Chicago’s Notorious Gangster Hangouts

During the prohibition era, some of the country’s most notorious gangsters ran this city. Here are some hangouts you can still get a sip and a bite at today.

Butch McGuire’s

via Flickr user Shutter Runner

via Flickr user Shutter Runner

Open for over 50 years, this historic spot used to be a speakeasy and a stripclub, but it’s now (somewhat ironically) one of the most notorious bars for single people to come and mingle. Apparently over 7,500 married couples met here. Even the hardest of the prohibition gangsters fell in love, were married, and had kids.

20 W Division St
(312) 787-4318
www.butchmcguires.com

Fox’s Restaurant & Pub

via Flickr user Thomas Hawk

via Flickr user Thomas Hawk

This place has what many people call the best pizza in the city, and the rest of the menu is as excellent as it is eclectic. The place is very reputable, and is a local chain adored for dine-in, delivery, catering, and private parties. The kicker? This location used to be a deli owned by—we’re not kidding—Al Capone’s sister.

9956 S Western Ave
(773) 239-3212
www.foxsrestaurant.com

Green Mill Cocktail Lounge

Al Capone's Booth via Flickr user Tom Gill

via Flickr user Tom Gill

We saved this one for last because anyone who knows anything about Chicago’s prohibition era history knows that the Green Mill was a hotspot. This place is like stepping back in time, with a chic interior, overstuffed seats, an extensive selection of specialty cocktails, and live jazz music. Al Capone used to frequent this place, and his go-to booth is still there (pictured above).

4802 N Broadway St
(773) 878-5552
www.greenmilljazz.com

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