Chicago Walking & Biking Tours

129 Results
Chicago Walking Tour: Modern Architecture

Looking for iconic Mid-Century Modern architecture? What better place than Chicago with its triumvirate of modern architects (Mies van der Rohe, Bertrand Goldberg and SOM) …More

Looking for iconic Mid-Century Modern architecture? What better place than Chicago with its triumvirate of modern architects (Mies van der Rohe, Bertrand Goldberg and SOM)...

1 hour 30 minutes Free Cancellation
4.9 (71)
from
$35
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 …More

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...

1 hour 30 minutes Free Cancellation
4.9 (51)
from
$35
Chicago Walking Tour: Connecting Past and Present

This lively overview of Chicago architecture explores iconic buildings from the 1890s to present. We'll compare and contrast a wide range of buildings with varying …More

This lively overview of Chicago architecture explores iconic buildings from the 1890s to present. We'll compare and contrast a wide range of buildings with varying...

1 hour 45 minutes Free Cancellation
5.0 (43)
from
$35
Chicago Walking Tour: Tiffany Treasures

Learn about the life and work of Louis Comfort Tiffany as we visit some of Chicago’s most magnificent art-glass and mosaic installations, each designed and …More

Learn about the life and work of Louis Comfort Tiffany as we visit some of Chicago’s most magnificent art-glass and mosaic installations, each designed and...

1 hour 30 minutes Free Cancellation
4.7 (47)
from
$35
Intro to Chicago Architecture

Immerse yourself in the fascinating history of how a muddy Midwestern outpost transformed into the global capital of architecture. Experience everything from early, classically inspired …More

Immerse yourself in the fascinating history of how a muddy Midwestern outpost transformed into the global capital of architecture. Experience everything from early, classically inspired...

1 hour 45 minutes Free Cancellation
5.0 (28)
from
$35
Chicago City Tour: Elevated Architecture Tour with Train Ticket Included

Explore Chicago’s amazing architecture from the unique perspective of elevated trains and station platforms. Learn the history behind the famous "L" system and hear how …More

Explore Chicago’s amazing architecture from the unique perspective of elevated trains and station platforms. Learn the history behind the famous "L" system and hear how...

2 hours Free Cancellation
5.0 (12)
from
$35
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

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 (5)
from
$35
Prohibition Chicago: Myth vs. Reality Walking Tour

More than 100 years later, stories of Prohibition-era Chicago still capture the public’s imagination. But the portrayal of that era in popular culture isn't always …More

More than 100 years later, stories of Prohibition-era Chicago still capture the public’s imagination. But the portrayal of that era in popular culture isn't always...

2 hours Free Cancellation
5.0 (4)
from
$35
Welcome to Chicago: The Essential City Tour with photo stops

Learn from a local as you discover Chicago’s top spots for food, drinks, architecture, and culture. On this tour, you'll explore downtown uncovering their history, …More

Learn from a local as you discover Chicago’s top spots for food, drinks, architecture, and culture. On this tour, you'll explore downtown uncovering their history,...

1 hour 30 minutes Free Cancellation
5.0 (1)
from
$35
Haunted Chicago Booze and Boos Ghost Walking Tour

Join this Chicago haunted pub tour which is a combination ghost tour and pub crawl that will take you on a walking tour to explore …More

Join this Chicago haunted pub tour which is a combination ghost tour and pub crawl that will take you on a walking tour to explore...

2 hours 30 minutes Free Cancellation
4.9 (353)
from
$36
Chicago Jewish History Landmarks Private Guided Walking Tour

Walk through Chicago’s vibrant Jewish history, from the striking Loop Synagogue to the inspiring Heald Square Monument and Jay Pritzker Pavilion. Uncover hidden gems and …More

Walk through Chicago’s vibrant Jewish history, from the striking Loop Synagogue to the inspiring Heald Square Monument and Jay Pritzker Pavilion. Uncover hidden gems and...

2 hours Free Cancellation
3.0 (1)
from
$37
Chicago Gangsters and Ghosts Walking Tour

We are the original, top-rated Gangsters and Ghosts tour! Hear the tales of the ghosts, and gangsters, that haunt the city. Explore the Chicago South …More

Likely to Sell Out
Likely to Sell Out

We are the original, top-rated Gangsters and Ghosts tour! Hear the tales of the ghosts, and gangsters, that haunt the city. Explore the Chicago South...

2 hours Free Cancellation
4.8 (348)
from
$38
Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals

The Offbeat Street Art Tour is the first tour in Chicago that truly celebrates Chicago's street art scene. No other tour takes guests out into …More

The Offbeat Street Art Tour is the first tour in Chicago that truly celebrates Chicago's street art scene. No other tour takes guests out into...

2 hours Free Cancellation
4.9 (208)
from
$40
Wicker Park Walking Tour History Trivia and Local Flavors

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 …More

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...

90 to 120 minutes Free Cancellation
5.0 (1)
from
$40
Chicago Hauntings Original Ghost Walk through Old Chicago

We wrote the book(s) on Chicago ghosts! Now in our 26th year! Ursula Bielski, our founder, has published more than a dozen volumes on Chicago's …More

We wrote the book(s) on Chicago ghosts! Now in our 26th year! Ursula Bielski, our founder, has published more than a dozen volumes on Chicago's...

2 hours
5.0 (1)
from
$40
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

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
Lincoln Park Hauntings Ghost Investigation Tour

We are Chicago's only paranormal investigation tour, and Chicago's oldest ghost and hauntings tours, founded by Ursula Bielski, Chicago's 35 year paranormal researcher and investigator. …More

We are Chicago's only paranormal investigation tour, and Chicago's oldest ghost and hauntings tours, founded by Ursula Bielski, Chicago's 35 year paranormal researcher and investigator....

2 hours 15 minutes Free Cancellation
4.9 (47)
from
$44
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

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

Embark on a profound, downtown walk-around, to discover incredible stories and secrets of the city on this not to miss feet on the street experience! …More

Embark on a profound, downtown walk-around, to discover incredible stories and secrets of the city on this not to miss feet on the street experience!...

2 hours Free Cancellation
5.0 (256)
from
$44
Downtown Chicago TV and Movie Sites Guided Walking Tour

Explore downtown Chicago through the lens of film and television on this guided walking tour featuring iconic filming locations from Ferris Bueller’s Day Off, The …More

Explore downtown Chicago through the lens of film and television on this guided walking tour featuring iconic filming locations from Ferris Bueller’s Day Off, The...

2 hours
4.4 (24)
from
$44
Chicago Seasonal Stroll Walking Tour of Holiday Attractions

There’s nothing more magical than Christmas in Chicago, & this 2hr guided Chicago Walking Tour takes you straight into the heart of it. Journey through …More

There’s nothing more magical than Christmas in Chicago, & this 2hr guided Chicago Walking Tour takes you straight into the heart of it. Journey through...

2 hours Free Cancellation
5.0 (5)
from
$45

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