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Harry Caray's Italian Steakhouse

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Harry Caray's Italian Steakhouse: 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: 3-Hour Private Speakeasy Cocktail VIP Tour

2. Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

Spend an evening visiting the Chicago speakeasies that have been open since the Prohibition Era in the 1920s, many preserved in their original conditions. With your own private group, enter by way of secret entrances and enjoy the same cocktails ordered by infamous Chicago gangsters and bank robbers at these venues nearly a century ago. Relive the glamor of the 1920s while listening to stories of the rampant racketeering and bootlegging of the era.   Alcohol is available for purchase at the three to four different speakeasy stops. Your private tour guide will make Prohibition Era drink recommendations and tell you the stories behind them. Travel around with your young, professional guide and be chauffeured in luxury transportation, ranging from a luxury SUV to a full-sized luxury motor coach.

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Chicago: Private 3-Hour Al Capone Gangster Tour

3. Chicago: Private 3-Hour Al Capone Gangster Tour

Experience amazing stories of true crime coming to life on this three-hour private tour. Visit many of the old venues where gangsters used to operate, including old speakeasies and historic hotels. Your expert historian guide will accompany you and your private group in luxury accommodation to historically significant locations in the city. View crime scenes immortalized in vintage news footage, the theater where the law caught up with Dillinger, and the restaurant where the North Side Gang riddled Al Capone’s motorcade with rounds from their Tommy guns. See the site of the infamous St. Valentine’s Day Massacre, and sit in Al Capone’s booth at the Green Mill. Finally, visit the location where Public Enemy #1 John Dillinger was assassinated by the FBI.

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Other Sightseeing Options in Harry Caray's Italian Steakhouse

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What people are saying about Harry Caray's Italian Steakhouse

Overall rating

4.3 / 5

based on 358 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.

Kai was an excellent guide for our activity last night. She had so much knowledge of Chicago history and when we requested more of history/ gangster knowledge vs just the speak easy stops, she made a significant pivot to make our activity specific to our requests. Would highly recommend this tour and Kai!

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.