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Chicago Historical Tours

Explore Chicago's architecture and neighborhoods, visit the city's top historic sites, and immerse yourself in the Windy City's heritage and culture on a Gray Line Chicago historical tour.

Gray Line offers a variety of Chicago historical tours that visit the North and South sides. The North Side bus tour starts at the Palmer House Hilton and includes the Magnificent Mile, Fort Dearborn, Millenium Park, the Gold Coast and Chicago’s El Train Theatre Neighborhoods.  The South Side tour takes you past the famous Art Institute of Chicago to the site of Chess Records, where the iconic Route 66 begins. The tour includes the site of the 1893 World's Fair, Adler Planetarium and other historic sites.

Booking a Chicago historical tour with Gray Line means no worries because the name has been a trusted brand for more than 100 years. Schedule a Chicago historical tour today to explore Chicago’s famous past and glittering present including gangsters, presidents, Prohibition and even the real-world settings for Jim Butcher’s fictional supernatural hero, Harry Dresden.

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