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Top 10 Best Chicago City Tours

Found 104 City Tours activities in Chicago. Sort by Popularity. - Page 2
 

Chicago Private Tour

(3.3 of 7 reviews)

Enjoy and appreciate Chicago with your private transportation and guide. Customize your tour and visit the most important sites and landmarks of the Windy City. Be satisfied that you experienced the most important and beautiful si... More

Free Cancellation
Private Tour
Start From $300.00
 
Chicago Private Tour

Chicago Private Tour

  • Chicago
  • Good7 reviews3.3

Enjoy and appreciate Chicago with your private transportation and guide. Customize your tour and vis....

    Free Cancellation
    Private Tour
    Start From $300.00
 
 

Chicago City Tour with Architecture River Cruise Option

(4.8 of 645 reviews)

Enjoy Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city. On this tour, you will travel through Chicago with an expert guide in a comfortable minibus, enjoy world renowned ... More

Free Cancellation
Private Tour
Start From $47.95
 
Chicago City Tour with Architecture River Cruise Option

Chicago City Tour with Architecture River Cruise Option

  • Chicago
  • Superb645 reviews4.8

Enjoy Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tou....

    Free Cancellation
    Private Tour
    Start From $47.95
 
 

Private Al Capone Gangster Tour in Chicago

(4.7 of 12 reviews)

Chicago and the history of the mob are synonymous when we look back at history. That’s why we provide an in-depth Chicago Gangster Tour that makes all of the infamous stops for our patrons.  Visit the old stomping grounds of: ... More

Free Cancellation
Private Tour
Start From $880.00
 
Private Al Capone Gangster Tour in Chicago

Private Al Capone Gangster Tour in Chicago

  • Chicago
  • Superb12 reviews4.7

Chicago and the history of the mob are synonymous when we look back at history. That’s why we prov....

    Free Cancellation
    Private Tour
    Start From $880.00
 
 

Chicago Architecture Tour: Underground Pedway and the Loop

(4.9 of 210 reviews)

This tour explores some of the best hidden details, secret buildings and spaces, and untold stories that add wonderful bits of color and texture to the overall narrative of Chicago. On this tour, we will explore the famous and mys... More

Free Cancellation
Private Tour
Start From $35.00
 
Chicago Architecture Tour: Underground Pedway and the Loop

Chicago Architecture Tour: Underground Pedway and the Loop

  • Chicago
  • Superb210 reviews4.9

This tour explores some of the best hidden details, secret buildings and spaces, and untold stories ....

    Free Cancellation
    Private Tour
    Start From $35.00
 
 

Chicago's Ultimate City Bike Tour

(4.9 of 169 reviews)

Get acquainted with Chicago’s most iconic landmarks on this riotous guided bicycle tour! Join the expert guides of Bobby’s Bike Hike, America’s longest-running city bicycle tour company, on this exciting and informative adve... More

Free Cancellation
Private Tour
Start From $54.99
 
Chicago's Ultimate City Bike Tour

Chicago's Ultimate City Bike Tour

  • Chicago
  • Superb169 reviews4.9

Get acquainted with Chicago’s most iconic landmarks on this riotous guided bicycle tour! Join the ....

    Free Cancellation
    Private Tour
    Start From $54.99
 
 

Chicago City Minibus Tour

(4.9 of 307 reviews)

Enjoy Chicago’s famous sights and fabulous skyline views on this award-winning small-group sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus, stopping at iconic locations like ear... More

Free Cancellation
Private Tour
Start From $47.95
 
Chicago City Minibus Tour

Chicago City Minibus Tour

  • Chicago
  • Superb307 reviews4.9

Enjoy Chicago’s famous sights and fabulous skyline views on this award-winning small-group sightse....

    Free Cancellation
    Private Tour
    Start From $47.95
 
 

Downtown Chicago Walking Pizza Tour

(5 of 85 reviews)

This tour is just a short walk through great Chicago neighborhoods starting near Navy Pier and the Magnificent Mile, and then heading into the Gold Coast & River North. Compare two American pizzas vs. two Italian pizzas to underst... More

Free Cancellation
Private Tour
Start From $69.00
 
Downtown Chicago Walking Pizza Tour

Downtown Chicago Walking Pizza Tour

  • Chicago
  • Superb85 reviews5

This tour is just a short walk through great Chicago neighborhoods starting near Navy Pier and the M....

    Free Cancellation
    Private Tour
    Start From $69.00
 
 

2-Hour Chicago Lakefront and Museum Campus Segway Tour

(5 of 283 reviews)

Looking for fun things to do in Chicago? Look no further! Join one of our professional guides on a scenic 6-8 mile Chicago Segway tour. Glide effortlessly through the fragrant garden paths of Grant Park to marvel at the iconic Buc... More

Free Cancellation
Private Tour
Start From $77.70
 
2-Hour Chicago Lakefront and Museum Campus Segway Tour

2-Hour Chicago Lakefront and Museum Campus Segway Tour

  • Chicago
  • Superb283 reviews5

Looking for fun things to do in Chicago? Look no further! Join one of our professional guides on a s....

    Free Cancellation
    Private Tour
    Start From $77.70
 
 

Lakefront Segway Tour in Chicago

(4.6 of 139 reviews)

Segways are amazingly fun, and Chicago's lakefront, parks, and skyline are absolutely gorgeous! Add our smart, entertaining tour guides to the mix, and you have the experience of a lifetime!... More

Free Cancellation
Private Tour
Start From $65.00
 
Lakefront Segway Tour in Chicago

Lakefront Segway Tour in Chicago

  • Chicago
  • Superb139 reviews4.6

Segways are amazingly fun, and Chicago's lakefront, parks, and skyline are absolutely gorgeous! Add ....

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

Chicago Gangsters and Ghosts Minibus Tour with Riverboat Cruise

(5 of 2 reviews)

Discover Chicago's captivating past on our top-rated Gangsters and Ghosts minibus tour + Riverboat Architecture Cruise. Explore the iconic Loop and River North neighborhoods, once dominated by notorious Italian and Irish gangs dur... More

Free Cancellation
Private Tour
Start From $99.00
 
Chicago Gangsters and Ghosts Minibus Tour with Riverboat Cruise

Chicago Gangsters and Ghosts Minibus Tour with Riverboat Cruise

  • Chicago
  • Superb2 reviews5

Discover Chicago's captivating past on our top-rated Gangsters and Ghosts minibus tour + Riverboat A....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Fulton Market Delicious Donut Adventure and Walking Food Tour

(4.9 of 31 reviews)

We begin at a local shop synonymous for their quality donuts––Do-Rite Donuts. From there we’ll walk the Randolph corridor, learning about the history of Chicago’s West Loop, a historic neighborhood which has gone through a... More

Free Cancellation
Private Tour
Start From $68.00
 
Fulton Market Delicious Donut Adventure and Walking Food Tour Likely to Sell Out

Fulton Market Delicious Donut Adventure and Walking Food Tour

  • Chicago
  • Superb31 reviews4.9

We begin at a local shop synonymous for their quality donuts––Do-Rite Donuts. From there we’ll....

    Free Cancellation
    Private Tour
    Start From $68.00
 
 

Chicago River Architecture Boat Cruise & Hop-on Hop-off Bus Tour

(3.9 of 10 reviews)

Discover Chicago by road and river with our new 48-hour Hop-on Hop-off Ticket and Shoreline Architecture Cruise combo! This ticket includes a 48-hour pass for our hop-on, hop-off Chicago sightseeing bus tour, and a pass for admiss... More

Free Cancellation
Private Tour
Start From $95.00
 
Chicago River Architecture Boat Cruise & Hop-on Hop-off Bus Tour Likely to Sell Out

Chicago River Architecture Boat Cruise & Hop-on Hop-off Bus Tour

  • Chicago
  • Very Good10 reviews3.9

Discover Chicago by road and river with our new 48-hour Hop-on Hop-off Ticket and Shoreline Architec....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

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

(5 of 90 reviews)

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! During our loop around "Da Loop" we will peel back the layers of this Great Big ... More

Special Offer
Free Cancellation
Private Tour
Start From $33.00
(Saving 25% ) $44.00
 
-25% Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour Likely to Sell Out

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

  • Chicago
  • Superb90 reviews5

Embark on a profound, downtown walk-around, to discover incredible stories and secrets of the city o....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $33.00
    (Saving 25% ) $44.00
 
 

Chicago Walking Tour: Must-See Chicago

(4.9 of 75 reviews)

Must-See Chicago is a fast-paced, 90-minute introductory tour to Chicago featuring some of its most famous buildings, including the Wrigley Building, Tribune Tower, the Art Institute of Chicago, Willis (Sears) Tower and more! Get... More

Free Cancellation
Private Tour
Start From $30.00
 
Chicago Walking Tour: Must-See Chicago Likely to Sell Out

Chicago Walking Tour: Must-See Chicago

  • Chicago
  • Superb75 reviews4.9

Must-See Chicago is a fast-paced, 90-minute introductory tour to Chicago featuring some of its most ....

    Free Cancellation
    Private Tour
    Start From $30.00
 
 

Private Chicago Scenic Driving Tour

(5 of 6 reviews)

Chicago is a big city with a lot of activities & sightseeing. To tour the city quickly, it requires the help of a knowledgeable local driving guide and that's where we step in to assist. Your Private Chicago Scenic Driving Tour wi... More

Free Cancellation
Private Tour
Start From $315.00
 
 Private Chicago Scenic Driving Tour Likely to Sell Out

Private Chicago Scenic Driving Tour

  • Chicago
  • Superb6 reviews5

Chicago is a big city with a lot of activities & sightseeing. To tour the city quickly, it requires ....

    Free Cancellation
    Private Tour
    Start From $315.00
 
 

Chicago Luxury Minibus City Tour and Architecture River Cruise

(4.7 of 15 reviews)

Experience the best of Chicago by land and water on our exclusive Luxury City Minibus Tour & Riverboat Architecture Cruise! Start with a 90-minute guided luxury minibus sightseeing tour through downtown, and seamlessly transition ... More

Free Cancellation
Private Tour
Start From $99.00
 
Chicago Luxury Minibus City Tour and Architecture River Cruise Likely to Sell Out

Chicago Luxury Minibus City Tour and Architecture River Cruise

  • Chicago
  • Superb15 reviews4.7

Experience the best of Chicago by land and water on our exclusive Luxury City Minibus Tour & Riverbo....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

3 Hours Chicago Architecture Tour - Skyscrapers and Photo Ops

(4.7 of 15 reviews)

Explore the architectural extravaganza of Chicago downtown and discover the most amazing and captivating facts about the first high-rises, city planning, and construction history. Get a unique chance to combine touring by foot a... More

Free Cancellation
Private Tour
Start From $135.00
 
3 Hours Chicago Architecture Tour - Skyscrapers and Photo Ops Likely to Sell Out

3 Hours Chicago Architecture Tour - Skyscrapers and Photo Ops

  • Chicago
  • Superb15 reviews4.7

Explore the architectural extravaganza of Chicago downtown and discover the most amazing and captiva....

    Free Cancellation
    Private Tour
    Start From $135.00
 
 

Chicago Haunted Ghosts & Gangsters Segway Tour

(4.7 of 38 reviews)

Looking for thrilling things to do in Chicago at night? Join Absolutely Chicago Segway Tours for a haunted ghost and gangster tour! Glide through downtown Chicago, discovering the city's chilling history of death, disasters, murde... More

Free Cancellation
Private Tour
Start From $78.48
 
Chicago Haunted Ghosts & Gangsters Segway Tour Likely to Sell Out

Chicago Haunted Ghosts & Gangsters Segway Tour

  • Chicago
  • Superb38 reviews4.7

Looking for thrilling things to do in Chicago at night? Join Absolutely Chicago Segway Tours for a h....

    Free Cancellation
    Private Tour
    Start From $78.48
 
 

Chicago Architecture Experience by Train

(4.9 of 26 reviews)

Chicago is often defined by its wild architecture, satisfying staples such as its famous deep dish pizza, and iconic sculptures like “The Bean” of Millennium Park. But how do you get from one attraction to another with ease? T... More

Free Cancellation
Private Tour
Start From $49.00
 
Chicago Architecture Experience by Train Likely to Sell Out

Chicago Architecture Experience by Train

  • Chicago
  • Superb26 reviews4.9

Chicago is often defined by its wild architecture, satisfying staples such as its famous deep dish p....

    Free Cancellation
    Private Tour
    Start From $49.00
 
 

Private Frank Lloyd Wright Architectural Tour by Luxury Vehicle

(3.3 of 7 reviews)

This is a drive by tour, no tour guide included, admission not included. Choose the number of hours & the vehicle type and we can help you schedule it. The list has been build with efficiency in mind and all stops are arranged in... More

Free Cancellation
Private Tour
Start From $300.00
 
Private Frank Lloyd Wright Architectural Tour by Luxury Vehicle Likely to Sell Out

Private Frank Lloyd Wright Architectural Tour by Luxury Vehicle

  • Chicago
  • Good7 reviews3.3

This is a drive by tour, no tour guide included, admission not included. Choose the number of hours....

    Free Cancellation
    Private Tour
    Start From $300.00
 
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