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Chicago isn’t only one of the most entertaining cities of the world, it’s one of the most historic. Now it might not have the roots that many cities on the East Coast do—Boston, Philly or New York—but its history is colorful and important.

Best known for its wilder years of prohibition, this is a great city to take a historic pub crawl in. And if you’re going to make a historic pub crawl in Chicago, you’ve got to hit the speakeasies. Here are three of the best historic speakeasies in all of Chicago.

3. The Green Door Tavern

img 0131Though the building dates from 1870 the real history started in 1921 when an Italian restaurant by the name of The Heron Orleans replaced the grocery store and when the owner passed it on to his kids they did like every entrepreneur of the time and opened a speak-easy downstairs. 

At some point in time, it is unclear if it was during prohibition or after, the name was changed to The Green Door Tavern, named after its green door and entrance.  At the time and during most of prohibition a green door represented a speak-easy and a place one could find alcohol and other illegal forms of entertainment such as gambling. 


The speak-easy’s alcohol was supplied by the North Side Gang and more specifically Irish-American mobster and bootlegger Dean O’Banion.    This would have made the Green Door and its suppliers an enemy of the more famous and more notorious Al Capone.

It survives today with excellent cocktails (try the Moscow Mule or the French 75), great food (trust us, go with the corned beef sandwich), and pristine speakeasy downstairs.

Watch the documentary on the Green Door Tavern here.

2. Simon’s Tavern

img 0336Opened in the mid-1920’s as a café by Swedish immigrant Simon Sumberg the place became a speakeasy soon thereafter. Supplied by Al Capone’s men, Simon sold whiskey out of the tiny room downstairs, now used as an office by the Owner, Scott.

For a nickel Scott will take you downstairs and give you the whole history. Bottom line, excellent speakeasy in a really interesting area of the city.

While you’re there definitely wet your whistle with some of the house drinks—this is a Swedish bar after all. Try the Aquavit, a Scandinavian liquor like a vodka infused with anise seed and caraway.

Or, even better, if you go during the winter try the glogg, a traditional Scandinavian spiced wine they make just for the holidays.

Watch the documentary of Simon's Tavern here.

1. The Green Mill

img 0450Opened to be America’s version of Moulin Rouge in Paris (France, not Texas), the Green Mill took up practically a whole city block. It had dancing girls, fountains and tons of excess. Unfortunately prohibition put an end to all that.

When prohibition did pass they reduced the size to the current lounge and continued serving. The place was partially owned by one of Capone’s mobsters, “Machine Gun” Jack McGurn (a rotten human being if there ever was one).

Capone himself used to frequent the place.

Today it is one of the best jazz bars in the country. Get here early and order a traditional cocktail then relax and soak in the history.

Watch a documentary of the Green Mill here.


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