Your Chicago Tour Expert

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

Book Chicago Tours & Attractions Online

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 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 river boat tour, or an architectural tour, we've got you covered.  From iconic landmarks to hidden gems and everything in between, Gray Line is Chicago's top tour expert.


2 hour tour of Chicago's Scenic North Side


2 hour Chicago tour of Chicago's Historic South Side


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

The Bucket Life Original Video Series

We say life is MORE than a to-do list...

It's a journey to live for! To celebrate the true meaning of travel, its beauty, and its ability to bring us together as a human race, Gray Line has launched a new video series: the Bucket Life.

Take a minute from your busy day to watch this video..

Or, watch the original trailer here for The Bucket Life.

Dovetail Brewery Trolley Tour

Trolley tour through Chicago’s Malt Row stopping at Dovetail Brewery for a one-hour brewery tour and beer tastings.

Go Now!

Gray Line Magazine

Things to do Thanksgiving Weekend in Chicago

Celebrating Thanksgiving in the Windy City is the perfect holiday getaway due to the numerous events it hosts. Suburban towns su…

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