Top Chicago Walking Tours

Chicago in a Day: Food, History & Architecture Walking Tour

(1,208)

4 hours 30 minutesFree Cancellation

from $91

Price varies by group size

Discover the hidden gems of Chicago’s Loop area on a walking tour that showcases the best of the neighborhood’s stunning interiors and architectural must-sees. Step behind the facades to explore beautifully designed interiors—from art deco spaces to stained glass mosaics—as you follow a carefully curated route led by a guide. Along the way, learn about the city’s architecture, art, and history, and experience a side of Chicago often missed by travelers, all from a local’s perspective.

Original Chicago Architecture Interiors Tour: Dazzling Interiors

(1,582)

Eat your way through downtown Chicago on a walking food tour. Visit Millennium Park, the Palmer House Hotel, and other city landmarks and taste quintessential Chicago foods such as deep-dish pizza, hot dogs, and chocolate brownies. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels. A bike or kayak rental is also included in the tour cost.

from $35

Taste deep-dish pizza, a Chicago-style hot dog, Italian beef, Garrett’s popcorn & the original 1893 brownie on our top-rated Chicago Food Tours—the ultimate Chicago Culinary Tour experience!

Chicago Favorites Ultimate Food and Walking Tour

(2,042)

3 hoursFree Cancellation

from $85

Explore the hidden side of Downtown Chicago—and see sights that even many locals miss—on a small-group walking tour of the Pedway (an underground network of tunnels that connects Chicago buildings) and the vibrant Loop. Ideal for architecture fans, this tour includes insider stories and landmarks you wouldn't spot on your own—plus a chance to see Windy City icons like the Picasso Statue and Millennium Park.

Chicago Architecture Tour: Underground Pedway and the Loop

(457)

Admire some of the Windy City's most iconic views—and enjoy a time-saving, relaxing way to sightsee—aboard this pet-friendly Chicago River architecture boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including dozens of notable buildings, like the Wrigley Building and the John Hancock Building. In just one tour, you cover multiple branches of the Chicago River and learn insider facts and stories you'd otherwise miss.

from $35

Chicago Architecture River Cruise

4.8

(15,979)

1 hour to 1 hour 30 minutesFree Cancellation

from $39

Special Offer

This walking tour is a feast for the eyes, combining art, architecture, and history as you navigate through bustling downtown Chicago. In a small group, you’ll marvel at skyscrapers and mosaic murals as you discover stories and secrets about the city’s past. See the stunning interiors and exteriors of noteworthy buildings and leave with a comprehensive understanding of the city’s downtown.

Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour

(228)

Chicago Walking Tour: Must-See Chicago

from $35

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

(143)

Immerse yourself in one of Chicago's most vibrant neighborhoods—and head off the tourist trail to discover sights and bites many visitors miss—on this small-group Chinatown food and walking tour. With your guide in the lead, learn about the cuisine of different regions of China, and discover the history of Chicago's Chinatown. Along the way, enjoy a generous array of tastings, from dim sum to Sichuan cuisine and beyond.

from $35

A picture of Chicago Chinatown’s landscape shows vibrant streets, iconic arches, and rich culture—everything guests explore on our Chinatown Food Tours. Food Tours in Chinatown bring it all to life.

Chicago's Chinatown Food and Walking Tour

(648)

3 hoursFree Cancellation

from $80

Sample some of the Windy City's tastiest donuts—and head to locals-loved dessert destinations that most visitors miss—on this one-of-a-kind walking tour. With your guide in the lead, head to a number of Chicago’s tastiest donut bakeries, all while exploring the city's vibrant downtown Loop neighborhood. All tastings are included in the tour cost, and vegan, gluten-, and nut-free options are also available upon request.

Delicious Donuts & City Sights: Chicago's Original Donut Tour

(1,412)

Skip the hassle of planning your Chicago itinerary with this convenient hop-on hop-off tour, covering the city's must-see sights. With multiple strategically located stops, explore the Windy City at your own pace, hopping off to visit top attractions like the iconic Art Institute and famous skyscrapers. Enjoy insightful audio commentary as you cruise through the city, learning about its rich history and vibrant culture. Perfect for first-time visitors or those short on time, this tour offers flexibility and ease, ensuring you don’t miss any of Chicago’s highlights. Book your ticket today and experience the best of Chicago hassle-free!

from $70

Hop-On Hop-Off Sightseeing Tour by Open-top Bus

3.9

(2,232)

Get an insider's introduction to Chicago's most celebrated buildings during this architecture-focused walking tour of Michigan Avenue, State Street, and the vibrant Loop area. Revisit the heyday of the skyscraper and visit stunning, art deco-era interiors, from the Palmer House Hotel to the Chicago Cultural Center. Admission to the Chicago Architecture Center is included, with an introduction by the docent.

from $49

Chicago Walking Tour: Historic Treasures of Chicago

(421)

Discover the architectural gems of the Windy City from an ideal vantage point—and learn insider facts and stories about the city's top attractions—on this Chicago River cruise. Travel in comfort aboard a boat equipped with both indoor and outdoor seating areas. Covering more than 130 years of architectural history, this tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.

from $35

Chicago River 90-Minute Architecture Tour

4.7

(9,866)

Chicago Mobs and Haunts Walking Tour

from $45

4.7

(410)

1 hour 30 minutes to 2 hoursFree Cancellation

from $34

Chicago's Dark Side: Ghosts, Gangsters, and True Crime Tour

(38)

Learn all about the history beyond one of Chicago’s best-known thoroughfares—and spot numerous architectural icons as you go—on this small-group walking tour of the Magnificent Mile. Meet your guide at the Chicago Architecture Center and set off to soak up the street’s ambiance, and discover highlights like the Wrigley Building, John Hancock Center, and more. Entry to the Chicago Architecture Center is also included, so you can extend the experience.

from $35

Chicago Walking Tour: The Magnificent Mile

(47)

from $35

Chicago Architecture and True Crime Tour

(362)

1 hour 30 minutes to 1 hour 45 minutesFree Cancellation

from $35

Travel through architectural history on this express, small-group walking tour, which covers Chicago's most famous buildings in chronological order (and which is speedy enough to cater to the most time-pressed travelers). With a guide in the lead, there's no need to fuss over maps or worry about directions. Simply stroll along and listen to the in-depth commentary on Chicago's architectural history; you'll learn about each building, and will have plenty of chances to stop for photos.

Chicago Walking Tour: A Walk Through Time

(212)

from $35

Guide discussing A Sunday on La Grande Jatte

Skip-the-line: Art Institute of Chicago Guided Tour

(487)

2 hours 30 minutesFree Cancellation

from $84

The Art Institute of Chicago houses one of the finest American and Impressionist painting collections in the world, but it can be overwhelming to explore on your own. Remove the guesswork and maximize your time inside the museum on a private tour that covers major highlights by Picasso, Chagall, Warhol, Hopper, and others. Plus, there's no waiting to get inside, as the tour includes a skip-the-line ticket.

Private Art Institute of Chicago Skip-the-Line Guided Tour

(285)

2 hours 30 minutesFree Cancellation

from $90

Price varies by group size

Visit Cloud Gate on our Chicago Walking Tour—a Walking Tour of Chicago featuring Top Attractions, iconic art, and unforgettable Highlights at the city’s most photographed landmark.

This tour is ideal for first-time visitors or anyone eager to discover the city’s most iconic Top Attractions and Highlights on a guided Chicago Walking Tour. During this 2-hour Walking Tour of Chicago, stroll through downtown’s beautiful streets as expert local guides share rich history, colorful characters, and insider tips to enhance your list of Things to do in Chicago. Your experience includes a FREE 2-hour bike or kayak rental—bike the Lakefront Trail or kayak on Lake Michigan for unforgettable skyline views. Bobby’s Bike Hike tours are nationally recognized by National Geographic, USA Today, and Condé Nast Traveler for excellence in storytelling and urban exploration. You’ll see the landmarks that define Chicago: Millennium Park, the Chicago Riverwalk, the Wrigley Building, the Chicago Theatre, and the famed Magnificent Mile. Covering 1.5 miles (2.25 km) of easy, flat terrain, this tour offers a complete and memorable introduction to the city.

Chicago Walking Tour of Highlights with Free Bike or Kayak Rental

(5)

Admire the ornamental facades and intricate interiors of the Windy City's art deco buildings during this in-depth walking tour of the vibrant Loop. This small-group tour will introduce you to some of the city's highlight architectural landmarks and its rich history, all in a single excursion. As you go, get an up-close look at landmarks that many other tours overlook—and learn insider stories from your architecture-expert guide.

from $45

Chicago Walking Tour: Art Deco Skyscrapers Loop

4.8

(178)

from $35

Chicago Murder Mystery Tour

(734)

Enjoy a quintessential Chicago experience—and see more of the city's highlights in less time—on an architecture-themed boat tour of the Chicago River. Pick from multiple convenient start times, and board your vessel directly from the Chicago Riverwalk. Thanks to your trained docent guide, receive a rich introduction to the Windy City’s history, key landmarks, and architectural highlights—and spy landmarks like the Marina City towers and Navy Pier from the water’s edge.

from $35

Chicago Architecture Center River Cruise aboard First Lady

(5,723)

1 hour 30 minutes

from $57

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Chicago Architecture Tour: Underground Pedway and the Loop

Marcellus_C, Apr 2026

Excellent tour with a lot of learning!

This was an excellent activity that gave us a history of the underground walkway, in addition to some of the historical buildings in Chicago. Henry was very knowledgeable--he was able to answer 95% of our questions (some of our questions did come out of left field!). Keep in mind - the tour starts across the street from City Hall and ends elsewhere. It wasn't a strenuous walk at all (one of us had knee issues--he didn't complain at all.) About the only "climbing" we did was on stairs exiting the underground pedway. Henry also gave us plenty of opportunities for bathroom breaks. My only regret was not eating a good breakfast before taking the 2+ hour walk. (P.s. Henry was an excellent guide for this because of his background in architectural/structural engineering.). I would take this tour again!

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

Carol_C, Apr 2026

What are you waiting for? BOOK This TOUR!!

We had a great time! My son (17) and I are true crime and ghost junkies and Andre’s tour did not disappoint. He is an amazing storyteller and guide. Great information along with a true insight to the city. Walking was the way to go. We both would highly recommend the tour. 90 min, easy walking and it flew by all ages would enjoy. Why are you still reading this review… you should be booking your tour!🤩

Chicago Architecture and True Crime Tour

Kimberly_C, Apr 2026

Fantastic tour with David!

This was such a fun and delightful tour with David! He is a great storyteller. His insight and passion for Chicago architecture and crime lore stayed with us long after the tour was over. The 90 minutes flew by though we were fortunate to have good weather. There were many stops along the way that brought us inside some remarkable spaces. Overall, we highly recommend David and this tour experience! 10 out of 10!

Chicago's Chinatown Food and Walking Tour

Tessa_S, Apr 2026

Great food tour

Lots of delicious food and history about Chinatown in between to give our stomachs some time to settle. It's the perfect amount of food where you don't feel like you're wasting a ton but definitely won't leave hungry. Loved it, thank you for having us!

Chicago Mobs and Haunts Walking Tour

Lynn_H, Apr 2026

Lark's Knowledgeable and Entertaining Tour

Lark was a fantastic tour guide- knowledgeable, enthusiastic, and genuinely engaging. Our group was small, which made the experience feel personal and easy to connect with. We were able to ask plenty of questions, and Lark handled each one with ease and insight. His depth of knowledge about Chicago's history was especially impressive. He shared fascinating stories and facts that we never would have discovered on our own. The places we visited were rich with historical significance, and his storytelling made each stop come alive. We absolutely recommend Lark to anyone looking for a fun and informative tour of the city.

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Cristina_M, Mar 2026

Great tour to learn about Chicago in less than 2h!

The tour was great! We were in Chicago less than 2 days as my colleague and I were coming back from work meetings in other state and we didn't have a lot of time to explore the city on our own. We learn a lot from Spencer (our guide) not only about interiors but also about the history and culture of the city. He also pointed out scenes from famous movies which make it fun! He made us very cool photos and Also he recommended us a few places to have a proper Chicago lunch 😋 and also send us after other recommendations to do. Really enjoyed our time in the city and obviously the tour! Thank you Spencer! 😉

Delicious Donuts & City Sights: Chicago's Original Donut Tour

Lindsey_S, Mar 2026

Donut miss this tour!!!

This was such a fun morning! Nick was engaging, funny and knowledgeable about the shops we visited and sites of downtown. We got to see several new parts of Chicago we hadn't seen yet, and sample some absolutely delicious donuts until we were completely stuffed - you won't go hungry on this tour and we even took some leftovers for the road! Thanks for making our last morning in Chicago GREAT!

Chicago City Minibus Tour

Lindsey, Mar 2026

Sit back, relax and enjoy the show!

Another group cancelled due to transportation issues, so we lucked out having a private tour with Rick! Rick was thoughtful to ask what we had already seen/done in Chicago and was so kind to modify the original itinerary to show us some different parts of town we hadn't been to yet. The tour was a great mix of sightseeing, informative facts and humor. He gave us some appreciated recommendations for food and other stops. It can be hard to take everything in when walking around town since so much of your attention must be focused on uneven terrain, traffic, other pedestrians, etc. This was awesome to be able to sit back, relax and enjoy the show. Highly recommend!

Chicago Loop District Food Tour with Deep Dish & Beef Sandwich

Sabrina_C, Oct 2025

Excellent

Michael was our tour guide and he was excellent. He even helped us find parking on the street .The tour starts with a short visit inside the library which was the meeting spot. He had lots of stories to tell, and he was very entertaining. He was also very knowledgeable about Chicago. I expected sample servings of all the food, but we actually had an entire slice of pizza, a half of a beef sandwich, an entire hotdog, an entire churro, an entire brownie, and a small sample bag of popcorn. The tour took exactly 3 hours as advertised. I recommend this tour and hopefully you have Michael as your tour guide.

Chicago Sightseeing River and Lake Cruise

Erica_S, Sep 2025

Great experience but hard to find

The tour was great with a very knowledgeable narrator. I enjoyed it. However, we missed out scheduled tour because. Of the difficulty in finding the location. We had to call and a wonderful agent stayed on the phone with us gave us directions and told us where to park. Patrons should be given more information on the location.

Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults

Alison_P, Sep 2025

Bike tour around Chicago

I had an afternoon to myself and live the outdoors so I booked the 4 hr bike, bites, and brews tour. I had a great time and was completely comfortable doing this tour by self as the guide was great and others in the group very friendly. Not overly strenuous at all, just a decent ride with plenty of stops to learn about Chicago.