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The 16 best chicago tours for 2024, according to reviews.

Foodies, architecture buffs and historians alike will appreciate these tours of the Windy City.

The 16 Best Chicago Tours for 2024

Alejandro Reyes | Choose Chicago

One of the best ways to sightsee your way through a new city is with the help of a local. With this in mind, U.S. News rounded up some of Chicago 's best guided tours. Whether you're sailing past Willis Tower on a river cruise or sampling some of Chicago's best deep-dish pizza on a foodie excursion, you'll gain a cultural and historical understanding of the Windy City during these tours.

Editor’s Pick: Wendella Boats – Chicago River Architecture Tour

Price: Adults from $44; kids from $20 Duration: 1.5 hours

U.S. News independently paid to send Cortney Fries , an award-winning writer based in Chicago, on this tour to provide readers with an unbiased, first-hand perspective of what to expect. The Wendella Boats Chicago River Architecture Tour was selected by our team as an Editor’s Pick thanks to its popularity and favorable user reviews.

Cruise three branches of the Chicago River taking in views of famous Chicago landmarks while a knowledgeable guide provides an overview of the architecture and interesting lessons in Chicago history on this popular boat tour. For instance, did you know that the Lyric Opera House was built in the shape of a giant throne? Learn how the Chicago River is the only natural river reversed by humankind. View iconic buildings, such as the Merchandise Mart and Willis Tower. Hear about what the four stars on the Chicago flag represent, the legend of the O’Leary cow starting the Great Chicago Fire, the statue atop the Chicago Board of Trade and Chicago’s famous drawbridges.

Refreshments and snacks are sold on board. Sit on the top deck to listen to the live tour with unobstructed views, but bring a jacket or sun hat if it’s cool or sunny. Climate-controlled seating is offered below, as are restrooms. Tours are generally available daily beginning at 9:30 a.m., with multiple departures throughout the day and evening. Short on time, or have kids in tow? Try the 45-minute version of this architecture tour.

Cortney Fries

Why we love it:

• Learn about the dense variety of architectural styles along the Chicago River without having to navigate crowded streets.
• Engaging guides make for a memorable experience and provide glimpses into different parts of the city you might want to explore more during your trip.
• Tours depart from Michigan Avenue near the Wrigley Building. Give yourself plenty of time to find parking and also enjoy ample shopping and dining options nearby.

– Cortney Fries

Check prices & availability on:

Chicago Architecture Foundation River Cruise

Price: From $54 Duration: 1.5 hours

The Chicago Architecture Foundation's River Cruise ferries passengers along the Chicago River as docents from the Chicago Architecture Center regale them with the stories behind more than 50 notable buildings. The volunteer docents repeatedly win high praise from reviewers for their in-depth knowledge of the city's history and its structures. Many reviewers called this the best thing to do in Chicago. The cruising vessels, part of the Chicago's First Lady Cruises fleet, can carry up to 250 people and boast full-service bars and open-air upper decks.

For a different perspective of the city's iconic architecture, consider the twilight sailing, which costs a few dollars extra. For an additional $5, you can also gain admittance to the Chicago Architecture Center (which usually costs $14 on its own).

Chicago Food & City Tours – Gateway to the West Loop Food Tour

Price: Adults from $85; kids from $50 Duration: 3 hours

This foodie tour centers on the West Loop neighborhood's incredible dining scene, and provides insider insights to the area's evolution from a meat-packing and warehouse district to the Restaurant Row of today. Foods you may sample include doughnuts, hamburgers, pizza and cupcakes. Guides regularly earn five stars from travelers for their insight and enthusiasm. Reviewers find the tour worth the price for the generous amounts of food provided. What's more, group sizes are restricted to 16 people and tours do not involve extensive walking (a little more than half a mile).

Tours are offered Sunday, Tuesday and Thursday at 1 p.m. Hungry for more? The company also offers a tour inspired by the TV show "The Bear," which is set in Chicago, as well as a tour all about the city's most iconic foods.

Absolutely Chicago Segway Tours – Chicago Lakefront Museum Campus Tour

Price: From $65 Duration: 2 hours

The Chicago Lakefront/Museum Campus tour offered by Absolutely Chicago Segway Tours showcases many of the city's most popular attractions along its 5- to 6-mile route, including Millennium Park (the starting point), Grant Park , Monroe Harbor, the Field Museum , Shedd Aquarium , Soldier Field and the Adler Planetarium. Participants applaud tour guides for their expertise and professionalism and say this is a safe, fun way to see the city's top sights in a short amount of time.

Note that riders must be at least 12 years old to participate. Tours are available multiple times a day from spring through autumn. The company offers several other Segway tours, some centered around other parts of the city or with specific themes like architecture, crime and ghosts.

Inside Chicago Walking Tours – Dazzling Interiors of the Loop

Price: Adults from $30; kids from $25 Duration: 2 hours

Many travelers are familiar with Chicago's distinct architecture, but its equally captivating indoor spaces are not as well known. This tour reveals interior architectural details that visitors might otherwise miss. Guides take participants inside some of Chicago's most stunning buildings to admire elements like a gilded 80-foot-high ceiling, art deco lobbies, early Frank Lloyd Wright designs and rooms with stained-glass mosaics. Reviewers describe this tour, which involves about 1 1/2 miles of walking, as an informative and entertaining way to learn about the history of Chicago and its diverse, distinctive buildings. Others said this tour is great for first-time visitors and locals alike.

Tours operate Thursday through Monday at 11 a.m. Once you've toured all of the buildings at the street level, consider the company's Chicago Pedway tour, which tours the downtown underground tunnels that residents use to stay warm and dry during bad weather.

Courtesy of Bobby's Bike Hike Chicago

Bobby's Bike Hike Chicago – Bikes, Bites & Brews Chicago’s Signature Dishes Bike Tour

Price: From $85 Duration: 4 hours

This triple threat tour combines bicycling, food and beer. The 13-mile ride traverses the Gold Coast, Lakeview, Wrigleyville and Lincoln Park neighborhoods with stops for pizza, beer, cupcakes and hot dogs. Reviewers say the pace of the tour is easy and applaud the guides for their fun and engaging commentary. Others said they learned a lot about Chicago, calling the ride entertaining and educational.

Tours are generally offered daily at 11:30 a.m. and 5:30 p.m. (except during the winter). Note that the evening tour mostly bikes around downtown Chicago. If you're interested in venturing beyond downtown, book the morning tour. Tickets cover the cost of the bike rental as well as food and drinks. Participants must be at least 21 years old. If you're traveling with kids, try the company's Family & Food Bike Tour of Top Attractions.

Chicago Pizza Tours – Original Chicago Pizza Tour

Price: Adults from $75; kids from $45 Duration: 3.5 hours

Enjoy a crash course in what makes Chicago pizza so iconic on this delicious tour. You'll visit four independently run neighborhood pizzerias and sample six or more slices of pizza in a variety of styles (deep dish, tavern, artisanal and Neapolitan, to name a few). You'll meet downtown for your first slice before boarding a bus to neighborhoods like Lincoln Park, Lakeview and Bucktown. Reviewers compliment the informative and entertaining tour guides and insist that the tour is about more than just pizza, highlighting the various aspects of Chicago history, architecture and culture that's spotlighted during the nearly half-day excursion.

Tours run Saturday and Sunday at 11 a.m. The company also offers pizza crawls of downtown and Bucktown.

Chicago Gangsters and Ghosts Tour

Price: Adults from $35; kids from $17 Duration: 2 hours

If you're interested in the darker side of Chicago history, specifically its gangsters and ghosts, consider this walking tour. With a historian leading the way, you'll stroll for about 1.5 miles around the Loop – once known as the "Vice" district in the 1920s and '30s for its rampant partying, speakeasy saloons and underground tunnels used by bootleggers. Participants rave about the guides for their storytelling abilities and say the length of the tour is perfect for when you need a break from the city's more touristy activities.

Tours run four times daily beginning at 11 a.m. The company also runs a Gangster Food Tour that highlights some of the city's most iconic foods like deep-dish pizza and hot dogs, as well as the restaurants that once served as some of Al Capone's old hideouts.

Courtesy of Big Bus Chicago

Big Bus Chicago – The Big Loop - Red Route

Price: Adults from $49.50; kids from $35.10 Duration: 2 hours

Big Bus Chicago's hop-on, hop-off tours invite tourists to tailor their sightseeing excursions to their preferences by allowing them to spend as much time as they want at any of the 11 stops on the company's red route. Tour-takers can "hop off" a bus and explore any of the top attractions featured along the way, such as Skydeck Chicago , Navy Pier or Millennium Park, and then "hop on" a later bus. If you don't get off the bus, the entire route takes about two hours. Your ticket is valid for 24 hours, so you can hop on and off as much you please.

Buses run every 30 minutes starting at 10 a.m. daily and include prerecorded commentary in both English and Spanish. Reviews from recent travelers were mixed: Some riders loved the convenience of the bus, saying it puts you within easy walking distance of the city's best attractions, but others were disappointed with the quality of the prerecorded commentary and said you should try to seek out the few busses that feature a live guide. If you want to ensure you'll have a live guide on your bus, consider booking the nonstop, 90-minute Sunset Live Tour, which is offered from May to October.

Secret Food Tours: Chicago 

Price: Adults from $79; kids from $69 Duration: 3.5 hours   Follow a local foodie around the Loop district for what the company calls a "moving feast." You'll make six stops to sample some of the city's most notable dishes, including deep-dish pizza, gourmet popcorn, a Chicago-style hot dog, an Italian beef sandwich and a brownie (which was purportedly invented in Chicago). What's more, there's a secret dish revealed the day of the tour. Plus, tours are capped at 12 participants to ensure an intimate experience. Reviewers say guides do an excellent job of highlighting not only Chicago's distinct food scene, but also its history and architecture. They also advise that you'll want to come hungry as the portions are generous.

Tours operate daily at multiple times; the earliest tour departs at 11:30 a.m. The company can also arrange private tours.

Underground Donut Tour – Chicago: Downtown Tour

Price: Adults from $55; kids from $50 Duration: 2 hours   Come hungry for this food tour, which visits four of the best doughnut shops in the city, including Doughnut Vault and Do-Rite Donuts. As you nosh on the sweet treats, your guide will share the history of each shop and the history of doughnuts in Chicago. Travelers recommend this tour for the knowledgeable, engaging guides and the delicious selection of doughnuts. They also say you'll learn about much more than doughnuts, as guides share historical tidbits about Chicago and recommendations for how to make the most of your trip.

Tours operate daily at 10 a.m.; additional 9 a.m. and noon tours are offered Wednesday through Sunday.

Graham Chapman | Choose Chicago

Urban Kayak Chicago Riverwalk – Historic Chicago Tour

Price: From $55 Duration: 2 hours

For a "duck's-eye," up-close view of the city, take Urban Kayak's Historic Chicago Tour. Starting at the Riverwalk , tour-takers paddle their kayaks on the main branch of the Chicago River with periodic stops at points of historical interest, where guides provide information regarding the city's famed architecture. Reviewers say this is a great experience, even for beginners, and recommend the tour for travelers looking for a unique alternative to the popular architecture river cruises. Meanwhile, others note that the experienced guides are skillful at navigating boat traffic.

Tours are offered multiple times a day spring through early fall. Urban Kayak also offers kayak rentals and paddleboarding classes.

Check prices & view availability on:

Shoreline Sightseeing – Skyline Lake Cruise

Price: Adults from $35; kids from $17 Duration: 45 minutes

If you've already taken an architecture cruise on the Chicago River and can't get enough of the views, consider this boat tour. Shoreline Sightseeing Skyline Lake Tours offer unrivaled views of Chicago's skyline, and many photo opportunities, via cruises along the Lake Michigan shoreline. The 6-mile trip provides views of notable landmarks, such as the John Hancock Center, the Willis Tower (aka the Sears Tower), Adler Planetarium and the Field Museum, as well as an informative prerecorded commentary. According to reviewers, these iconic buildings are much more visible from the water than they are on the street, though a few warned that it's difficult to hear the recorded commentary from certain areas of the boat (sit in the middle of the boat if you want to ensure you can hear the narration).

Travelers can purchase drinks at the onboard cash bar. Tours are offered daily spring through autumn (weather permitting) and depart from Navy Pier. Shoreline Sightseeing also offers architecture cruises along the Chicago River.

Ken Flisek | Courtesy of Tall Ship Windy

Tall Ship Windy – Chicago Skyline Sail

Price: Adults from $49; kids from $39 Duration: 75 minutes

Tall Ship Windy's Chicago Skyline Sail features views of the city from the deck of a 148-foot, four-masted schooner. Reviewers tout the remarkable views of the city's impressive buildings and, weather-permitting, the special experience of being able to actually sail and not rely on the boat's motor. What's more, tour participants commend the crew members for their professionalism, humor and knowledge of Chicago.

From spring through fall, there are generally four sails daily starting at 1 p.m.; the 1 p.m. sailing focuses on piracy in the Great Lakes and the Caribbean. Tall Ship Windy has a full bar on board (drinks are not included in the ticket price). In addition to daily sails, Tall Ship Windy offers evening cruises timed to the fireworks display at Navy Pier, which occurs on select dates in the summer.

Chicago Crime Tours and Experiences – Chicago Crime and Mob Bus Tour

Price: From $42 Duration: 2 hours

If you're a fan of true crime, you'll be intrigued by this bus tour, which explores the city's most famous gangsters and crime scenes. As you drive in a variety of Chicago neighborhoods, including the Gold Coast, Lincoln Park, the Loop, the Magnificent Mile , Old Town and River North, your guide will share stories and you'll watch historic video footage. The bus tour includes stops at the spots where gangsters like Hymie Weiss were killed as well as the site of the St. Valentine's Day Massacre. It also visits locales associated with Al Capone, Frank "the Enforcer" Nitti and Leopold and Loeb, among others. Reviewers laud the tours for providing a unique angle on Chicago's colorful history and describe guides as entertaining.

Tours are offered multiple times a day. For a longer tour with even more stops, consider the company's Night Crimes Tour.

Check prices & availability:

City Experiences – Chicago Seadog Lakefront Speedboat Tour

Price: Adults from $35; kids from $25 Duration: 30 minutes

Zip across Lake Michigan during this high-speed, narrated half-hour tour. During the ride, you'll see striking views of the Chicago skyline and hear some descriptions of the sights. Visitors praise the crew's knowledge and charisma. They also enjoy whipping along the waves. Keep in mind: The boat is open-air, which means you might get wet. The company also discourages pregnant women and travelers with back or neck sensitivities from participating.

Speedboat rides are offered daily spring through fall. City Cruises also operates a narrated architecture cruise, in addition to brunch and dinner cruises.

You may also be interested in:

• The Best Chicago Walking Tours
• The Best Chicago Segway Tours
• The Best Chicago Boat Tours
• The Best Hotels in Chicago
• The Top Romantic Getaways in Illinois

Tags: Chicago , Travel , food and drink , Vacations , Tours , Illinois Vacations , Midwest Vacations , US Vacations

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The 6 best tours and walks in Chicago

Experience the city's rich history, culture, architecture and attractions on these essential Chicago tours

There are many ways to experience Chicago: by foot, bike, boat, bus, trolley, kayak… So in an effort to keep you on the right path while you're exploring the city, we've rounded up some top-rated Chicago bike tours, walking tours, boat tours and more. These are, in our opinion, the best ways to discover Chicago's best attractions, beautiful buildings , history and culture (not to mention the best  restaurants , craft breweries and the lakefront). Embrace your inner tourist and hit the road on one of these adventures. Keep a couple dollars in the pocket though, there's a whole lot of food and drink to be added on to your adventures. 

RECOMMENDED: The  best things to do in Chicago that locals and tourists will love The best crime tours in Chicago

This article includes affiliate links. These links have no influence on our editorial content. For more information, click  here .

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

Top Chicago tours

1.  big bus hop-on hop-off sightseeing tour.

If you look for flexibility when it comes to sightseeing, this bus tour is your best bet. Choose between a 24 or 48-hour ticket and alight as you please; stepping on for a relaxing ride around the city, and stepping off when you'd like to get up-close and personal with one of the landmarks or attractions. You'll be passing by Willis Tower, Adler Planetarium, Chicago Water Tower, Magnificent Mile and many more must-see sites – with plenty of conveniently-located stops along the way. The route is a loop, so you won't have to worry about straying too far from the starting point. 

Don't miss: A shopping trip at Magnificent Mile or a food pitstop at Navy Pier (or both). 

2.  Chicago Architecture Foundation River Cruise

This Chicago architecture tour is a must for entertaining family and friends from out of town or just orienting yourself to the city’s many architectural wonders. With a knowledgeable docent in tow, you'll cruise along the Chicago River from River City north to Goose Island, taking in stunning, unimpeded views of some of the city's most famous skyscrapers along the way. On the river, you'll take in over 40 landmark buildings, including towers from the Tribune to the Trump. There's a bar too, just in case. Reservations are strongly recommended.

Dont miss:  Drinks from the on-board bar (don't forget to bring cash). 

3.  Lakefront Neighborhoods Tour

If you need a crash course in why Chicago is so damn awesome, this bike tour of the Lakefront should do the trick. Within three hours you'll see Gold Coast mansions, Lincoln Park Zoo and North Avenue Beach. You'll bike approximately seven miles (easy going in three hours) along the Lakefront Trail, admiring the breathtaking skyline sights. You'll also get a little glimpse at Oprah's pad, and of course, the whole affair will enrich both your mind and body. A lovely way to spend a day. Ticket price includes bike, helmet and guide. 

Don't miss:  The chance to marvel at Hugh Hefner's original Playboy Mansion. 

4.  Chicago Pedway Walking Tour

After you've gotten an overview from the river, get inside some of those buildings with this 90-minute walking tour. Making use of the Pedway, the tour is almost completely indoors, making it a good option for winter visitors (or stormy summer days, equally common). Guests share iPads loaded with historic photos, videos and archival maps for additional context. The guides are known to be a witty bunch too, so it's a good time all round. Reservations are required.

Don't miss:  You'll get to see bits of where Dark Knight was filmed, which will suit the batman fans among you. 

5.  Chicago Helicopter Experience

No Chicago tour will take you higher than the Chicago Helicopter Experience, which offers aerial views of the city's skyline. You'll board a chopper on the outskirts of Bridgeport and fly up the coast of Lake Michigan to Montrose Harbor and back in about 15 minutes. The cost of the flight might seem a little steep, but the photo opportunities are priceless. When else have you seen such a tall city, a wonderful lake, and so much more from a birds-eye view, ever? Exactly. It's a doors-open experience too, to get the adrenaline pumping. 

Don't miss: A lesson in Chicago's rich architecture and architect Frank Lloyd Wright. 

6.  Chicago Style Food Tour

If you want to fill up on iconic Chicago foods while you're in town, look no further than this epic three-hour guided adventure. Though the stops change occasionally, expect to nosh on deep-dish pizza, Chicago-style hot dogs (poppy seeds galore), handmade chocolates and so much more. Have a light breakfast, is our advice. Consider it your primer to Chicago's most notable food groups. The number of people per tour is pretty small too, so you can really geek out when asking the questions.

Don't miss:  The chance to ask your guide for some top dinner recommendations. 

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Private tours in Chicago

Private Chicago Walking Tour

Get the chance to visit one of the most incredible cities of the United States: Chicago. Walk around it streets alongside a private official tour guide. Visit the most important and emblematic monuments and sites with this private walking tour. ... Learn more

Private City Tour of Chicago

Make the best of your time in Chicago and visit all the most important places and monuments with this private city tour of Chicago. Get the chance to learn about the history and culture of this incredible city with a professional guide and private driver. ... Learn more

Private Tour to Milwaukee from Chicago

Enjoy to the fullest your days in Chicago and come with us on this private full day tour to Milwaukee. Visit the most incredible museums, monuments and parks with a local tour guide comfortable in a private luxury vehicle with separate driver. ... Learn more

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Guide to Chicago in the Fall

Do you want to know the best things to do in Chicago in the fall?

There are many seasonal activities at this time of year, and we have compiled a list of our favorites.

Whether you are looking for fall foods and brews, family-friendly fall activities, or spooky activities, there is something for everyone in Chicago. 

We encourage you to check out the full guide, or you can jump to a specific section here: 

• Family Friendly
• What to Pack
• Holidays & Festivals
• Free Tours by Foot

TOP 10 FALL ACTIVITIES IN CHICAGO

This is a Top 10 list of things to do in Chicago this Fall. For more ideas on popular things to do in Chicago, check out our posts on bus tours and walking tours of the city.

Some of the items listed in this post are included for free with the purchase of a tourist concession pass . 

1. Take a Tour!

The best way to get out and enjoy the cool breeze in Chicago this fall is to take a tour with a local guide.

Free Tours by Foot offers walking tours of Chicago of various neighborhoods, including the Loop, the Riverwalk, and specialty tours like an evening Ghost Tour to learn about Chicago's Haunting History.

One of our most popular autumn tours is our Lincoln Park Gangster & Blues tour, offering fun history while walking along beautifully fall-colored leaves on the trees.

Explore Chicago by Boat, Bus, Segway, and Bike

If you’re not up for walking, there are many ways to explore the city.

• Chicago Boat Tours & Cruises
• Chicago Bus Tours
• Segway Tours

2. Autumn Farm Pop-Ups and Farms

Nothing says fall quite like pumpkin patches, corn mazes, and apple picking.

Check out some local pop-ups and nearby farms for hayrides for the kids and apple cider for the adults.

• Night of 1,000 Jack-o'-Lanterns
• Jack's Pumpkin Pop-Up

Local Farms

• Jonamac Orchard (Apple)
• Prairie Sky Orchard (Apple)
• Honey Hill Orchard (Apple)
• Goebbert's Pumpkin Patch
• County Line Orchard (Apple and Pumpkins)

For more fun things to do with kids, check out the Kids section below.

3. Oktoberfest

This German tradition continues for another year in the Windy City.

Grab some cold beer, bratwurst, and pretzels as you enjoy the authentic German bands and culture. 

We have a guide to drinking in Chicago - featuring the best rooftop bars , historic bars, speakeasies, and more.

But, for a true Oktoberfest experience, go to the German-American Oktoberfest in September.

4. Catch a Concert

There are plenty of great shows going down in Chicago this fall.

Going to a concert is a great way to cap off an evening after spending the day touring Chicago.

Some big names coming to Chicago this fall:

• My Chemical Romance - Sept. 16
• Kid Cudi - Sept. 16
• Nine Inch Nails - Sept 18
• Keith Urban - Sept. 24
• Mary J. Blige - Sept. 25
• Pet Shop Boys - Sept. 30
• Jack Harlow - Oct. 1
• Gorrilaz - Oct. 3
• Harry Styles - Oct. 6, 8-9, 13-15
• B52s - Oct. 7-8
• Lizzo - Oct. 16
• Bow Wow - Oct. 22
• Carrie Underwood - Oct. 22
• Carly Rae Jepsen - Nov. 5
• Smashing Pumpkins - Nov. 5
• Paramore - Nov. 9 
• Dave Matthews Band - Nov. 15

For a list of more things to do at night in Chicago this Fall, check out our Things to Do at Night post.

Chicago also has some free and family-friendly concerts and festivals, which you can check out in the Festival section below.

5. Attend the Theater - Musicals and Comedians

Chicago has an incredible Theater District , which you can not only visit to see a show but also take a tour!

There are a number of incredible performances hosted in Chicago this fall, from the very famous Wicked  musical to incredible stand-up comedians like Kevin Hart and George Lopez .

To explore the history of the area on one of our pay-what-you-like tours, click to view our calendar here . 

We encourage you to browse the performances coming to Chicago here to find a performance that's perfect for you!

Chicago boasts a number of great professional sports teams.

The weather in Chicago in December makes it favorable to enjoy various sports activities.

Depending on what time of year you're visiting, there's bound to be a great game going on.

Fall means football and you can watch "Daaa Bears" at Soldier Field.

Football   (August through December)

• Chicago Bears
• Northwestern Wildcats
• Catch the cheap preseason tickets of the Chicago Bulls

Ice Hockey  (October through April)

• Chicago Blackhawks
• Chicago Wolves

For more ideas on family-friendly things to do in Chicago, check out the section below .  

7. Halloween

Time to get spooky for Halloween!

If you're too old to go trick-or-treating, you can still get dressed up in your favorite costume and come out for our Haunted History and Ghost walking tour.

Explore the haunted parts of the city on the day the ghouls and ghosts are out.

Our ghost tours fill up fast in the fall. Reserve early! Click here to reserve your spot. 

Attend the Arts in the Dark Halloween Parade on State Street before you wander down the Congress Hotel for the  Haunted Halloween Ball for the big kid in you on Halloween night. 

You can also celebrate Halloween in the parks !

From Halloween parties to haunted houses and the annual Pumpkins 5K Run & Kids Spooky Sprint, there's something for everyone at these free events.

For more kid-friendly Halloween activities, check out our kids' section below. 

8. Thanksgiving

Whether or not you have family here for Thanksgiving, Chicago will make you feel at home during the holidays.

With lots of things to do solo or with loved ones, you'll feel thankful for being here in the Windy City. 

The Magnificent Mile Light Festival is an annual event with beautiful lights and a series of family-friendly events for everyone to enjoy.

For a full schedule, click here  to plan your visit. 

Chicago's Christkindlmarket has been around since 1996 and opens in mid-November and features German goodies, such as spiced wine, German beers, desserts, sausages, and potato pancakes. 

There are also vendors selling festive goods like ornaments, nutcrackers, and toys. 

For more things to do for Thanksgiving in Chicago, click here . 

9.  Open House Chicago

TBD for 2024. Last year date: October 14-15

Ever walked around Chicago wishing you could just walk into and see the insides of its incredible buildings? Well, you can!

Once a year the city opens up to the public for  Open House Chicago  to explore the incredible architecture from the inside.

You'll be able to go behind the scenes to more than 250 buildings in Chicago during this free public festival, from skyscrapers to private residences.

Don't want to do it alone? Join us for a pay-what-you-like architecture tour of Chicago to learn about the cityscape.

These tours include:

• The Birth of the Skyscraper
• North Loop and Millennium Park Tour
• Riverwalk and Chicago History Tour
• The Magnificent Mile Tour
• West Loop Tour

In addition to our walking tours, there are other walking tour companies that offer excellent architecture tours.

Another popular option is to take an  architectural boat cruise . There are even architectural  tours by bus  as well as Segway.

10. Look into a Tourist Concession Pass

Visitors who are working with a budget should think about getting a Chicago tourist pass.

These services provide heavy price cuts at some of the most popular attractions in the city.

Here are a few of the sites you can visit with various concession passes, which include some great fall activities such as:

• Navy Pier Ride Pass
• Architecture River Cruise
• Bike Rentals
• Shedd Aquarium
• Skydeck Chicago
• The Field Museum
• Museum of Science and Industry
• 360 Chicago Observation Deck
• Adler Planetarium
• Art Institute of Chicago

These are just a few of the activities you can enjoy. If you plan to visit even a few of these attractions, you could easily end up saving a lot of money over general admission prices.

For more details, make sure to read our full post covering Chicago tourist passes .

11. Explore Morton Arboretum

Discover the beauty of Illinois as you wander through the scenic paths of Morton Arboretum.

As the leaves change, immerse yourself in the vibrant colors of fall. Don't miss the Scarecrow Trail, where creativity meets nature.

After your exploration, quench your thirst at the Cider and Ale Festival.

Let nightly spirits lift your mood and enjoy the refreshing taste of autumn.

12. Adventure Awaits at Richardson Adventure Farm

Looking for a grand adventure in Glencoe? Head to Richardson Adventure Farm, renowned for having the world's largest corn maze.

Navigate the intricate pathways and masterpieces carved into the corn.

When you complete your maze journey, reward yourself with some food truck delights.

13. Lights and Delights at Navy Pier Pumpkin Lights

Chicago Architecture Center recommends a visit to Navy Pier for the mesmerizing Pumpkin Lights display.

As the evening descends, the pumpkins illuminate the pier, casting a warm glow that contrasts with the cool fall air.

And while you're there, hop on the iconic Ferris Wheel for an elevated view of the city.

Don't forget to check your inbox for the newsletter with special free admission offers.

14. Spooky Thrills at the 13th Floor Haunted House

Brace yourself for a heart-pounding experience at the 13th Floor Haunted House.

Located near Schiller Park, this haunted attraction promises chills and thrills.

After you've had your share of scares, wind down at Goose Island for a calming brew.

15. Dive into Flavors at the Chicago Food Truck Festival

Come hungry to the Chicago Food Truck Festival. With a vast array of choices, from fun carnival games to exciting ax throwing, the fun never stops.

As you taste the delicious treats from different food trucks, pause to appreciate the culinary creations in front of you.

If you're keen, join the ale festival and try out some local beverages.

THINGS TO DO WITH KIDS IN THE FALL

Many of our Top Ten are great activities for children, like going to Navy Pier, but check out our post about Family Friendly Activities in Chicago for a more complete guide. 

Below you will find a couple of other options to keep your children entertained this season!

Trick-or-treating with kids on Halloween is a must!

Try a different neighborhood this year, as some communities have a whole host of activities for kids.

• Night of 1,000 Jack-o-lanterns at the Chicago Botanic Gardens is a must-do for the whole family. They have an entire calendar of spooky, educational fun .
• Ravenswood Manor: check out this historic district to admire the houses as well as collect candy. In the past, it's also won the reputation of the best neighborhood to trick-or-treat in.

Trick-or-treating not your thing? Go to the zoo!

On October 26, Lincoln Park Zoo hosts the very popular annual Spooky Zoo , an event that hosts a number of free activities for kids of all ages. 

Thanksgiving Parade 

The annual Thanksgiving Day Parade can't be missed!

Come out to State Street to see Santa Claus and Ronald McDonald in the lineup while tapping your feet to the tunes of marching bands. 

The parade begins at 8 am and runs until 11 am. Come out early to grab a good spot!

For more ideas of things to do in Chicago for Thanksgiving, check out this link . 

Fall Fest 

The Lincoln Park Zoo is hosting Fall Fest , a celebration of fall running from Sept.27-October 27, Friday-Sundays.

The event is free and guests can enjoy viewing the animals, taking their picture with a giant pumpkin, and delicious snacks.

While a lot of activities are free, there are ticketed events as well, like a corn maze, inflatable obstacle course, and more!

For more fall festivals to enjoy with the whole family, check out our festival section below. 

Museums are a great way to spend time inside on a chilly day!

Chicago has a number of great museums, many of which are free .

Some paid museums have free days, such as the Chicago Children's Museum . 

PACKING GUIDE FOR FALL IN CHICAGO

Packing to go to a city you've never been to can feel daunting- how much is too much?

There's also the fear of meeting unexpected weather and not having packed something essential.

Below are some FAQs about packing we want to answer for you:

• Does it rain a lot in the fall?  September and October have the lowest number of rainy days in the year, so while you should bring rain gear in case the forecast calls for it, you shouldn't have to worry about lots of dreary, rainy days on your visit to Chicago in the fall.  
• What to pack:  Temperatures in Chicago begin to dip in the fall and can get a bit chilly. Pack light jackets and sweaters and comfortable, warm shoes like boots. 
• Be sure to bring water with you.  A lot of the public parks have removed water fountains due to health concerns, so bringing water along prevents you from having to buy expensive water in shops and keeps you hydrated.
• Going out for a drink or nice restaurant in the evening?  If you've been walking around outside all day it might be best to pack along a nice change of clothes. Most places in Chicago are pretty casual in dressing, but if you're  going out at night  to somewhere ritzy like a speakeasy, dressing up a bit is best.

We have a  monthly post  section below if you want to read up more on the specifics of the weather to better decide what clothes to bring on your Fall trip to Chicago.

HOLIDAYS & FESTIVALS

Most Chicago festivals are free to attend and we have LOTS of them throughout the year.

There are food festivals, beer festivals, tequila festivals, music festivals, and art festivals. There is a fest for every type of visitor. 

Below is a list of our most popular fall festivals:

• Lincoln Square Ravenswood Apple Fest
• Harvest Festival at North Park Village Nature Center

FAQ - Frequently Asked Questions

Is chicago cold in the fall.

While Chicago experiences fall foliage and vibrant fall colors, the city can get a bit chilly during the autumn months.

This fall foliage and the cold weather make it an excellent time of year to visit Chicago.

When does it start getting cold in Chicago?

Chicago starts feeling the cold around the time when apple orchards open and apple cider donuts become popular, usually in late September.

When does it snow in Chicago?

Snow in Chicago typically starts when the harvest maze is closing and scarecrow trail events wind down, often around November or December.

We have a full post on when it snows in Chicago .

What should you wear in Chicago during the fall?

During the fall in Chicago, it's advisable to wear layers; a cozy sweater for the daytime and a jacket for the cooler evenings, especially if you're visiting places like the Morton Arboretum or Lincoln Square Ravenswood Chamber of Commerce events.

MONTHLY POSTS

To learn more about what do to in specific months here in Chicago, click the links below:

• September  ( weather )
• October  ( weather )
• November ( weather )
• December ( weather )

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Private Tour Coordinator and Tour Guide

There is no shortage of things to discover in Chicago—I love being an urban explorer and uncovering its hidden places. I have an MA in Public History from Loyola University Chicago, and I have worked as a museum educator and kindergarten teacher. My desire to learn new things fuels my passion for educating others, which I get to experience every day as a Chicago tour guide. I live in the northern neighborhood of Rogers Park.

Whether you are a first-time visitor or a lifelong resident, the vibrant history and modern majesty of Chicago never ceases to amaze. I’m a graduate of Columbia College with an M.A. in Interdisciplinary Art. I’ve worked for many years as an educator at City Colleges of Chicago. As tour guide at Chicago Detours, I integrate my enthusiasm for culture and architecture with my passion as an educator. West Town/Noble Square area is home for me.

With our Chicago neighborhoods, vibrant cultural institutions and nearly two centuries of larger-than-life stories, there’s never a dull moment here! I’m a fifth generation Chicagoan and a graduate of Washington University in St. Louis. In addition to guiding tours, I’m a creative writer and amateur genealogist. I also enjoy the city’s dynamic theater scene. You can also read overlooked stories from 19th-century newspapers on my “Second Glance History” blog. I live in River North.

Chicago is unique as it always evolves into the future while holding on to the past. I’m fascinated by how people latch on to old architecture but happily pave over others. My background is in theater and performance and I’ve been a tour guide here for more than 10 years. Currently I’m finishing my Master’s in Public History at Loyola University because I love to teach the history of this scrappy city. I’m in the Edgewater neighborhood.

Operations Coordinator and Tour Guide

Chicago’s history is so fascinating, you could spend a lifetime uncovering its secrets…I’m willing to give it a try! I have an M.A. in US History from the University of Nevada-Las Vegas and then pursued doctoral studies in Urban History at the University of Illinois at Chicago. I love to learn new aspects of Chicago’s rich history and then share my knowledge as a tour guide with Chicago Detours. I live in Ravenswood.

Content Manager and Tour Guide

Chicago has so many neighborhoods, buildings, and by-ways that it’s hard to go long without seeing something new, or something familiar from a new angle. I studied Cinema History for my M.A. from the University of Chicago. I’ve worked as a culture writer for various publications and as an educator of the humanities at the City Colleges of Chicago. I’m thrilled to share my love of this city’s busy past and unique architectural spaces with Chicago Detours. I live in the Chicago neighborhood of Lincoln Park.

Amanda Scotese

Executive director and tour guide.