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Apart from tours of neighborhoods such as Chinatown and Bronzeville, this company also runs special interest bus trips (on themes like Chicago’s theaters). Tours begin at the Chicago Cultural Center: call ahead to book.

Learn about the city’s amazing architecture on a Chicago Architecture Foundation (CAF) walking, bike, bus, or (in summer) boat tour. The fascinating trips highlight both historic and modern buildings, including Frank Lloyd Wright’s architectural legacy.

Bike Chicago will guide you through the city’s beautiful parks, neighborhoods, or along the stunning lakefront departing from either of its two locales.

Follow the trails of some of the city’s most infamous 1920s and ’30s gangster residents. Sites visited on this two-hour tour include that of the St. Valentine’s Massacre, Little Italy, and other haunts of the likes of Al Capone and John Dillinger.

Exercise your mind and your muscles by kayaking down the Chicago River while learning about the city’s history and architecture. There are gangster and ghost themed tours for both beginners and advanced paddlers.

Join a narrated tour from the Lake or Wendella boat tour to gain historical or architectural insight from a different perspective. Metro Ducks offer a wackier take with their tours onboard an amphibious WWII craft.

Run by the Chicago Office of Tourism (see Useful Information), this free service gives groups of 1 to 6 visitors a chance to benefit from the wisdom of enthusiastic local residents who know and love the city. Choose from a range of themed or neighborhood tours, and preferably book online seven days in advance.

While circling The Loop on an El train (see The El) an expert from the CAF explains the history of significant buildings and the El itself. Free tickets are available at the Chicago Cultural Center information desk on a first-come, first-served basis each day.

For a romantic ride along the waterfront, the Mag Mile, or around the Gold Coast area, flag down or book a traditional horse-drawn carriage. A flat fee is charged for a half-hour tour.

Enjoy a meal or cocktails and dancing onboard the elegant Odyssey or Spirit of Chicago cruisers. In summer, schooners Windy I and Windy II, also sail on the breeze. All depart from Navy Pier.