Chicago Tours & Sightseeing

Best of Chicago: Premium Small Group City Tour

Discover Chicago on a 2.5-hour premium small group city tour combining landmark architecture, public art, and lakefront scenery. Begin along the Magnificent Mile and Chicago …More

Discover Chicago on a 2.5-hour premium small group city tour combining landmark architecture, public art, and lakefront scenery. Begin along the Magnificent Mile and Chicago...

2 hours 30 minutes Hotel pickup offered Free Cancellation
5.0 (48)
from
$48
Chicago Helicopter Tour: City to Shoreline

Your journey begins with a southeast departure from the Vertiport, offering early views of the city’s iconic skyline. Flying east, you’ll head toward the lakefront …More

Likely to Sell Out
Likely to Sell Out

Your journey begins with a southeast departure from the Vertiport, offering early views of the city’s iconic skyline. Flying east, you’ll head toward the lakefront...

20 to 25 minutes Free Cancellation
4.4 (33)
from
$350
Chicago Helicopter Tour: Loop Tour

Take to the skies and experience Chicago from an entirely new perspective on this extended helicopter tour showcasing the city’s most iconic landmarks, neighborhoods, and …More

Likely to Sell Out
Likely to Sell Out

Take to the skies and experience Chicago from an entirely new perspective on this extended helicopter tour showcasing the city’s most iconic landmarks, neighborhoods, and...

12 to 15 minutes Free Cancellation
4.6 (20)
from
$210
Chicago Gangsters and Ghosts Minibus Tour

Uncover the notorious history of Chicago's gangster era on this immersive bus tour that takes you through the city's most infamous landmarks. Visit the Palmer …More

Likely to Sell Out
Likely to Sell Out

Uncover the notorious history of Chicago's gangster era on this immersive bus tour that takes you through the city's most infamous landmarks. Visit the Palmer...

2 hours Free Cancellation
4.9 (18)
from
$65
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 (69)
from
$35
Small Group Tour of Chicago Neighborhoods: North and South Side

This unique tour of Chicago will allow for tourist to see most of Chicago’s 77 neighborhoods and city parks. There is no other tour that …More

This unique tour of Chicago will allow for tourist to see most of Chicago’s 77 neighborhoods and city parks. There is no other tour that...

4 hours 30 minutes Free Cancellation
4.8 (50)
from
$125
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 City Private Tours

Ready to explore Chicago like never before? Whether you have just a couple of hours or a full day, my personalized city tours offer a …More

Ready to explore Chicago like never before? Whether you have just a couple of hours or a full day, my personalized city tours offer a...

2 to 8 hours Hotel pickup offered Free Cancellation
4.8 (41)
from
$199
Chicago Insider Segway Tour

This is a tour like no other! Our newest Segway adventure is completely unique and will cover the good, the bad, the ugly and the …More

This is a tour like no other! Our newest Segway adventure is completely unique and will cover the good, the bad, the ugly and the...

2 hours Free Cancellation
4.9 (52)
from
$72
Chicago Private Custom City Tour with Hotel Pick Up

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 5 PASSENGERS.  Thank you for contacting Chicago Private Tours! We would love to help your …More

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 5 PASSENGERS.  Thank you for contacting Chicago Private Tours! We would love to help your...

3 to 4 hours Hotel pickup offered Free Cancellation
5.0 (203)
from
$539
Chicago Sunset Segway Tour

Ease into the evening with a relaxing glide through the parks and lakefront in Chicago. This evening ride offers cooler temperatures and beautiful sunset views …More

Ease into the evening with a relaxing glide through the parks and lakefront in Chicago. This evening ride offers cooler temperatures and beautiful sunset views...

1 hour 30 minutes Free Cancellation
5.0 (27)
from
$75
Chicago to Milwaukee Day Trip with Brewery Tour & City Highlights

Escape Chicago for a day and experience Milwaukee’s culture, food, and legendary beer scene. This curated day trip includes highlights such as the Harley-Davidson Museum, …More

Escape Chicago for a day and experience Milwaukee’s culture, food, and legendary beer scene. This curated day trip includes highlights such as the Harley-Davidson Museum,...

8 to 10 hours Free Cancellation
4.5 (15)
from
$125
Chicago's Lake Michigan Downtown Kayak Rental at Ohio Street Beach

Experience the best Chicago kayak rentals and Chicago SUP & paddleboard rentals from our unbeatable location at Ohio Street Beach, just steps from Navy Pier …More

Experience the best Chicago kayak rentals and Chicago SUP & paddleboard rentals from our unbeatable location at Ohio Street Beach, just steps from Navy Pier...

1 to 2 hours Free Cancellation
5.0 (25)
from
$40
Chicago Scenic Driving Tour

Chicago is a big city with a lot of activities & sightseeing. To tour the city quickly, it requires the help of a knowledgeable local …More

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

2 hours Hotel pickup offered Free Cancellation
5.0 (25)
from
$315
Haunted Ghosts & The Chicago Outfit Segway Tour

Looking for a unique Chicago tour? Glide into the city’s dark past with our unique Segway tour, where ghosts, gangsters, and true crime come to …More

Looking for a unique Chicago tour? Glide into the city’s dark past with our unique Segway tour, where ghosts, gangsters, and true crime come to...

2 hours Free Cancellation
4.8 (37)
from
$75
Chicago Hauntings Original Ghost Bus Tour

Often imitated but never matched, this 3 hour ghost bus tour with stops remains the "Best of Chicago" since its founding 23 years ago by …More

Often imitated but never matched, this 3 hour ghost bus tour with stops remains the "Best of Chicago" since its founding 23 years ago by...

3 hours Free Cancellation
4.1 (136)
from
$59
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
Chicago-Style Holiday Hike: Festive Food and Walking Tour

There’s nothing more magical than downtown Chicago during the holidays. Bobby’s Bike Hike & Food Tours—internationally recognized for quality—presents the Holiday Hike, a 3-hour guided …More

There’s nothing more magical than downtown Chicago during the holidays. Bobby’s Bike Hike & Food Tours—internationally recognized for quality—presents the Holiday Hike, a 3-hour guided...

3 hours Free Cancellation
5.0 (77)
from
$85
Chicago Lakefront Electric Bike Tour

This tour takes you along the Lakefront bike path. Which you'll be able to experience the beautiful nature that surrounds the city skyscrapers. You will …More

Likely to Sell Out
Likely to Sell Out

This tour takes you along the Lakefront bike path. Which you'll be able to experience the beautiful nature that surrounds the city skyscrapers. You will...

45 to 60 minutes Free Cancellation
5.0 (15)
from
$69
Frank Lloyd Wright Oak Park Architecture Tour from Chicago

Explore the architectural genius of Frank Lloyd Wright on a private, fully personalized tour in Chicago, home to the world’s largest collection of his buildings. …More

Likely to Sell Out
Likely to Sell Out

Explore the architectural genius of Frank Lloyd Wright on a private, fully personalized tour in Chicago, home to the world’s largest collection of his buildings....

5 hours Hotel pickup offered Free Cancellation
4.4 (10)
from
$78
Chicago River Floating Tiki Bar Cruise Friday and Saturday

Set sail for an unforgettable evening aboard the River Star or Island Time, where the drinks are flowing and the views are unmatched. Enjoy a …More

Set sail for an unforgettable evening aboard the River Star or Island Time, where the drinks are flowing and the views are unmatched. Enjoy a...

1 hour 15 minutes
4.9 (26)
from
$42

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