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Top Chicago Walking Tours

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Chicago Tours

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Private Chicago Loop Architecture Walking Tour

Explore the historic Loop District of Chicago on a private walking tour that delves into the city's architectural legacy. With an expert guide, visit iconic …More

5.0 (22)

Private Chicago Loop Architecture Walking Tour

Explore the historic Loop District of Chicago on a private walking tour that delves into the city's architectural legacy. With an expert guide, visit iconic...

120 to 150 minutes Free Cancellation
5.0 (22)
from
$71
Chicago Loop Walking Tour

The Loop is the heartbeat of downtown Chicago! It is filled with great architecture, drop-dead gorgeous interiors and fantastic works of art from famous artists. …More

4.9 (56)

Chicago Loop Walking Tour

The Loop is the heartbeat of downtown Chicago! It is filled with great architecture, drop-dead gorgeous interiors and fantastic works of art from famous artists....

2 hours Free Cancellation
4.9 (56)
from
$60
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 …More

Likely to Sell Out
Likely to Sell Out
5.0 (3)

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...

3 hours Free Cancellation
5.0 (3)
from
$109
The Deep Pockets Of Graceland Cemetery Walking Tour

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 …More

4.9 (13)

The Deep Pockets Of Graceland Cemetery Walking Tour

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...

1 hour 30 minutes Free Cancellation
4.9 (13)
from
$45
Chicago Full-Day Walking Food Tour with Free Bike or Kayak Rental

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 …More

Likely to Sell Out
Likely to Sell Out
5.0 (3)

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

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...

5 hours Free Cancellation
5.0 (3)
from
$99
A Woman's Place: The Chicago Women's History Walking Tour

Forget the history you learned in school—Chicago’s story looks very different when told through the women who helped shape it. On this captivating 2-hour walking …More

Likely to Sell Out
Likely to Sell Out
5.0 (4)

A Woman's Place: The Chicago Women's History Walking Tour

Forget the history you learned in school—Chicago’s story looks very different when told through the women who helped shape it. On this captivating 2-hour walking...

2 hours Free Cancellation
5.0 (4)
from
$35
The Art Institute in Chicago Highlights Tour & Photoshoot

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 & …More

5.0 (5)

The Art Institute in Chicago Highlights Tour & Photoshoot

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 &...

1 hour 15 minutes Free Cancellation
5.0 (5)
from
$101
Downtown Chicago Guided Walking Tour Semi-Private 12ppl Max

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 …More

5.0 (5)

Downtown Chicago Guided Walking Tour Semi-Private 12ppl Max

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 hours 30 minutes Free Cancellation
5.0 (5)
from
$43
Chicago Walking Tour of Highlights with Free Bike or Kayak Rental

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 …More

5.0 (7)

Chicago Walking Tour of Highlights with Free Bike or Kayak Rental

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...

2 hours Free Cancellation
5.0 (7)
from
$50
Explore the Historic Old Post Office in Chicago

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 …More

5.0 (27)

Explore the Historic Old Post Office in Chicago

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...

1 hour 30 minutes Free Cancellation
5.0 (27)
from
$15
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 …More

5.0 (12)

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...

2 hours 20 minutes
5.0 (12)
from
$44
Chicago Photography Masterclass Private Photography Lesson

This tour is special because it combines a personalized street and night tour experience with expert photography guidance in Chicago. You’ll explore both iconic landmarks …More

Likely to Sell Out
Likely to Sell Out
5.0 (1)

Chicago Photography Masterclass Private Photography Lesson

This tour is special because it combines a personalized street and night tour experience with expert photography guidance in Chicago. You’ll explore both iconic landmarks...

3 hours Free Cancellation
5.0 (1)
from
$110
Private Chicago Foodie Tour

Taste your way through Chicago on this private half-day walking food tour! Savor local favorites like Portillo’s hot dogs, Al’s Italian Beef, deep dish pizza, …More

5.0 (6)

Private Chicago Foodie Tour

Taste your way through Chicago on this private half-day walking food tour! Savor local favorites like Portillo’s hot dogs, Al’s Italian Beef, deep dish pizza,...

4 hours Free Cancellation
5.0 (6)
from
$288
Private Vacation Photoshoot with Photographer in Chicago

⭐ Top-Rated Vacation Photoshoots 2025 We’re not just photographers, we’re storytellers capturing your holiday exactly as it feels. With over six years of experience photographing …More

Likely to Sell Out
Likely to Sell Out
4.0 (4)

Private Vacation Photoshoot with Photographer in Chicago

⭐ Top-Rated Vacation Photoshoots 2025 We’re not just photographers, we’re storytellers capturing your holiday exactly as it feels. With over six years of experience photographing...

1 hour Free Cancellation
4.0 (4)
from
$137
Chicago Downtown TV and Movie Sites Private 2-Hour Walking Tour

Explore over 30 iconic movie and TV locations on this two-hour walking tour of downtown Chicago! Visit sites from Ferris Bueller’s Day Off, The Untouchables, …More

4.8 (4)

Chicago Downtown TV and Movie Sites Private 2-Hour Walking Tour

Explore over 30 iconic movie and TV locations on this two-hour walking tour of downtown Chicago! Visit sites from Ferris Bueller’s Day Off, The Untouchables,...

2 hours
4.8 (4)
from
$87
Private Chicago Architecture Walking Tour

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 …More

4.8 (6)

Private Chicago Architecture Walking Tour

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...

3 hours Free Cancellation
4.8 (6)
from
$211
Chicago Local Brewery Expedition with Homemade Guacamole

We'll explore five (5) of our favorite, Handcrafted Local Micro Breweries in two special locations of the historic, Chicago landmark district, Fulton Market; which used …More

5.0 (4)

Chicago Local Brewery Expedition with Homemade Guacamole

We'll explore five (5) of our favorite, Handcrafted Local Micro Breweries in two special locations of the historic, Chicago landmark district, Fulton Market; which used...

1 hour 30 minutes Free Cancellation
5.0 (4)
from
$53
Explore Chicago Black Culinary Heritage

The Experience is more than a food tour. It is an immersive cultural experience that combines food, history, architecture, and storytelling in one of Chicago’s …More

5.0 (6)

Explore Chicago Black Culinary Heritage

The Experience is more than a food tour. It is an immersive cultural experience that combines food, history, architecture, and storytelling in one of Chicago’s...

2 hours 45 minutes Free Cancellation
5.0 (6)
from
$75
Chicago Foods Tour with The Loop, Skyline, Millennium Park

Delve into Chicago’s one-of-a-kind cuisine and learn something that you would never expect on this small-group Secret Food Tour. Eat your way through the most …More

4.6 (5)

Chicago Foods Tour with The Loop, Skyline, Millennium Park

Delve into Chicago’s one-of-a-kind cuisine and learn something that you would never expect on this small-group Secret Food Tour. Eat your way through the most...

3 hours Free Cancellation
4.6 (5)
from
$145
️ Chicago Instagram Walking Tour (Private & All- Inclusive)

Our Chicago Walking Instagram Tour will take you to the most Instagrammable spots in Chicago all in one day. If you are looking for a …More

5.0 (2)

️ Chicago Instagram Walking Tour (Private & All- Inclusive)

Our Chicago Walking Instagram Tour will take you to the most Instagrammable spots in Chicago all in one day. If you are looking for a...

4 hours Free Cancellation
5.0 (2)
from
$236

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