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Chicago Sightseeing Tours

Gray Line offers a variety of Chicago 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!

3 products, viewing 1 - 3
  • BEST OF CHICAGO - Grand Tour

    BEST OF CHICAGO - Grand Tour

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

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

    From

    52.95
  • HISTORIC CHICAGO - South Side Tour

    HISTORIC CHICAGO - South Side Tour

    2 hour tour of Chicago's Historic South Side

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

    From

    34.95
  • SCENIC CHICAGO - North Side Tour

    SCENIC CHICAGO - North Side Tour

    2 hour tour of Chicago's Scenic North Side

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

    From

    34.95