2 3-Hour Experiences in Chicago Worth Booking

1.Private 3-Hour Al Capone Gangster Tour

★★★★★★★★★★4.8 · 9 reviews · 3 hours Our pick

Spend three hours with a gangster historian and private group of up to five, visiting Chicago crime sites, old speakeasies, historic hotels, the Green Mill, and Dillinger’s assassination site. Guides speak English or Chinese, and Conor is one guide praised for an engaging, detailed tour.

“I enjoyed that we had a say in what areas we wanted to focus on. We chose to do more of the Al Capone items as he was possibly a frequent visitor of a bar our family once owned in the area.”

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2.3-Hour Private Speakeasy Cocktail VIP Tour

★★★★★★★★★★5.0 · 7 reviews · 3 hours Top rated

Spend three hours with a private guide such as Alan or Kai, visiting three or four working Chicago speakeasies by luxury vehicle. Hear Prohibition and gangster stories, enter through secret passages, and buy period-style cocktails at each stop. Hotel pickup and drop-off within Chicago are included.

“Alan, our host, was knowledgeable, kind and funny. He took us to great spots and made everything so fun. It was a huge hit with my group.”

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