

“I just had to get it out of me; I told everyone,” she said.

She cut her long wavy hair short the next day.

It took years before Sonja Lund, who was 24 and the captain aboard Chicago’s Little Lady that day, could laugh about it.

Images that come to her mind from that day are a baby who wouldn’t stop crying and an old lady with hair matted to her head.

“When it became clear what I needed to do, I hammered down on the throttle and we just blasted back to the dock,” said Lund, noting that she broke the no-wake rule on the river and may have bounced some smaller boats around a bit and tipped a kayaker or two.

“I told the bartender to open the bar and give people anything they wanted — a shot of whiskey, bottle of water — just give it to them, anything to make them more comfortable and calm people down,” she recalled, emphasizing her concern at the time that people might jump from the boat in disgust. (No one did.)

“It was a few years before I could take it a little less seriously. It was just terribly upsetting, and I was like ‘Why is everyone laughing? It’s not funny. It’s terrible.’ ”

Her evolution is clear as she says the last two sentences with a tinge of laughter.

She hopes everyone on the boat has skewed toward humor over time.

Stefan Wohl, the bus driver for the Dave Matthews Band, arrives to turn himself in to police in 2005.

Sun-Times file

Bus driver Stefan Wohl, who was alone as he was headed east to the Peninsula Hotel, was charged with misdemeanor counts of reckless conduct and discharging contaminants to cause water pollution. He pleaded guilty, was ordered to pay the Friends of the Chicago River $10,000 and perform 150 hours community service in the community in Texas where he was from.

The Dave Matthews Band initially backed the driver, who denied dumping the waste before owning up to it. The band went so far as to offer up DNA samples to investigators. Video evidence that police tracked down from security cameras at the nearby East Bank Club left no doubt who was at fault.

• Rundown Podcast: It’s been 20 years since the Dave Matthews Band incident left people in ‘stunned silence’

A number of lawsuits were filed, including by several passengers and Illinois Attorney General Lisa Madigan, who ultimately dropped the suit in exchange for the band’s agreeing to donate $200,000 to state environmental programs.

The band also donated $50,000 each to Friends of the Chicago River and the Chicago Park District, and the city raised its fines for illegal dumping.

Margaret Frisbie, executive director Friends of the Chicago River, said she tried to reach out to the band through an intermediary to see if Dave Matthews would be willing to use the 20th anniversary to help the environment.

She wanted to see if Matthews would donate a minute of his time in the form of a Zoom call that would be auctioned off at the nonprofit’s annual Big Fish Ball, or record a short video to be played at the gala.

“The incident is woven into the city’s pop culture fabric, and the anniversary seemed like an opportunity to emphasize that the world has to protect our natural resources, but it didn’t work out,” Frisbie said of the effort.

The Chicago Architecture Center, which continues to host river tours along with Chicago’s Little Lady operator Chicago’s First Lady, provided a joint statement on the anniversary that read in part:

“There is certainly no joy in reliving the 2004 event that traumatized our passengers and crew. ... We choose to not let what took place that day diminish our contributions in showcasing the city we love with the world.

The Dave Matthews Band didn’t return a message seeking comment.

The Sun-Times’ first report on the Dave Matthews Band tour bus incident in 2004.

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The Dave Matthews Band Chicago River Poop Incident, 20 Years Later: ‘Our Generation’s O’Leary’s Cow’

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RIVER NORTH — Dave Matthews’ relationship with Chicago is a storied one. Earlier this summer, Matthews was spotted in the infield seats at Wrigley Field, with an unsuspecting fan in a DMB T-shirt sitting in the bleachers, nary the wiser. 

Dave Matthews is shown on ESPN in the infield seats at Wrigley Field. ESPN then shows a guy in a Dave Matthews Band shirt in the bleachers. "OH MY GOSH! IF ONLY THAT GUY KNEW! Somebody just tell him… Bring that beer to Dave Matthews!" – Boog Sciambi ⚾️🎶📺🎙️🤣 pic.twitter.com/X6wsD6pZtR — Awful Announcing (@awfulannouncing) June 24, 2024

But not every Chicagoan has had such a near-miss with Dave.

Thursday marks the 20th anniversary of a moment that, for fans of Chicago music culture, will live in dysentery: The day a Dave Matthews Band tour bus dumped 800 pounds of feces into the Chicago River, offering an unpleasant shower to the unsuspecting passengers of a tour boat passing underneath.

On the afternoon of Aug. 8, 2004, a charter bus belonging to the Dave Matthews Band drove across the Kinzie Street Bridge and emptied its septic tank over the Chicago River. The sewage ran through the metal grates of the bridge, and rather than landing in the water — itself a health hazard — it splattered onto more than 100 people on a sightseeing boat operated by the Chicago Architecture Foundation.

Brett McNeil, a reporter for the Tribune at the time, was in the splash zone that day, taking an architectural tour on his day off with his then-girlfriend.

“I sat toward the bow of the boat, so I didn’t have a very good view of what was happening to us,” he recounted to Block Club. 

In the moments before the bus passed over the boat, McNeil thought the noise was a street sweeper or a truck the city uses to water flower beds. But as the brown water splashed down — hitting McNeil in the arm — there was an immediate stunned silence, then eventual panic from the passengers as the Port-a-Potty smell began to make itself known, McNeil said.

“The docent didn’t grasp what was happening in real time,” McNeil said. “I think he thought we’d been hit with water. Then a passenger from the back of the boat said, ‘That’s not water, buddy; that’s urine.’”

From there, there was a “Monty Python skit-like” vomitorium as the passengers reeled from the brown slurry that had passed overhead, McNeil said. A motorcyclist with his helmet upturned had to dump it out overboard. One woman sitting near him said she’d had her mouth open. McNeil, his girlfriend and several others raced below decks to huddle over the air conditioning vents; from inside the glass enclosure, he could see people retching and puking over the side of the boat. 

The boat raced back to dock, ignoring the wake zone so the filthy, stunned passengers could disembark.

“I remember people standing on the dock saying, ‘How are we going to drive home?’” McNeil said.

Only a few days later, the two Econoline buses in question were identified while parked outside the Peninsula Hotel, where Dave Matthews Band was staying during their Chicago stop. The rest is Chicago history.

The culprit turned out to be the band’s tour bus driver, then-42-year-old Stefan Wohl, who pleaded guilty to charges of reckless conduct and discharging contaminates to cause water pollution. He got hit with 18 months on probation, 150 hours of community service and had to pay a $10,000 fine to Friends of the Chicago River. 

The incident has continued to capture the imaginations of Chicagoans many years later, with social media posts and homespun signs along the Kinzie River Bridge commemorating the spot of the sloppy scenario. In 2023, Riot Fest put up a commemorative plaque honoring the occasion as a sort of “official remembrance.” 

This Thursday, Hideout Chicago, 1354 W. Wabansia Ave., is hosting a sold-out Don’t Drink the Water dance party to celebrate the event. 

Not everyone is on board with the remembrance. The Chicago Architecture Foundation, the organization that runs the river tours, gave Block Club the following response when asked for comment:

“There is certainly no joy in reliving the 2004 event that traumatized our passengers and crew, as well as Chicago’s First Lady, a family business, and the CAC, a non-profit organization. Together we have provided acclaimed architecture river cruises on Chicago’s waterways for more than 30 years, and we choose to not let what took place that day diminish our contributions in showcasing the city we love with the world. Out of respect for all who were affected, we will not provide any additional comment. Thank you for your understanding.”

Margaret Frisbie, executive director of the nonprofit Friends of the Chicago River, remembers the incident well; as deputy director at the time, she was running a canoe race on the Chicago River that day.

“We were horrified by what happened to those people on that boat, because it’s an unimaginable experience,” she said.

Why the fascination? “The hate for Dave Matthews and the love for poop jokes,” mused Jeremy Scheuch, creative director for Riot Fest. One of his first duties (heh) in 2016 was to write an article on the event , and he remembers it having more views than anything the Riot Fest website had posted before then, even above announcements and lineups. 

To compensate for the incident, Dave Matthews Band donated $50,000 to the Friends of the Chicago River, which the group has since used to start an endowment to further its public policy work to clean up the river and make it more accessible to Chicagoans. 

But many Chicagoans see the fecal fable as an erstwhile badge of honor for the city’s rough-and-tumble culture.

“People who live in Chicago take pride in the dumbest, greatest s—,” Scheuch said. “It’s like Malört: It’s horrible, but it’s ours.”

“It’s scatological and completely harmless,” McNeil said. “How many Chicago stories like this are there? This is our generation’s O’Leary’s cow — an absolutely livable civic touchstone of no consequence.” 

Some Chicagoans have even taken to conspiracy theories, like imagining Dave Matthews himself pulled the lever. But McNeil takes umbrage to those ideas.

“I couldn’t care less about Dave Matthews Band, but I think he personally and the brand of his jam band have paid kind of an unfair price for a contractor’s f—-up,” McNeil said. “It’s like making Ford pay a significant price for the f—ing Bronco chase.” 

For Frisbie, the story of the Chicago River incident is a story of positive change.

“Twenty years ago, people were used to thinking of the Chicago River system as polluted and were more accepting of it, whereas today that’s no longer true,” she said. 

Frisbie has seen the incident used as a teaching moment for Chicagoans about the need to treat our rivers with care.

“What we realized at the time was that that kind of treatment of rivers, when people think no one’s watching, is more common than people think,” she said. 

Frisbie, like others, hopes the event continues to prove a testament to maintaining the sanctity of the city’s rivers for years to come. 

After all, as Matthews once sang, the future is no place to place your better days.

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Clint Worthington

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Hop On Hop Off in Moscow

City Sightseeing: Moscow Hop-On, Hop-Off Bus Tour

• The Bus Tour offers unlimited 360° panoramic views of main sights of Moscow.
• Access to audio-guide in 10 different languages which enables to know about Moscow’s history and traditions.
• The three-bus tour routes and 40+ stops around Moscow completes the trip. Draw an itinerary to explore the city on your own.
• There can be a boat tour and bus tour to enjoy panoramic views of Moskva River.
• Smartphone Voucher Accepted. (No need to print)
• 24 / 48-Hours Hop-on Hop-off Bus Ticket
• Red Line Audio Guide: Russian, English, German, Spanish, Italian, French, Chinese, Arabic, Portuguese, Farsi
• Green Line Audio Guide: Russian, English, German, Spanish, Italian, French, Chinese, Arabic
• Orange Line Audio Guide : Russian English, German, Spanish, Italian, French
• Guided walking tour
• Boat Tour (If option selected)
• Red Route: Schedule: 10:00 - 18:00 , Loop: 60 Minutes, Frequency: 15 Minutes
• Green Route: Schedule: 10:00 - 18:00 , Loop: 120 Minutes, Frequency: 30 Minutes
• Orange Route: Schedule: 10:00 - 18:30 , Loop: 140 Minutes, Frequency: 30 Minutes

Wheelchair Access, Heating Please note that face masks must be worn on board the bus. Orange Route is temporarily suspended   

Operational Details: Walking Tour

• Daily at 10:45 a.m.
• Duration: 2 hours 30 minutes
• Meeting point: next to the monument to Saints Cyril and Methodius (Kitay-Gorod metro station)

Capital River Boat Tour

• May - October: from 11:30am to 6:30pm (Subject to change)
• Duration: 60 minutes
• Departure Point: Zaryadye Park Pier
• You must cancel your booking at least 24 hours before the start time of the activity/experience to get a complete refund.
• If you cancel your booking less than 24 hours before the start time of the activity/experience, you will not be reimbursed.
• Any modifications made less than 24 hours before the start time of the activity/experience will not be allowed.
• The cut-off times are determined by the activity/experience's local start time.
• This activity/experience is weather dependent. If it is cancelled due to inclement weather, you will be given an alternate date or a full refund.

Hop On Hop Off Moscow Bus Tours

Moscow, the capital of Russia, is the largest and the most populous city in the country. Present on the banks of the Moskva river, this city serves as the cosmopolitan hub of the country. Carrying  871 year old rich history, this city has played an integral part of Russia’s development and therefore plays an integral role in all the aspect. Majority of the population of Russia lives in Moscow, and the city is responsible as the scientific, historical, political and architectural hub in the region. Moscow is a blend of the old and new Russian culture. The Kremlin complex in the center of the city holds the cultural and historical values of the city. Moscow was also the capital and most important part of the USSR and thus holds many gems throughout the city from that era. Not only that, but the city also brags of timeless elements from the Tsars and other rulers who ever ruled Russia. Moscow has been a hub of many social ideologies and home to popular poets and artists. When in Moscow don’t miss out The Moscow Kremlin, the colorful St. Basil’s Cathedral, the symbolic center of Russia as the Red Square and Lenin's Mausoleum, which also serves as the resting place of Vladimir Lenin and his body has been preserved there since 1924.

Other Cities in Russia

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For groups of 12 or more, you may send us an inquiry at [email protected]. Although we do not guarantee bulk deals for all our tours, there are some tours for which we can offer discounted pricing. Ordinary hop-on-hop-off bus tickets are entitled to group savings. Attractions, pass items and combo tickets aren't.

Due the nature of this type of tour and varying demand, group travellers should be aware that there is no guarantee that the group will be able to travel altogether as the available seats vary from stop to stop and depends on demand each day. The group may need to split up and/or wait for the next bus(s).

As, we cannot guarantee that the group shall be able to travel together as one group, therefore we will reduce the group size down to 4-5 smaller groups per ticket (depending upon group size).