Top Chicago Walking Tours

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

(1,217)

4 hours 30 minutesFree Cancellation

from $101

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

(1,590)

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

(2,045)

3 hoursFree Cancellation

from $85

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

(149)

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

(15,998)

1 hour to 1 hour 30 minutesFree Cancellation

from $39

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

(459)

from $35

Chicago Walking Tour: Must-See Chicago

(143)

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.

from $35

Special Offer

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

(228)

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

$33

$44

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

(652)

3 hoursFree Cancellation

from $80

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

(38)

from $35

Chicago Architecture and True Crime Tour

(367)

1 hour 30 minutes to 1 hour 45 minutesFree Cancellation

from $35

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!

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

3.9

(2,233)

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

(423)

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

(9,889)

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.

from $45

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

(1,412)

Drink in a one-of-a-kind perspective on the Windy City when you go for an evening cruise, perfectly timed to coincide with the sunset. Hop aboard your open-top vessel (with an enclosed and climate-controlled lounge) in the heart of the Magnificent Mile, and cruise along the Chicago River. Then, see the skyline from a distance, and watch the skyscrapers light up, when you continue to Lake Michigan for a sunset viewing.

from $70

Lake Michigan Sunset Cruise in Chicago

4.5

(1,532)

Chicago Mobs and Haunts Walking Tour

from $45

4.7

(410)

1 hour 30 minutes to 2 hoursFree Cancellation

from $34

From deep-dish to hot dogs, taste Chicago Classic Dishes on our Chicago Food & Bike Tour. Ride by Bicycle, learn the stories, and savor every stop on the best Food & Bike Tour in Chicago.

Chicago dogs, deep-dish pizza, brownies, and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following your guide at a moderate pace through Chicago neighborhoods. On the day tour, ride through Wrigleyville, Old Town, Lincoln Park, and Gold Coast. On the night tour, visit Chicago’s Riverwalk, Millennium Park, Buckingham Fountain and the Lakefront Trail. As you go, stop for generous food and beer tasters.

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

(734)

4 hours 30 minutesFree Cancellation

from $89

Haunted Chicago Booze and Boos Ghost Walking Tour

(285)

2 hours 30 minutesFree Cancellation

from $36

Discover the heart of Chicago’s Chinatown with your authentic history and culture tours, exclusively offered by the official Chinatown Visitor Center. Led by experienced local guides, your tours dives deep into the neighborhood’s rich heritage, hidden landmarks, and cultural traditions. Unlike generic tours, we bring you behind the scenes with insider stories, community connections, and exclusive access to local favorites. Experience Chinatown through the eyes of those who know it best. A minimum of 2 participants is required for this experience. If the minimum is not met, the tour may be canceled, and you will receive a full refund.

2-Hour Chicago's Chinatown History and Culture Tour

3.8

(5)

from $30

Guide discussing A Sunday on La Grande Jatte

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

(490)

2 hours 30 minutesFree Cancellation

from $84

Take a deep dive into Chicago's food scene on a small-group walking tour. Head for several of the city's most-notable eateries, including Billy Goat Tavern, known for its "cheezborger," Pizzeria Uno, birthplace of Chicago’s legendary deep-dish pies; and Al’s Beef, a favorite since 1938. Along the way, hear about the friendly rivalry with New York's pizza scene, Chicago's meatpacking roots, 1920s speakeasies, gangsters, and more.

Chicago Food and Culture Walking Tour

4.6

(17)

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 $39

Chicago Walking Tour: The Magnificent Mile

(48)

Get to know the “must eats” in Chicago's buzzing Loop District on this small-group or private walking tour. As you explore, listen to in-depth commentary from your guide about the culinary history of Chicago, and get a taste of the city's most iconic foods, from hot dogs to deep-dish pizza. You'll enjoy personalized attention and the chance to chat about your favorite tastings, all while admiring Chicago landmarks along the way.

from $35

Chicago Food Tour: Taste the City’s Most Iconic Eats

4.8

(112)

Price varies by group size

from $87

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Top Attractions in Chicago

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What are people saying about Chicago

Chicago Architecture and True Crime Tour

Sue_S, May 2026

Best tour we’ve ever done!

We have done many Chicago tours, walking, on the train, bus, river boat, and this one was BY FAR the best one we’ve ever done. Our guide, David, was knowledgeable and professional. Learned so much about Chicago that I never knew! And I’ve done a lot of reading about the city over the years. Totally worth the time!!

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!

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

FELICE_W, Apr 2026

This was a wonderful,...

This was a wonderful, curated guided tour to the Art Museum by a native Chicagoan and art lover that provided an enjoyable and informative overview of all the Museum has to offer! It was also chock full of the history of the city! We highly recommend Joel!!

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 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.

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

Alison_P, Sept 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.