The 3 Most Legendary Bars in Chicago


Ready for a drink and some vintage chit-chat? You can enjoy a brew in one of Chicago’s historic pubs or taverns and soak up the ambiance of days gone past. Come for the drinks; stay for the atmosphere.

These establishments have survived prohibition and the ups and downs of American life over many decades.

Twin Anchors

Opened in 1932, the Twin Anchors was a Prohibition-era speakeasy called Tante Lee Soft Drinks, serving alcoholic beverages to the deprived.

This place was a favourite of Frank Sinatra. To prevent word of his presence from spreading, Ol’ Blue Eyes would station one of his bodyguards at the payphone.

Browse through their website’s collection of memories compiled by nostalgic patrons to see how this place contributed to Chicago’s history.

Green Mill

Originally called Pop Morse’s Road House, this cocktail lounge changed its name to Green Mill because it was to be America’s answer to the Moulin Rouge (“Red Mill”) in Paris.

When the Mill opened in 1912, it had much in common with the Moulin Rouge: dancing girls, champagne fountains and expansive ballrooms. Prohibition led to the establishment downsizing to its contemporary lounge. During the early 1930s, it was a speakeasy co-owned by one of Al Capone’s notorious enforcers, “Machine Gun” Jack McGurn.

The Green Mill remains a great place to experience Chicago’s live jazz and poetry scene.

Shinnick’s Pub

The Shinnick’s story begins with the repeal of prohibition.

George Sr. and Mary (Healy) Shinnick acquired the Union Avenue bar in 1938. In 1966, ownership passed to George Jr. and his wife Celine, who raised nine children in the borough of Bridgeport and passed on their family’s traditions and values. That is all a family-run business needs to succeed.

To this day, the Shinnick kids own and operate the bar. The Shinnick family has poured beer for Bridgeporters for three generations. Shinnick’s pub is part of the fabric that keeps the city together, earning the nickname “Little City Hall.”.

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