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 Grayline Chicago historical tour.

Grayline offers a variety of historic bus tours that visit the North and South sides of Chicago. 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 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.