Take a Trip Back in Time at These Historic Chicago Bars

Chicago, bars, oldest bars in chicago, chicago prohibition bars, chicago speakeasies, chicago history
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Chicago has a rich and turbulent drinking history. From pre-prohibition, to prohibition, or post-prohibition, the city has long been home of many amazing bars. Some of the oldest of them are still standing today, decades after they first opened their doors.

Whether you’re a history buff or just want to grab a good drink, keep scrolling to learn about a few of the oldest bars in Chicago.

Marge’s Still

If you ever find yourself at a trivia night, and you’re asked to identify the oldest bar in Chicago, your answer would be Marge’s Still. It has had that title since 2017 after Shaller’s Pump, the former titleholder, closed down.

Once upon a time, it was an old school saloon in Chicago’s historic Old Town Triangle neighborhood. It had it all: an antique wooden bar that still stands today, a bathtub where they brewed gin, and a secret entrance. Today, it’s a classic neighborhood bar that serves up good drinks and bar eats.

The Green Mill

The Green Mill is the most popular bar on this list and a throwback to the prohibition era.

This jazz bar opened in 1910 as a part of the Green Mill Gardens. According to Dave Jemilo, Green Mill’s owner since 1986, the amenities included the lounge, a ballroom upstairs, an adjoining restaurant, and outdoor gardens.

Al Capone frequented this place. As a result, liquor flowed during prohibition. There was even an underground tunnel behind the bar used to transport alcohol back then. The booze still flows inside The Green Mill today, but it enters the bar legally.

The Berghoff

Herman Berghoff immigrated from Germany to Indiana and started brewing Berghoff’s Beer with his brothers. Berghoff went to Chicago in 1893 to sell his beer at the 1893 Columbian Exposition, Chicago’s World’s Fair.

At the fair’s end, Herman opened the Berghoff Bar, selling beer for just five cents. Berghoff’s business plan had to be revised when the 18th Amendment, Prohibition, passed in 1920. He then opened up a restaurant serving traditional German food.
When word spread that prohibition was about to be repealed, Berghoff camped outside of City Hall to get the city’s first liquor license, which they still proudly display inside their bar today.

Today, The Berghoff Bar and The Berghoff Restaurant are still run by the Berghoff family, making it the city’s longest-running and family-owned eatery.

Twin Anchors

Prohibition led to the conversion of this Old Town establishment into a speakeasy called Tante Lee-Soft Drinks. There were boarded-up windows on the front of the building to conceal the illegal activity inside.

Later a favorite hangout of Frank Sinatra, this infamous rib joint was also featured in films ranging from The Dark Knight Returns to Me. The Chicago Prohibition Tours company claims that one of Sinatra’s bodyguards would stand near the payphone inside to prevent anyone from announcing his presence.

Ownership changed after prohibition ended, and the establishment evolved into the nautical establishment that it is today, but the bar’s classic jukebox still features Sinatra songs.

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