Top 2 3-Hour Experiences in Chicago

1.Private 3-Hour Al Capone Gangster Tour

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

Ride with a historian guide and chauffeur to Chicago mob-era sites, including the St. Valentine’s Day Massacre location, a theater tied to John Dillinger, and Al Capone’s booth at the Green Mill. Your private group of up to five gets hotel pickup within city limits and luxury transportation. Guides have included Conor, though your assigned guide may differ.

“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.”

Check availability →Read our full review

2.3-Hour Private Speakeasy Cocktail VIP Tour

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

Spend three hours with a private guide visiting three or four working Chicago speakeasies, some preserved in their original condition. Enter by secret passages, hear stories of bootlegging and racketeering, and get cocktail recommendations inspired by the era. Alan and Kai have led the tour, though your guide may differ. Luxury transport and city-limit hotel pickup are included; drinks cost extra.

“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.”

Check availability →Read our full review