Chicago Sightseeing Tours

Grayline Chicago offers a variety of sightseeing tours for visitors and locals to enjoy.   See Chicago's famous landmarks, parks, and waterfront with spectacular views aboard our touring buses.

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, our Chicago tour experts have crafted the perfect experience for you to immerse yourself in the best the Windy City has to offer.

Book your Chicago sightseeing tours with one of the most trusted tour operators in the business.  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 Chicago – that’s our passion!  Call or book online today!

12 products, viewing 11 - 12

SCENIC CHICAGO - North Side Tour & 360 CHICAGO Observation Deck

2 hour sightseeing tour of Chicago's Scenic North Side plus entry to 360 Chicago Observation Deck

From 52.95 Duration: 2 hours
Easy Cancellation

Land & River Architecture Tour featuring SCENIC CHICAGO - North Side Tour

2-hour tour of Chicago's Scenic North Side plus 90-minute Architectural River Tour aboard Chicago Line Cruises

From 76.95 Duration: 4 hours
Easy Cancellation