Top Chicago Walking Tours - page 5

Haunted Chicago Exploration Game and Tour

4.0

(6)

Free Cancellation
2 hours

from

The Art Institute of Chicago is home to over 300,000 works of art by local and international artists. With so much to explore, it’s easy to get overwhelmed by all of the options during a visit. Sit back and let an expert guide handle the planning as they take you through the museum’s major pieces. Learn about the history and context behind each piece in this culturally enriching experience.

Art Institute of Chicago Private Expert Guided Tour

(89)

Free Cancellation
2 hours

from $215

What do the artists Picasso, Chagall, Miro, and Kapoor all have in common? Incredible public art hiding in plain sight amidst world famous architecture. This 2.5 hour small group (12 Guest Maximum) guided walking tour is perfect for busy sidewalks and getting up close to monumental art! Highlights Include: Edward Kemeys’s “Lions” Juame Plensa’s “Crown Fountain” Anish Kapoor’s “Cloud Gate” (The Bean) Eduardo Kobra’s “Muddy Waters” Pablo Picasso’s “Untitled” Joan Miro’s “Chicago” Alexander Calder’s “Flamingo” Marc Chagall’s “Four Seasons” Louis Comfort Tiffany Art Glass Creation Augustus St. Gaudens “Abraham Lincoln” Marcel Francois Loyau “Clarence Buckingham Fountain”

Downtown Chicago Guided Walking Tour Semi-Private 12ppl Max

(1)

Free Cancellation
2 hours 30 minutes

from $52

Discover the heart of Chicago’s architectural legacy on this guided walking tour through the historic Loop District. Step back in time as you explore some of the world’s first skyscrapers and venture inside a collection of the city’s most influential and iconic buildings. Your expert local guide will share captivating stories about the rise of Chicago, the Great Fire, and the visionary architects whose bold designs shaped the skyline we know today. This tour offers the perfect mix of history, design, and city energy—a must for architecture lovers and curious travelers alike. - Explore the birthplace of the modern skyscraper - Step inside landmark buildings like The Rookery and the Palmer House - Learn about the Great Chicago Fire and its lasting impact on the city - Enjoy a relaxed pace through Chicago’s vibrant downtown Loop

Private Chicago Architecture Walking Tour

4.8

(6)

Free Cancellation
3 hours

from $211

️ Chicago Instagram Walking Tour (Private & All- Inclusive)

Free Cancellation
4 hours

from $236

4.3

(6)

Private Frida and Friends Tour in Pilsen

Free Cancellation
2 hours

from $240

Per group

Make your Chicago trip unforgettable with a private photoshoot at the city’s most iconic locations. Your photographer customizes the route for your style and occasion—capture candid portraits by the Bean, Riverwalk, Wrigley Building, Millennium Park, and more. Solo adventurer, family, couple, or group—everyone’s welcomed! Choose a 30-minute or 1-hour shoot and receive 20–45 high-res, professionally edited photos delivered via a private online gallery within five days. Enjoy insider tips and authentic, natural photography from a top-rated team.

Private Vacation Photoshoot with Photographer in Chicago

3.7

(3)

Free Cancellation
1 hour

from $152

Channel your inner detective on this immersive, self-guided scavenger hunt through Chicago’s Loop! Step back to 1923 as you gather clues, solve a murder mystery, and unlock secrets of Prohibition-era Chicago. Your group receives a mystery kit, then follows a story-driven trail at your own pace—no app required. Observe real landmarks and hidden clues as you work together, making this ideal for friends, families, and groups seeking a hands-on, flexible adventure. The perfect blend of history, teamwork, and local intrigue in the heart of Chicago.

Chicago Mystery Scavenger Hunt: Solve the Loop’s 1920s Whodunit

(1)

Free Cancellation
1 hour

from $23

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

3.5

(4)

Free Cancellation
2 hours

from $30

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

4.4

(8)

Free Cancellation
4 hours

from $206

This self-guided walking tour is perfect for last-minute travelers who love chocolate! Travelers will use the eATLAS app for directions on where to go, and what to do--map included. You can start and pause the Adventure whenever it is convenient for you. Chicago was once the “Candy Capital of the World,” and chocolate has been a rich, decadent part of the city’s culinary history longer than deep-dish pizza and Italian beef. Milton Hershey even learned how to make chocolate in Chicago at the 1893 World’s Fair. Some of the world’s most beloved chocolate treats, including Tootsie Rolls, Baby Ruth, Butterfinger, Snickers, 3 Musketeers and Milky Way, were invented or are manufactured here. There are 8 delicious Loop and River North stops on our tour/scavenger hunt. Simply read the clues and follow the directions to guess the answers. Hints are provided if you need help. You won’t be required to buy anything, but if you need a quick pick-me-up, what’s better than chocolate?

With this AI app, you're no longer restricted to crowded group tours or rigid scripts. Explore iconic Chicago sites like Millennium Park and the Magnificent Mile—or dive deep into 1920s mobster hangouts and hidden Prairie Style masterpieces. Ask about literally anything that catches your eye—from a Gilded Age historic district to a secret jazz club or a towering steel-and-glass skyscraper. The Windy City's deepest secrets are entirely yours to uncover. Point & Discover: Snap a photo of any monument or museum masterpiece to instantly receive a captivating and accurate story. It’s like having a historian in your pocket! Ultimate Freedom: Navigate seamlessly with interactive map-based audio tours. Your schedule, your pace, your rules. Choose Your Vibe: Select a narrator persona that matches your style—from a deep-diving scholar to a fun companion for the kids. Get Started: 7 Days of Premium Access available instantly for iPhone and Android.

3.4

(5)

Chicago Chocolate Tour

Free Cancellation
2 hours

from $8

Chicago and All MidWest Self Guided AI Audio Tours for 7 Days

Free Cancellation
7 days

from $12

Special Offer

Roam the lively heart of Lincoln Square with its cafés, delis, and other fun and fascinating stores; stand beside the Berlin Wall; take in ghastly history, gorgeous murals, and 300-year-old oak trees; and, at your journey’s end, find yourself rewarded by the sight of an architectural gem. As you solve challenges, the story unfolds and exact directions on your phone will guide you to the next location. Join the game! Highlights include: • Explore Merz Apothecary, Gene's Sausage Shop and Delicatessen, Lincoln Square Mural and lesser-known places. • Enjoy a uniquely crafted story brought to you by our top-notch/gifted/talented writers. • Try a new type of experience, the perfect mix between a tour, outdoor escape game, and treasure hunt. After your booking you will receive an email with instructions on how to download and play the game on your phone. We recommend that each user purchases a ticket for an optimal experience, although several people can share a phone.

4.5

Secrets of Lincoln Square: Self-Guided Puzzle Quest in Chicago

Free Cancellation
1 hour 50 minutes to 2 hours 20 minutes

from

Discover the rich history and architecture of downtown Chicago with local expert Dave Lineal. Walking underneath the soaring buildings, we will learn how Chicago grew to become a global force in culture, commerce, and architecture. How did this roaring city come to be? We will hear the tales of Chicago history immersed in the places where it happened -- exploring historic building interiors like the world's oldest skyscrapers, City Hall, and the old library. This deep dive in city history and architecture aims to deepen our appreciation of what Chicago is today.

History and Architecture of Chicago Loop Walking Tour

(13)

Free Cancellation
2 hours

from $30

Explore the new Old Post Office Building, whose early 20th-century design has been adaptively reused into a beautiful, modern Class A Office building. It once seemed as though the stunning architectural details of Chicago's Old Post Office would be lost to time while the building sat vacant for almost two decades. But the 2.8 million square foot building, completed in 1934, recently went through a monumental renovation and now serves as a modern multi-use event and office space that meets today's need for large, light-filled workspaces. See how historic artifacts and building details have been creatively incorporated into the Old Post Office's design including the conversion of the roof to a 3.5-acre urban rooftop park. Old places can become new spaces when a developer with vision collaborates with an award-winning architectural team.

Explore the Historic Old Post Office in Chicago

4.9

(16)

Free Cancellation
1 hour 30 minutes

from $15

Chicago Haunts and Hooligans Tour

(37)

Free Cancellation
1 hour 30 minutes

from $35

For sightseers looking to put a spooky spin on their night and avoid the overpacked city tours that tell history most of us already know, this Chicago Family-Friendly Ghost Tour is just the thing. Stop at popular Chicago attractions, including the Flying Dragon sculpture, the Chicago Stock Exchange Arch, the Abraham Lincoln statue, and Buckingham Fountain, while a guide tells you ghost stories along the way.

Ghosts of Chicago Family Friendly Ghost Tour

4.1

(12)

Free Cancellation
1 hour 30 minutes

from $30

Discover the vibrant Wicker Park neighborhood as you stroll from the Polish Triangle through the Milwaukee Avenue shopping and dining district. This guided walking tour circles Wicker Park, showcasing stunning Victorian mansions on Beer Baron's Row while sharing engaging trivia about the area’s rich ethnic and commercial history. Enjoy insights into the local arts and entertainment scene and uncover the best spots to eat and drink along the way. Test your knowledge with trivia, and compete for a special prize at the end of the tour. - Explore the historic Wicker Park neighborhood on foot - Visit iconic locations like the Polish Triangle and Beer Baron’s Row - Engage in neighborhood trivia for a chance to win a prize - Learn about the area's ethnic history, arts scene, and dining hotspots

Wicker Park Walking Tour History Trivia and Local Flavors

(1)

Free Cancellation
1 hour 30 minutes to 2 hours

from $40

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

4.8

(9)

1 hour 30 minutes

from $45

This is the first tour in Chicago that truly celebrates Chicago's street art scene. No other tour takes guests out into the streets to showcase and highlight the vibrant street art scene, which many people overlook on a daily basis. As we walk along the Union Pacific viaduct, you’ll learn the history of this 50-year-old project and watch it evolve from a community-based mural program to an international attraction featuring artists from all over the world. You’ll deepen your understanding of the elements of street art by exploring the eclectic work of hundreds of artists and volunteers. We hope you join us to experience something truly unique in Chicago.

3.0

Offbeat Fulton Market Graffiti and Murals Street Art Tour

Free Cancellation
2 hours

from $40

A Chicago hot dog loaded with bold, colorful toppings is one of the tastiest Things to do in Chicago. Our Chicago Food Tours feature this classic bite, making Food Tours in Chicago unforgettable.

Get ready for the most complete adventure the city has to offer—an immersive Full Day Chicago Food Tour and Walking Tour that blends Chicago’s legendary flavors with its most iconic landmarks. Savor Chicago Pizza, Hot Dogs, Italian Beef, Garrett’s Chicago Mix Popcorn, and the original Palmer House Brownie, or elevate your day with our VIP craft beer upgrade. This unforgettable Chicago in a Day Tour explores Millennium Park, the Chicago Riverwalk, Michigan Avenue, Cloud Gate, Chicago Theater, and more, guided by true local experts. Enjoy a 5-hour journey through culture and cuisine, plus a FREE 2-hour bike or kayak rental to continue the adventure along Lake Michigan. Recently honored among the “Top 10 Food Tours in America” (USA Today) and “Top 20 Food Tours in the World” (TripAdvisor), this award-winning Culinary Tour is one of the top Things to do in Chicago. Don’t miss the most delicious, scenic Full Day Food Tour in Chicago—all in one extraordinary day.

Chicago Full-Day Walking Food Tour with Free Bike or Kayak Rental

Free Cancellation
5 hours

from $99

See Chicago through the eyes of Al Capone and the Everleigh Sisters at your own pace with this affordable walking tour. • Walk in the footsteps of the gangsters, bootleggers, hoodlums, gunmen, and crooked cops and politicians who made up what was known as the “Chicago Outfit” • Hear from producer Richard Junger, an urban historian, professor and author passionate about Chicago • Do it all in 45 minutes or linger at stops along the way with complete control over when you start and finish • Get unlimited use before your booking date and after it • Use the virtual tour option at home Once you’ve booked, you’ll receive a ticket with instructions and a unique code listed under “Before You Go”. Then simply install the VoiceMap app and enter your code. The app displays directions to the starting point, and when you’re in the right place, just pop in your headphones and tap start. VoiceMap has automatic GPS playback, with turn-by-turn directions. It also works offline.

Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour

45 minutes to 1 hour

from $10

Explore the surprising beauty and history of the Windy City with this combo tour of Chicago’s Millennium Park and Riverwalk! Snap a picture by the famous Cloud Gate sculpture and get away from the hustle and bustle in the city’s most iconic park. Then, stroll along the picturesque riverside, admire Chicago’s totally unique architecture, and learn the fascinating stories behind the city’s skyline. This combo is the easiest, best way to get to know this complex city! After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want. This isn't an entrance ticket. Check opening hours before your visit.

Chicago Riverwalk & Millennium Park Self-Guided Audio Tour Bundle

Free Cancellation
1 to 2 hours

from $25

Skip the crowds this is a private tour for your group only! How about an unforgettable time in Chicago with your beloved? If you're looking to have the most romantic time while visiting famous attractions of Chicago, then you can't miss this walking tour! Why is Chicago called "The Windy City"? Did you know that Chicagoans call The Cloud Gate "The Bean"? Do you know why? Together with the professional tour guide you will discover so many different facts about Chicago and you will hear the most romantic stories as you walk along the beautiful and historical streets of Chicago. Fill your hearts and memories with the most beautiful views and photos of The Windy City!

Romantic Chicago Walking Tour: Love Stories & Landmarks

Free Cancellation
2 hours

from $652

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

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Top Attractions in Chicago

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What are people saying about Chicago

Rebecca_M, Mar 2026

Art Tour Extraordinaire

This was a tour about which songs will be song! Our guide, Spiro, was AMAZING! He was knowledgeable, patient, kind, and engaging…he even extended the tour slightly to make sure we all got to see what we wanted to see within the museum (for me, that was St. George Slaying the Dragon, which was not part of the tour). I love tours, and I have taken them all over the world, and this one ranks amongst the best!

Chicago Architecture and True Crime Tour

Leslie_W, Mar 2026

A Little Something for Everyone

This tour is as the perfect mix of architecture, history, true crime, and pop culture for us—a little something for everyone. We loved that most of the stops were indoors so we could hear our guide well and dip out of the blustery cold for a bit each time.

Chicago Architecture Tour: Underground Pedway and the Loop

Julienne_T, Mar 2026

Pedway Tour

Heath was our tour guide and he was terrific! His face seemed very familiar and probably have met him as one of the various other tours that we have done. He was very knowledgeable about the history of the pedway and he did it with great enthusiasm, very funny and sarcastic (in a good way). What a way to learn about Chicago than traveling the city through the pedway! Awesome tour, bring a water bottle and have comfy sneakers for the tour! Thanks!

Chicago Mobs and Haunts Walking Tour

Sven_Z, Mar 2026

Great experience - not only for visitors.

Bryson is a great guide who enthusiastically engaged in riveting stories about Chicago. Living in Chicagoland for 20+ years, this experience is not only for tourists and visitors - you learn about the hidden sides of Chicago. I am somewhat glad that I didn't live in the 1920's Chicago.

Haunted Chicago Booze and Boos Ghost Walking Tour

Marissa_B, Dec 2025

SO worth it!

Our tour guide was amazing! She felt like a friend just hanging out telling stories with us. She was an amazing storyteller and had a wonderful personality. Highly recommend! I felt like I learned so much. It was one of those hidden gem things to do that didnt feel touristy. The tour made me feel connected in a way to chicago. Very cool experience.

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.

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

DJ_O, Oct 2025

Great tour every time

This is my favorite tour! I’ve booked it 3 times in the past year and brought new people. It’s always a hit and everyone’s favorite. Aside from the amazing Chicago doughnuts, you get a history of the shops and some of the local building’s you pass on the way. I particularly like that history is more personal and includes nuanced stories that you don’t hear on other tours. I’ve had the same guide all 3 times, Nick, and he is GREAT. He’s funny, personable and makes a point to talk with everyone in the group as we walk around. I highly recommend this tour.

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.