The Green Mill

The Green Mill: Our most recommended tours and activities

Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

1. 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.

Chicago: Private 3-Hour Al Capone Gangster Tour

2. 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.

Chicago: Private Guided Tour of Chicago Suburbs Movie Sites

3. Chicago: Private Guided Tour of Chicago Suburbs Movie Sites

Cruise through the streets of Chicago's suburbs on a private guided tour of the city's most famous filming locations. Get the behind-the-scenes scoop about your favorite movies and visit 25 iconic movie sites. Meet your guide, a local actor, and set out to explore the Windy City. See Cameron's house from Ferris Bueller's Day Off, take in the famous football field from The Breakfast Club, visit the site of the record store from High Fidelity, and much more. Throughout the tour, your guide will offer interesting facts about the movies filmed on location in Chicago. Whether you’re a diehard John Hughes fan, or you're into classic mobster movies, this city has much to offer any movie buff. And there's no need to worry about the weather as you'll travel through the city in a comfortable air-conditioned or heated car, depending on the time of year. Your tour of Chicago's famous filming locations comes to an end at Revolution Brewery. Feel free to hang out here after the tour ends and grab a beer (cost not included).

  • Private tours
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Other Sightseeing Options in The Green Mill

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What people are saying about The Green Mill

Overall rating

5.0 / 5

based on 3 reviews

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!