Things to do in
Old Town Triangle

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Old Town Triangle: Our most recommended tours and activities

Chicago: 90-Minute Mob and Crime Bus Tour

1. Chicago: 90-Minute Mob and Crime Bus Tour

Experience Chicago’s underworld of criminals and gangsters on a luxury 90-minute bus tour. Find out how some of the world’s most famous criminals, mobsters, and gangsters conned their way through the city. Ride comfortably in luxury, on a climate-controlled bus, as you see famous Chicago crime scenes that range from the 19th century through modern times. Unlike Chicago walking tours, this Mob and Crime Tour isn’t affected by the Windy City weather. Learn from a local expert tour guide giving interactive live commentary about Al Capone, the Untouchables, the Chicago Mob, John Dillinger, Terrible Tommy O'Connor, H. H. Holmes, the Chicago Black Sox, Leopold and Loeb, bank heists, Cap George Streeter, and more. Grab your camera for a drive-by shooting of the historic criminal courthouse, a Chicago architectural landmark where some of Chicago's most notorious cases were tried. You'll also view historic video footage, receive an informative pamphlet with photos, and can even take part in a crime quiz. Stake out crime scenes like the Biograph Theatre, Holy Name Cathedral, Clark Street Bridge, and other Chicago landmarks. See the site of the St. Valentine's Day Massacre, one of Chicago's most notorious murder scenes. Get off the bus and walk the path that notorious Chicago gangsters John Dillinger and Hymie Weiss followed just before their deaths. Travel into the criminal past of Chicago's River North, Gold Coast, Lincoln Park, Old Town, Loop, and Magnificent Mile neighborhoods.

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Chicago Crimes Night Tour

2. Chicago Crimes Night Tour

Uncover how some of the world’s most famous criminals, mobsters, and gangsters conned their way through the Windy City. Ride in luxury on a climate-controlled bus, as you explore famous Chicago crime scenes ranging from the 19th century through to modern times. Learn about Al Capone, the Untouchables, the Chicago Mob, John Dillinger, The Lady in Red, Captain George Streeter, Frank "The Enforcer" Nitti, Bugs Moran, Johnny Torrio and more. Grab your camera for a drive-by shooting of historic and architectural landmarks, and stake out crime scenes like the Biograph Theatre, Holy Name Cathedral and St. Valentine's Day Massacre, one of Chicago's most notorious murder sites. Walk the path that notorious Chicago gangsters John Dillinger and Hymie Weiss followed just before their deaths. Travel into the criminal past of Chicago's River North, Gold Coast, Lincoln Park, Old Town, Loop, and Magnificent Mile neighborhoods.

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Other Sightseeing Options in Old Town Triangle

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What people are saying about Old Town Triangle

Overall rating

4.3 / 5

based on 399 reviews

John, guide, and Wayne, driver, were both excellent at their jobs. Chicago is a beautiful city and your 40+ person bus was clean and comfortable ( only 15 participants). We saw the outside of the theater where Dillinger spent his last night, the alley where he was shot, and the Harry Caray Restaurant where there was a lot of historical news articles and photographs to look at. Everything else was “the building used to be here where... “ or “see that McDonalds, that used to be...” Again, John did an excellent job painting the historical background and telling the stories of the north side and south side gangs. I just wished that Chicago had the foresight to keep/rebuild/remodel some of the 1920s/1930s historical places that defined that era.

It just so happened that 1 of the days I was in town called for rain & this was perfect. There are 2 stops where you can get off the bus & we were able to do both of those despite a few rain drops. Leah was super knowledgeable on all areas of Chicago crime. I felt like the whole tour flowed very well from start to finish.

John was our guide and he was so much fun to have leading us through the whole thing! He’s very knowledgeable and made the whole experience fun & interesting! Highly recommend trying this out!

Was a terrific way to get out and see a little bit of the city and learn about some gangsters.

Our guide was great and very informative. His dad jokes were pretty on point too.