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Your Chicago Tour Expert

Gray Line Chicago tours will show you all the best landmarks & attractions of the city. Book your Chicago tour tickets online today!

Free Cancellation

No Hidden Fees

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COVID-19 Update: Gray Line Chicago will be closed until further notice.  We look forward to showing you the best of the Windy City again soon.


Chicago Tours & Sightseeing Attractions

Tour all of Chicago's top sightseeing attractions and visit the must-see things to do in Chicago with your local expert guide.

Who We Are

Since 1910, Gray Line has been a trusted provider of traveler experiences and sightseeing tours in the world’s most sought after locations. Helping you discover a new destination – that’s our passion! With hundreds of local offices, our team of on-site experts is there to help you see the sights and do the things that you just can’t miss.  Our Chicago tour experts at Grayline Chicago are standing by to help create memories that will last a lifetime!

What We Do

Discover Chicago and its historic Architecture, Vibrant Neighborhoods, Parks, Museums, Lakefront and more!  There are many who can take you sightseeing, but only with Gray Line will you feel like a local.  Whether you prefer a guided tour of Chicago, a Chicago bus tour, or a Chicago Architecture River Boat Tour, we've got you covered.  From iconic landmarks to hidden gems and everything in between, Gray Line offers a variety of Chicago tours to choose from.

Featured Tours

HISTORIC CHICAGO - South Side Tour and Chicago Style Pizza

HISTORIC CHICAGO - South Side Tour and Chicago Sty

Rate from HISTORIC CHICAGO - South Side Tour and Chicago Style Pizza
2 hours
Free Cancellation
Fully refundable when canceled up to 24 hours prior to departure.
50.95

From

BEST OF CHICAGO - Grand Tour

BEST OF CHICAGO - Grand Tour

Rate from BEST OF CHICAGO - Grand Tour
4 Hours
Free Cancellation
Fully refundable when canceled up to 24 hours prior to departure.
52.95

From

BEST OF CHICAGO - Grand Tour & 360 CHICAGO Observation Deck

BEST OF CHICAGO - Grand Tour & 360 CHICAGO

Rate from BEST OF CHICAGO - Grand Tour & 360 CHICAGO Observation Deck
4 hours
Free Cancellation
Fully refundable when canceled up to 24 hours prior to departure.
50.95

From

SCENIC CHICAGO - North Side Tour

SCENIC CHICAGO - North Side Tour

Rate from SCENIC CHICAGO - North Side Tour
2 hours
Free Cancellation
Fully refundable when canceled up to 24 hours prior to departure.
34.95

From

HISTORIC CHICAGO - South Side Tour & 360 CHICAGO Observation Deck

HISTORIC CHICAGO - South Side Tour & 360 CHICAGO O

Rate from HISTORIC CHICAGO - South Side Tour & 360 CHICAGO Observation Deck
2 hours
Free Cancellation
Fully refundable when canceled up to 24 hours prior to departure.
49.95

From

SCENIC CHICAGO - North Side Tour & 360 CHICAGO Observation Deck

SCENIC CHICAGO - North Side Tour & 360 CHICAGO Obs

Rate from SCENIC CHICAGO - North Side Tour & 360 CHICAGO Observation Deck
2 hours
Free Cancellation
Fully refundable when canceled up to 24 hours prior to departure.
49.95

From

 

Discover Chicago

#FindAReasonToGo

2 hour tour of Chicago's Scenic North Side

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#FindAReasonToGo

2 hour Chicago tour of Chicago's Historic South Side

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A comprehensive tour of everything Chicago has to offer! North & South Tours combined

Chicago Grand Tour

See the BEST of Chicago on the Grand Tour where you'll see and learn about our beautfiul parks, architecture, history, and more!

VIEW TOUR DETAILS

Need a Ride to/from the Airport?

Gray Line Chicago has partnered with GO Airport Express to provide safe, convenient, and affordable transportation to/from Chicago's airports.

BOOK A RIDE
 

Gray Line Magazine

Getting Ready to Re-Open

This will be a journey and we at Gray Line Chicago are thoughtfully preparing for this next phase as we adapt our tour operation…

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