Top Chicago Walking Tours

Chicago Walking Tour: Art Deco Skyscrapers Loop

Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.

Chicago River 45-Minute Architecture Tour from Magnificent Mile

45 minutesFree Cancellation

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.

Chicago River 90 Minute Architecture Tour

Take in sweeping views of Chicago from the air during a scenic helicopter flight that offers a premier experience of the Windy City. This private 45-minute flight provides an aerial look at landmarks such as Millennium Park, Navy Park, and Wrigley Field. Ideal for a special occasion, this helicopter tour accommodates up to three people and includes the use of noise-cancelling headsets to hear the pilot clearly.

Private 45-Minute Chicago Skyline Helicopter Tour

45 minutesFree Cancellation

Chicago Explorer Pass: 35+ Things To Do - Includes 360 CHICAGO

1 to 30 days

4.0

(370)

from $84

On this small-group Windy City bike tour, you won't just pedal past the lakefront neighborhoods of Chicago's North Side—you'll see more of the city than you could if exploring on your own. Follow a local guide along quiet streets, city parks, and scenic beaches, starting at Lake Shore Drive and continuing along Rush Street and the Magnificent Mile. As you go, glimpse offbeat attractions like the Playboy Mansion, Oprah’s penthouse, and the Victorian houses of Old Town.

Smiles ear to ear as you ride our Chicago Bike Tour through scenic Lakefront Neighborhoods. Fresh air, open paths, and lake views make this the ultimate Bicycle Tour in Chicago.

Bike Tour of Chicago's Lakefront Neighborhoods

3 hoursFree Cancellation

Outside of Italy, few places in the world are as famous for their pizza as Chicago. Eat like a local as you travel off the beaten path to savor the city's best pizza, traveling by bus so you can cover more food hot spots in less time. Discover the science behind ingredient selection and baking as you sample slices from historic pizzerias, and take away plenty of tips to enhance your eating in Chicago.

3 hours 30 minutesFree Cancellation

Chicago Pizza Tour

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

Delve into the rich history and notable architecture of one of Chicago’s most luxurious neighborhoods—and learn insider stories as you go—with this self-led smartphone audio walking tour. Upon booking, download the app and set off at a time and pace that works best for you. Discover Gold Coast landmarks from historic piano bars to the original Playboy Mansion, and stop and start the tour whenever you like.

Chicago's Gold Coast Hidden History: A Self-Guided Audio Tour

50 minutesFree Cancellation

Discover a side of the Windy City that many visitors overlook—and immerse yourself in its vibrant street art scene—on this urban walking tour. With your art-expert guide in the lead, you can focus on soaking up the city's ambiance, and spotting artworks and murals you may not have discovered on your own. As you go, listen to in-depth commentary about the artists and artworks, and explore some of the city's hippest neighborhoods.

Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals

Dive into this captivating journey through the hallowed grounds of Chicago’s Graceland Cemetery. As we stroll amidst the stunning and serene beauty of historic resting places, you'll encounter the final resting spots of architectural visionaries like William LeBaron Jenney, John Root, Louis Sullivan, Mies Van der Rohe, and Daniel Burnham. This unique walking tour not only unveils the grandeur of tombs and mausoleums but also shares the stories of Chicago's celebrated architects, whose creativity shaped the city's skyline. But our journey extends beyond the architects' realm, as we also discover the final resting places of other notable figures with deep pockets—pioneers of industry such as Marshall Field, Palmer Potter, George Pullman, Walter Newberry, and more. Their legacies, intertwined with the fabric of Chicago's history, add an extra layer of richness to this immersive tour.

The Deep Pockets Of Graceland Cemetery Walking Tour

Get the most out of your trip to Chicago as you enjoy discount access to five of the city’s top attractions with the CityPASS®. This easy-to-use mobile ticket grants you free entry into top-tier sights including the Chicago's most famous aquarium and Skydeck Chicago, plus your choice of admission to three of the following attractions: Field Museum, Art Institute of Chicago, Museum of Science and Industry, 360 CHICAGO Observation Deck, Adler Planetarium, or Shoreline Sightseeing Architecture River Tour.

from $144

Discover one of Chicago’s most picturesque, historic neighborhoods—and learn all about the buildings that make it an architectural standout—on this small-group walking tour of Wicker Park. Meet your guide in the morning, and set off on foot: you’ll discover the 19th-century workers’ cottages that fill the neighborhood, will admire local landmarks like mansions and historic baths, and will learn all about the city’s architectural history.

Historic Homes and Cottages of Wicker Park Walking Tour

Historic Homes and Cottages of Wicker Park Walking Tour

Step into the heart of Chicago with this in-depth, small-group walking tour of the Loop neighborhood, the heart of the Windy City's downtown. Stop to check out the elevated “L” train, admire historic buildings, discover lesser-known corners of this vibrant area, and view its best-known public artworks, too. You’ll come away with a deeper sense of Chicago’s rich history and architecture.

Chicago Loop Walking Tour

Chicago is renowned for its dynamic dining scene—and this private walking tour offers a personalized introduction to its must-eats. Pick a time that works best for you, and head to Gino’s East: one of the city’s classic deep-dish pizzerias. From there, set off on a tour of the Loop, where you’ll taste sweet and savory treats—and learn about the city’s architecture, history, and culture as you go.

Private Chicago Food Tour with Deep Dish and Beef Sandwich

3 hoursFree Cancellation

Price varies by group size

Discover the Art Institute in a unique way that blends art, storytelling, and photography. After a warm welcome, we'll head inside with tickets included & begin an immersive journey through the galleries. Together, we'll explore the museum's most celebrated highlights, featuring masterpieces by Monet, Picasso, Van Gogh, Dalí, Warhol, Hopper, and more. I'll share fascinating stories that bring the art and its creators to life, revealing the hidden meanings and personal histories behind. Along the way, I'll capture beautiful, candid photographs at the best photo spots. Using your phone or my iPhone 14 Pro, I'll guide you with simple posing tips and angles to ensure you receive stunning, professional-quality images perfect for memories or social media. Anyone looking for more than just a museum visit, you'll leave with gallery-worthy images plus knowledge that transforms how you experience art—an unforgettable blend of photography, storytelling, & culture. Looking forward to hosting you!

The Art Institute in Chicago Highlights Tour & Photoshoot

The Art Institute in Chicago Highlights Tour & Photoshoot

1 hour 15 minutesFree Cancellation

Explore the Loop's famous architecture—and learn insider facts and stories that you wouldn't encounter if exploring alone—on this small-group walking tour. Led by your Chicago Architecture Center–certified guide, you'll discover some of the city's oldest skyscrapers, dating from the late 19th and early 20th centuries. Admire the Rookery building, see the Marquette building, and much more, all while soaking up the city's ineffable energy.

Chicago Walking Tour: Historic Skyscrapers

Chicago’s “L,” or elevated train, is an icon of public transportation and a major feature of the Loop neighborhood. On this interactive tour, you’ll learn about the railway’s history while experiencing it as a rider. Meet your guide in the morning and set off with just a small group for company. As you ride between stops, you’ll also view Chicago icons like the Willis Tower, and will learn about the city’s architectural history.

Chicago City Tour: Elevated Architecture Tour with Train Ticket Included

Chicago is world-renowned for its architecture—and this small-group walking tour offers the ideal introduction to its iconic buildings, its architectural eras, and the starchitects who have left their impression on the city. Meet your guide at the Chicago Architecture Center and set off on foot: you’ll discover highlights like the Wrigley Building and Marina City, will see works by Renzo Piano and Frank Gehry, and will learn all about Chicago history.

Chicago Walking Tour: Connecting Past and Present

1 hour 45 minutesFree Cancellation

Considered Chicago’s original “Millionaire’s Row,” Prairie Avenue in the Near South Side is renowned for its Gilded Age mansions—and this tour makes exploring easy (and delightfully spooky). In the evening, meet your guide in front of the Glessner House, and set off with ghost-hunting gear to accompany you. In between spotting highlights including the Marshall Field Jr. Mansion and the Henry B. Clarke House, you’ll hunt for specters and hear ghost stories.

Prairie Avenue Haunted History Tour and Ghost Hunt

Capture the highlights of your Windy City visit—and walk away with professionally taken portraits—on this private photo shoot experience. Meet your guide at a time and place that work best for you; you can also select your preferred duration and number of photos. Then, get ready to strike a pose: your guide will take a number of photos, and chronicle your special moments. See Windy City highlights as you go

Professional Photo Shoot in Chicago

4 hoursFree Cancellation

Price varies by group size

There’s so much amazing architecture in Chicago but wandering around alone can leave you overwhelmed, and unsure of what you’re looking at. Check out some of Chicago's most important new buildings on an architecture walking tour. The tour is focused on the area around the Chicago Architecture Center (CAC), beside the Chicago River, so you don’t get overwhelmed exploring the whole city. Admission to the CAC’s galleries is also included.

Chicago Architecture Walking Tour: What's New

Chicago Architecture Walking Tour: What's New

Learn why Chicago has such a notable wealth of architectural highlights—and discover many of them up close and personal—on this introductory, small-group walking tour. Led by your architecture-expert guide, set off on foot to discover landmarks from the Wrigley Building and Marina City Towers to Daley Center and the Chicago Theatre. Along the way, learn insights and stories you’d miss if exploring the city solo.

Intro to Chicago Architecture

1 hour 45 minutesFree Cancellation

Head to one of Chicago’s top neighborhoods for food lovers—and try donuts from four of the Windy City’s top specialty bakeries—on this indulgent walking tour. Meet your guide at the Chicago French Market in the morning, and come hungry: you’ll enjoy four different donuts, each representing different culinary styles and traditions. As you go, wander the West Loop and Restaurant Row, and learn more about Chicago’s dining scene.

Chicago West Loop Sweet Treats Food Tour: Donuts, Cookies, & More

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

...

3 4 5

...

Must-Dos in Chicago

1 / 2

What are people saying about Chicago

Todd_M, Nov 2026

Excellent Experience!

Sydney, an incredibly knowledgeable and friendly guide, led us on a fantastic walking tour of The Loop. The tour delves into the city’s rich history, infamous criminals, and even shares a few chilling ghost stories. It’s a great way to get some exercise while immersing yourself in Chicago’s past.

Chicago Gangsters and Ghosts Walking Tour

Avery_W, Oct 2026

Do iiiiiit

This experience was probably one of the best parts of our trip. We were so surprised. Tanner was really engaging with his story telling, he made you want to keep listening and learn about the history of Chicago. I would highly recommend this to anyone that loves history and/or Chicago. We really loved our experience. Give Tanner a raise!!!!!!

Original Chicago Architecture Interiors Tour: Dazzling Interiors

clint_w, Oct 2026

Great Tour

Henry was our tour guide and he truly did an amazing job! We started at the Chicago board of trade and went to about 5 buildings. He was so knowledgeable and the added experience he has of being an architect makes it so much better. You can truly see his passion for the subject and he appreciates it so much. If you really want to learn the why behind design elements of some of the most iconic buildings in Chicago go on this tour!

Chicago's Chinatown Food and Walking Tour

Lucy_G, Oct 2026

Best food tour in Chicago

Great way to learn about Chinese food, meet people, and have a great, delicious meal. We had Cantonise dumplings and noodles, Szechuan chicken and rice, lamb sandwich from Xian, and we finish with a custard pastry. All the food was delicious. Highly recommended.

Lake Michigan Sunset Cruise in Chicago

michelle_m, Oct 2026

Solo Vacation Week -KCMO Visitor

I have always wanted to have a fun adventure. My bucket list of my things to do includes riding the Subway Train, Boat Ride on Lake Michigan as the Sun sets and be Solo. It's been a challenging year for me. I lost a family member, a personal friend and a professional colleague of mine. This is my way of honoring my friends and family and celebrating them.

Chicago Architecture Tour: Underground Pedway and the Loop

baldy44, Oct 2026

Even though I worked in...

Even though I worked in the Loop for 10 yrs, I hadn't used the pedway. Guide Colleen was fun, knowledgeable, personable, and taught us interesting bits of Chicago history never heard before. She also created a nice connection among our small 6-person tour (people who didn't know each other before the tour).

Bike Tour of Chicago's Lakefront Neighborhoods

Willem_B, Sep 2026

Great afternoon!!!

We had a great bike ride with Kevin our guide. He showed and told a lot about Chicago. His enthusiasm was contagious. With our club of European diversity, he made a connecting group. We really enjoyed this afternoon. This is really recommended!!! And nice bikes!!! Kevin, thanks again 🚴🚴‍♀️🚴‍♂️🚴🚴‍♀️🚴‍♂️ warm regards, from Willem and Roos, the Netherlands

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

Jan_B, Sep 2026

Great intro to the food and history of Chicago

This was an easy biking 3 1/2 hour tour for the evening tour. Just a note the tour does go rain or shine, and we definitely got caught in the rain towards the end! Our guide, Nora, was a native of Chicago and gave us lots of fascinating history of both food and the city.

Chicago Architecture and True Crime: Halloween Edition

Arite_M, Sep 2026

Entertaining, easy to follow – highly recommended!

David made our Chicago Crime & Architecture Tour a real highlight. You can tell he has comedy genes: he presents even complex topics in an incredibly entertaining, engaging, and easy-to-follow way. Although we’re not native English speakers, we could understand him perfectly and truly enjoy the tour. His mix of humor, knowledge, and storytelling turns this into much more than a standard guided tour. Highly recommended for anyone who wants to experience Chicago in a unique and memorable way!

Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich

Candace_W, Aug 2026

Just do it!

My family and I did this tour while we were in Chicago this past weekend and we were very happy with our experience. Sue was our guide and she was a wealth of knowledge. You could really tell that she enjoys her job. Before we got started, she made sure that everyone in our group was accounted for and even went out of her way to ensure that a few unintentional latecomers were able to jump in without disruption. She was well-prepared with anything we would've needed like wet wipes, hand sanitizer and even a Tide pen! All of the food options were amazing, with the Lou Malnati's pizza being my favorite dish. I would 100% recommend this tour to anyone visiting Chicago! You'll feel like a local for a few hours. :)

Private 45-Minute Chicago Skyline Helicopter Tour

Richard_W, Aug 2026

Our Family day in the sky...

Our Family day in the sky was absolutely perfect! There were a few nerves when we arrived but pilot answered all of our questions and guide us on an unforgettable tour, circling downtown, Navy pier, the Stadiums, Chicago River - it was incredible. If you are thinking about it, just do it! It’ll be a memory that will last a lifetime.

Chicago Night Crimes Tour by Bus

Nicolette_R, Jun 2026

Best use of time, No Regrets!

The tour was amazing! I was happy to be driven around downtown area and learn of the various neighborhoods, in addition to the crime history. The tour guide and driver were wonderful! No comments or recommendations, very happy tourist! Can’t wait to come back and bring more riders! See you soon Chicago Crime Tours!