Walking Tours in Chicago
Top 10 Best Chicago Walking Tours
Found 151 Walking Tours activities in Chicago. Sort by Popularity. - Page 4River North Food Walking Tour
On our 3 hour food walking tour of Chicago, you will taste delectable foods from 5 different delicious places. Tease your tastebuds as you savor foods from Chicago's best deep dish pizza restaurant, Rick Bayless' amazing Mexican f... More

River North Food Walking Tour
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Chicago
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Superb76 reviews4.7
On our 3 hour food walking tour of Chicago, you will taste delectable foods from 5 different delicio....
Chicago Riverwalk & Millennium Park Self-Guided Audio Tour Bundle
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 cityâ€... More
Private Tour

Chicago Riverwalk & Millennium Park Self-Guided Audio Tour Bundle
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Chicago
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Superb76 reviews4.7
Explore the surprising beauty and history of the Windy City with this combo tour of Chicago’s Mill....
Private Tour
Chicago Self-Guided Audio Tour
Embark on an exhilarating journey through Chicago, the "City of Big Shoulders," with our comprehensive self-guided audio tour. From the bustling Loop to the serene shores of Lake Michigan, uncover the rich tapestry of history, cul... More
Private Tour

Chicago Self-Guided Audio Tour
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Chicago
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Very Good9 reviews3.9
Embark on an exhilarating journey through Chicago, the "City of Big Shoulders," with our comprehensi....
Private Tour
Professional Photo Shoot in Chicago
Professional photo shoot in unique Chicago locations. The Photo Experience will create amazing photo memories from your visit. You will be able to see undiscovered locations and get the best photo story from your Chicago visit. We... More
Private Tour

Professional Photo Shoot in Chicago
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Chicago
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Exellent8 reviews4.4
Professional photo shoot in unique Chicago locations. The Photo Experience will create amazing photo....
Private Tour
Historic Homes and Cottages of Wicker Park Walking Tour
Much of the historical information shared on this tour is unknown to most attendees. This tour also shows everything from the gritty to the pretty, from the mundane to the magnificent.... More
Private Tour

Historic Homes and Cottages of Wicker Park Walking Tour
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Chicago
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Superb34 reviews5
Much of the historical information shared on this tour is unknown to most attendees. This tour also ....
Private Tour
Chicago Half-Day Walking Food Tour with Free Bike or Kayak Rental
Ready for the ultimate day out in Chicago? We’ll embark on an unforgettable Chicago journey, where iconic flavors like Chicago Pizza, Hot Dogs, Italian Beef, Chicago-mix Popcorn, and the original Brownie await. Opt for the VIP C... More
Private Tour

Chicago Half-Day Walking Food Tour with Free Bike or Kayak Rental
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Chicago
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Superb1 review5
Ready for the ultimate day out in Chicago? We’ll embark on an unforgettable Chicago journey, where....
Private Tour
1 Hour Photoshoot in Chicago
In this photoshoot you will have most iconic and important places in downtown Chicago, places where you need to have a photo with , and in a unique way with your own personal photographer. We will have the most photogenic and beau... More
Private Tour

1 Hour Photoshoot in Chicago
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Chicago
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Superb1 review5
In this photoshoot you will have most iconic and important places in downtown Chicago, places where ....
Private Tour
Best of Chicago: Architecture & Highlights City Private Tour
Get the best of Chicago with a local guide on this walking tour featuring the city’s best neighborhoods, top attractions, and the Chicago ‘L’! We’ll start by exploring the Chicago Loop, home to an array of mind-blowing ar... More
Private Tour

Best of Chicago: Architecture & Highlights City Private Tour
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Chicago
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Superb95 reviews4.9
Get the best of Chicago with a local guide on this walking tour featuring the city’s best neighbor....
Private Tour

Eastside Chicago The Heist Exploration Game and Tour
Play a city game where you will follow clues to discover amazing places and local stories in Chicago. You’ll tour Chicago’s famous Millenium Park and learn about the iconic works of art that populate the area on your way to r... More
Free Cancellation
Private Tour
(Saving 20% )

Eastside Chicago The Heist Exploration Game and Tour
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Chicago
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Very Good9 reviews3.9
Play a city game where you will follow clues to discover amazing places and local stories in Chicago....
Free Cancellation
Private Tour
(Saving 20% )
Chicago Walking Tour: The Magnificent Mile
Discover how a dirt road known as Pine Street transformed into a "Paris on the Prairie" and later into the Magnificent Mile, the city’s premier shopping district. Hear the secrets and stories behind the striking buildings on Nor... More
Private Tour

Chicago Walking Tour: The Magnificent Mile
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Chicago
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Superb33 reviews4.8
Discover how a dirt road known as Pine Street transformed into a "Paris on the Prairie" and later in....
Private Tour
Chicago Walking Tour: Historic Skyscrapers
Chicago is home to some of the world’s earliest skyscrapers. Get an up-close look at these 19th Century marvels, learn about innovations used to build them and discover how they transformed Chicago into a center of skyscraper de... More
Private Tour

Chicago Walking Tour: Historic Skyscrapers
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Chicago
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Superb66 reviews4.8
Chicago is home to some of the world’s earliest skyscrapers. Get an up-close look at these 19th Ce....
Private Tour
2 Hour Magnificent Chicago Tour with Photos and Popcorn
Be welcomed and greeted in Chicago from a TRUE native of the city. Experience the vibrant history and culture of the city while being professional photographed, and enjoying Chicago's famous Garrett's popcorn. This tour is lead by... More
Private Tour

2 Hour Magnificent Chicago Tour with Photos and Popcorn
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Chicago
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Superb1 review5
Be welcomed and greeted in Chicago from a TRUE native of the city. Experience the vibrant history an....
Private Tour
Chicago-Style Holiday Hike: Festive Food and Walking Tour
There’s nothing more magical than downtown Chicago during the holiday season. Bobby’s Holiday Hike is a 3hr guided walking and food tour through the Chicago Loop, brought to you by Bobby's Bike Hike, internationally recognize... More
Private Tour

Chicago-Style Holiday Hike: Festive Food and Walking Tour
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Chicago
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Superb68 reviews4.9
There’s nothing more magical than downtown Chicago during the holiday season. Bobby’s Holiday H....
Private Tour
Chicago in a Day: Food and Architecture Private Walking Tour
Get the whole Chicago experience combining our Chicago Architecture & Highlights Tour and Chicago Food Tour: Deep Roots to Deep Dish! Our two-part tour begins by exploring the heart of downtown Chicago - with its iconic architect... More
Private Tour

Chicago in a Day: Food and Architecture Private Walking Tour
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Chicago
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Superb52 reviews5
Get the whole Chicago experience combining our Chicago Architecture & Highlights Tour and Chicago Fo....
Private Tour
Welcome to Chicago: Private Half-Day Tour with 360 Observation Deck
On your Private Chicago Half Day Highlights tour, visit all the city’s major sites, including favourites such as the Magnificent Mile, Millennium Park and Hancock Tower. Your guide is a local who has plenty of tales about Chicag... More
Private Tour

Welcome to Chicago: Private Half-Day Tour with 360 Observation De....
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Chicago
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Superb2 reviews5
On your Private Chicago Half Day Highlights tour, visit all the city’s major sites, including favo....
Private Tour
Chicago Insta Walk with Digital and Polaroid Photoshoot
Insta Walk offers you a lot of stylish photos, shooting angles and ideas. This easy, relaxed and friendly walk will open Chicago for you from a new perspective! Throughout the tour, I'll use iPhone and Polaroid cameras to capture... More
Private Tour

Chicago Insta Walk with Digital and Polaroid Photoshoot
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Chicago
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Superb26 reviews5
Insta Walk offers you a lot of stylish photos, shooting angles and ideas. This easy, relaxed and fri....
Private Tour
Prairie Avenue Haunted History Tour and Ghost Hunt
Chicago's original Millionaire's Row, meet the ghosts of the Gilded Age. Marshall Field, George Pullman, Philip Armour, and many more used to live in this amazing area, the most desirable address in the city before the fire. Man... More
Private Tour

Prairie Avenue Haunted History Tour and Ghost Hunt
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Chicago
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Superb11 reviews5
Chicago's original Millionaire's Row, meet the ghosts of the Gilded Age. Marshall Field, George Pull....
Private Tour
Chicago Neighborhood Food Private Walking Tour
This Chicago food tour gives you the chance to explore the city’s foodie scene to its fullest. Explore legendary bakeries in neighborhoods around the city. You'll discover Chicago’s immigrant roots with incredible food from ar... More
Private Tour

Chicago Neighborhood Food Private Walking Tour
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Chicago
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Superb21 reviews4.9
This Chicago food tour gives you the chance to explore the city’s foodie scene to its fullest. Exp....
Private Tour
Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago
Enjoy a private 2-hour walking tour with Belgian-American tour guide Leentje. She will introduce you to the city she calls home since 2014. Every tour is different and custom-made. Tours are available in English, French, or Dutch.... More
Private Tour

Your Way or the Highway: 2-hour Customized Private Walking Tour i....
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Chicago
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Superb34 reviews5
Enjoy a private 2-hour walking tour with Belgian-American tour guide Leentje. She will introduce you....
Private Tour
Chicago Walking Tour: Art Deco Skyscrapers Loop
View Art Deco masterpieces built in the heart of Chicago’s financial district during the Roaring '20s. Learn how Art Deco reflected the era’s fun-loving optimism with lavish materials and geometric ornament. Discover the orig... More
Private Tour

Chicago Walking Tour: Art Deco Skyscrapers Loop
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Chicago
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Superb131 reviews4.8
View Art Deco masterpieces built in the heart of Chicago’s financial district during the Roaring '....
Private Tour