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Top 10 Best Chicago City Tours

Found 104 City Tours activities in Chicago. Sort by Popularity.
 

Chicago Architecture River Cruise

(4.8 of 13,969 reviews)

Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. This architectural tour takes you down the main branch of the river, up the north branch to the East Bank Club, and then south pas... More

Free Cancellation
Start From $48.78
 
Chicago Architecture River Cruise

Chicago Architecture River Cruise

  • Chicago
  • Superb13,969 reviews4.8

Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. ....

    Free Cancellation
    Start From $48.78
 
 

Chicago River 45-Minute Architecture Tour from Magnificent Mile

(4.7 of 1,829 reviews)

Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich history and architectural heritage feat... More

Free Cancellation
Start From $28.00
 
Chicago River 45-Minute Architecture Tour from Magnificent Mile Likely to Sell Out

Chicago River 45-Minute Architecture Tour from Magnificent Mile

  • Chicago
  • Superb1,829 reviews4.7

Experience Chicago's legendary architecture and the exceptional architects who created this ever-cha....

    Free Cancellation
    Start From $28.00
 
 

Chicago Architecture Center River Cruise aboard Chicago's First Lady

(4.9 of 3,363 reviews)

The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only Chicago architecture boat tour led by highly trained expert docents. On t... More

Free Cancellation
Start From $54.00
 
Chicago Architecture Center River Cruise aboard Chicago's First Lady Likely to Sell Out

Chicago Architecture Center River Cruise aboard Chicago's First L....

  • Chicago
  • Superb3,363 reviews4.9

The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold stan....

    Free Cancellation
    Start From $54.00
 
 

Chicago: Gangsters and Ghosts Walking Tour

(4.8 of 6,994 reviews)

Interested in exploring Chicago from the perspective of ghosts and gangsters? Want to really immerse yourself in the history of this great American city, right from the locations that started it all? This tour visits the location... More

Free Cancellation
Start From $35.00
 
Chicago: Gangsters and Ghosts Walking Tour Likely to Sell Out

Chicago: Gangsters and Ghosts Walking Tour

  • Chicago
  • Superb6,994 reviews4.8

Interested in exploring Chicago from the perspective of ghosts and gangsters? Want to really immerse....

    Free Cancellation
    Start From $35.00
 
 

Chicago Favorites Ultimate Food and Walking Tour

(4.8 of 1,382 reviews)

The perfect tour for first timers to Chicago or those who want to explore Chicago's famous foods along with the city's top attractions, all on one tour. Stroll the beautiful streets of downtown Chicago & taste the Windy City’s f... More

Free Cancellation
Start From $84.99
 
Chicago Favorites Ultimate Food and Walking Tour Likely to Sell Out

Chicago Favorites Ultimate Food and Walking Tour

  • Chicago
  • Superb1,382 reviews4.8

The perfect tour for first timers to Chicago or those who want to explore Chicago's famous foods alo....

    Free Cancellation
    Start From $84.99
 
 

Lake Michigan Skyline Cruise in Chicago

(4.5 of 761 reviews)

Embark on an unforgettable journey along Lake Michigan and marvel at Chicago's iconic lakefront sights and attractions. Cruise along Lake Michigan and enjoy stunning views of Chicago's renowned skyscrapers from a unique vantage p... More

Free Cancellation
Start From $32.50
 
Lake Michigan Skyline Cruise in Chicago Likely to Sell Out

Lake Michigan Skyline Cruise in Chicago

  • Chicago
  • Exellent761 reviews4.5

Embark on an unforgettable journey along Lake Michigan and marvel at Chicago's iconic lakefront sigh....

    Free Cancellation
    Start From $32.50
 
 

Chicago Lake and River Architecture Tour

(4.7 of 2,010 reviews)

An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursion tells the story of more than 200 years of fascinating social, cultural and political history, and explores more than a century ... More

Free Cancellation
Start From $45.00
 
Chicago Lake and River Architecture Tour Likely to Sell Out

Chicago Lake and River Architecture Tour

  • Chicago
  • Superb2,010 reviews4.7

An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursi....

    Free Cancellation
    Start From $45.00
 
 

Private 45-Minute Chicago Skyline Helicopter Tour

(4.8 of 119 reviews)

This tour is unique as it offers the ability for you and two of your friends or family (a total of 3 passengers) to experience what it is like to fly over the city of Chicago on a 45 minute thrill seeking guided tour. The price is... More

Free Cancellation
Private Tour
Start From $849.00
 
Private 45-Minute Chicago Skyline Helicopter Tour Likely to Sell Out

Private 45-Minute Chicago Skyline Helicopter Tour

  • Chicago
  • Superb119 reviews4.8

This tour is unique as it offers the ability for you and two of your friends or family (a total of 3....

    Free Cancellation
    Private Tour
    Start From $849.00
 
 

Chicago's Chinatown Food and Walking Tour

(4.9 of 357 reviews)

Few neighborhoods in America combine such delicious cuisine with such fascinating history as Chicago’s Chinatown. Join Bobby’s Bike Hike, whose food tours in just the past year have ranked as Top 10 in America by USA Today and... More

Free Cancellation
Private Tour
Start From $79.99
 
Chicago's Chinatown Food and Walking Tour Likely to Sell Out

Chicago's Chinatown Food and Walking Tour

  • Chicago
  • Superb357 reviews4.9

Few neighborhoods in America combine such delicious cuisine with such fascinating history as Chicago....

    Free Cancellation
    Private Tour
    Start From $79.99
 
 

Chicago Gangsters and Ghosts Luxury Minibus Tour

(4.9 of 36 reviews)

Discover Chicago's captivating past on our top-rated Gangsters and Ghosts luxury minibus tour, exploring the iconic Loop and River North neighborhoods, once dominated by notorious Italian and Irish gangs during Prohibition. Delv... More

Free Cancellation
Private Tour
Start From $65.00
 
Chicago Gangsters and Ghosts Luxury Minibus Tour Likely to Sell Out

Chicago Gangsters and Ghosts Luxury Minibus Tour

  • Chicago
  • Superb36 reviews4.9

Discover Chicago's captivating past on our top-rated Gangsters and Ghosts luxury minibus tour, explo....

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

Chicago Craft Brewery Barrel Bus Tour

(4.9 of 267 reviews)

There’s never been a better time to be a beer drinker — and Chicago, with its thriving brewery scene and many destination-worthy beer bars, is the perfect city for suds lovers. Visit three of its craft breweries on this all-in... More

Free Cancellation
Private Tour
Start From $99.60
 
Chicago Craft Brewery Barrel Bus Tour Likely to Sell Out

Chicago Craft Brewery Barrel Bus Tour

  • Chicago
  • Superb267 reviews4.9

There’s never been a better time to be a beer drinker — and Chicago, with its thriving brewery s....

    Free Cancellation
    Private Tour
    Start From $99.60
 
 

Chicago-Style Holiday Hike: Festive Food and Walking Tour

(4.9 of 54 reviews)

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

Free Cancellation
Private Tour
Start From $79.99
 
Chicago-Style Holiday Hike: Festive Food and Walking Tour Likely to Sell Out

Chicago-Style Holiday Hike: Festive Food and Walking Tour

  • Chicago
  • Superb54 reviews4.9

There’s nothing more magical than downtown Chicago during the holiday season. Bobby’s Holiday H....

    Free Cancellation
    Private Tour
    Start From $79.99
 
 

2-Hour Guided Segway Tour of Chicago

(4.8 of 418 reviews)

2 hours of being a kid again!!! Take a Segway tour with us and discover how beautiful Chicago truly is. Ride through some of Chicago's most popular destinations with an experienced guide. We will glide through scenic and historic ... More

Free Cancellation
Private Tour
Start From $65.00
 
2-Hour Guided Segway Tour of Chicago Likely to Sell Out

2-Hour Guided Segway Tour of Chicago

  • Chicago
  • Superb418 reviews4.8

2 hours of being a kid again!!! Take a Segway tour with us and discover how beautiful Chicago truly ....

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

Chicago Pizza Tour

(4.9 of 395 reviews)

Enjoy Chicago’s only bus guided neighborhood pizza tour.  Eat like a local as you travel off the beaten path into Chicago neighborhoods to savor the best pizza.  Your local guide will teach you the science behind ingredient se... More

Free Cancellation
Private Tour
Start From $89.00
 
Chicago Pizza Tour Likely to Sell Out

Chicago Pizza Tour

  • Chicago
  • Superb395 reviews4.9

Enjoy Chicago’s only bus guided neighborhood pizza tour.  Eat like a local as you travel off the ....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Chicago Helicopter 10-Minute Tour for up to Three Passengers

(4.1 of 9 reviews)

A helicopter tour of downtown Chicago is a unique and thrilling way to experience the Windy City. From high up in the sky, you'll be able to take in breathtaking panoramic views of Chicago's iconic skyline, world-famous landmarks,... More

Free Cancellation
Private Tour
Start From $375.00
 
Chicago Helicopter 10-Minute Tour for up to Three Passengers Likely to Sell Out

Chicago Helicopter 10-Minute Tour for up to Three Passengers

  • Chicago
  • Exellent9 reviews4.1

A helicopter tour of downtown Chicago is a unique and thrilling way to experience the Windy City. Fr....

    Free Cancellation
    Private Tour
    Start From $375.00
 
 

Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

(4.9 of 616 reviews)

Taste all of Chicago’s classic eats on this 4 1/2 hour guided bicycle tour! Join the expert tour guides of Bobby’s Bike Hike, America’s longest-running city bike tour company, on this exciting and informative adventure which... More

Free Cancellation
Private Tour
Start From $89.00
 
Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour Likely to Sell Out

Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

  • Chicago
  • Superb616 reviews4.9

Taste all of Chicago’s classic eats on this 4 1/2 hour guided bicycle tour! Join the expert tour g....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Original Chicago Architecture Interiors Tour: Dazzling Interiors

(5 of 981 reviews)

UPDATE 2024: Don't be fooled by the copycats out there offering shady copies of our award-winning tours for $1 cheaper! There's only one company that's exclusively offered interiors-themed tours in Chicago for more than a decade, ... More

Free Cancellation
Private Tour
Start From $35.00
 
Original Chicago Architecture Interiors Tour: Dazzling Interiors Likely to Sell Out

Original Chicago Architecture Interiors Tour: Dazzling Interiors

  • Chicago
  • Superb981 reviews5

UPDATE 2024: Don't be fooled by the copycats out there offering shady copies of our award-winning to....

    Free Cancellation
    Private Tour
    Start From $35.00
 
 

Chicago Walking Food Tour With Secret Food Tours

(4.9 of 630 reviews)

On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the people who built this city. You'll experience all the city's biggest food hits, many dishes with roots dating back over 150 years... More

Free Cancellation
Private Tour
Start From $89.00
 
Chicago Walking Food Tour With Secret Food Tours Likely to Sell Out

Chicago Walking Food Tour With Secret Food Tours

  • Chicago
  • Superb630 reviews4.9

On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the ....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Chicago's Delicious Donut Adventure with Underground Donut Tour

(4.9 of 1,155 reviews)

We've always had a passion for donuts, but only recently did we realize just how many others do too. And when looking around, we didn't see anything that truly celebrated donuts in all their glory, hence the Underground Donut Tour... More

Free Cancellation
Private Tour
Start From $68.00
 
Chicago's Delicious Donut Adventure with Underground Donut Tour Likely to Sell Out

Chicago's Delicious Donut Adventure with Underground Donut Tour

  • Chicago
  • Superb1,155 reviews4.9

We've always had a passion for donuts, but only recently did we realize just how many others do too.....

    Free Cancellation
    Private Tour
    Start From $68.00
 
 

Chicago Small Group Food Tour

(4.7 of 69 reviews)

Experience the best travel stories for yourself! Join a local expert and uncover hidden gems. Join us for the ultimate foodie adventure in Chicago’s historic River North area alongside a local guide who can show you the best spo... More

Free Cancellation
Private Tour
Start From $68.83
 
Chicago Small Group Food Tour Likely to Sell Out

Chicago Small Group Food Tour

  • Chicago
  • Superb69 reviews4.7

Experience the best travel stories for yourself! Join a local expert and uncover hidden gems. Join u....

    Free Cancellation
    Private Tour
    Start From $68.83
 
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