Discover Chicago on Foot: Essential Free Tour Guide

🏙️ 1. Free Chicago Essentials Tour: Art & Skyscrapers

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Perfect for first-time visitors. This tour takes you through Chicago’s architectural icons and green spaces—from Picasso’s art to the reflections on the famous “Bean.”

📍 Highlights along the route:

• Daley Plaza: Tour begins at Picasso’s enigmatic sculpture, an urban art icon.
• Theater District: Explore the origins of skyscrapers and the history of Willis Tower.
• Art Institute of Chicago (exterior): Marvel at one of the world’s greatest art museums, founded in 1879.
• Millennium Park: Stroll through the lakefront garden, including the iconic “Cloud Gate” (The Bean).
• Wrigley Building: Tour ends here, crossing the Chicago River for one of the city’s most famous photos.

ℹ️ Practical Details:

• Duration: 2 h 30 min.
• Meeting point: Daley Plaza, by the Picasso Statue.
• Endpoint: Wrigley Building.
• Pets: Allowed.

🕵️ 2. Chicago Crime & Mob Tour (Paid Tour)

Uncover Chicago's dark past on this bus tour, exploring the historic crime scenes of notorious gangsters like Al Capone, John Dillinger, and the city's first serial killer, H. H. Holmes. A chilling and fascinating experience awaits.

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📍 Key Itinerary Stops:

• Gangster Hangouts: Explore the nooks and crannies of neighborhoods like River North and Lincoln Park where the Mafia spun its web.
• Biograph Theater: The infamous site where public enemy number one, John Dillinger, was killed after being betrayed.
• Holy Name Cathedral: Witness the lingering bullet holes from a bloody Prohibition-era mob hit.
• Historic Crime Scenes: Hear the macabre stories of the St. Valentine's Day Massacre and the traps set by the serial killer H. H. Holmes.
• Courthouse & Restaurants: Pass by the Cook County Criminal Courthouse and learn the hidden mob stories behind iconic restaurants.

🗓️ Tour Options: Day or Night?

This tour offers two distinct experiences, both starting and ending at the same location and including bus transport with an English-speaking guide.

• Day Tour: 1h 30m to 2-hour tour focusing on the historic sites and stories. (Operates daily at 10 am, 12 pm, 2 pm, and 4 pm).
• Night Tour: A longer, 2 to 2.5-hour tour that follows the same itinerary but spends more time at each location, complete with a "delicious" surprise stop revealed along the way. (Operates Mondays, Thursdays, and Fridays at 7:30 pm).

ℹ️ Practical Details:

• Duration: 1h 30m - 2h 30m, depending on the option chosen.
• Meeting Point: 163 E Pearson St.
• Accessibility: Not wheelchair accessible.
• Pets: Not permitted.
• Cancellation: Free cancellation up to 24 hours before the activity starts.

🗺️ Looking for Other Chicago Experiences?

Beyond walking tours, Chicago offers river cruises, bus tours, food experiences, and visits to famous museums. If you'd like a different experience, a private tour, or want to explore all available activities, check out more options below.