All eight of these watering holes do Chicago’s venerable drinking history proud
Southport Lanes has a bit of a naughty past. After being sold by Schlitz Brewery, the bar had to resort to offering prostitution on the menu to be able to afford to stay open and serve alcohol. Because prostitution was, and still is, illegal in Chicago, the owner had murals painted on the walls depicting nymphs to subtly advertise what went on upstairs. These murals can still be seen today above the bowling pins.
When that period ended, Southport Lanes acquired new ownership and remained a popular tavern. What makes this joint so unique and old fashioned is that the pins are still handset by pinboys in the back. Be sure to tip them by stuffing a bill into a bowling ball and, for their sake, don’t bowl if you see legs (as the sign says). This is a downright cool hangout spot, with bowling, billiards, upscale bar food and inexpensive drinks.
The Green Mill
The Green Mill has been around since 1907, but back in those days, it was more of a roadhouse spanning the entire block than just a cocktail lounge. It was a favorite hangout joint for Al Capone and Frank Sinatra. Charlie Chaplin himself would also come in for a drink after working at the Essanay Studios on Argyle Street. During Prohibition, the bar served as a gangster hangout and speakeasy. The door with a slit that would be opened for the ‘secret password’ has been replaced with glass doors, but one can still feel the classic 1920s-30s bar style, with some cool historic features. Behind the bar, there is a trap door that leads to the basement and a series of tunnels that were previously used to illegally deliver alcohol.
Located right in the heart of the Loop, the Berghoff is over a century old and is definitely one of the most historically rich places in Chicago. The interior transports guests to a different time, with black and white pictures of old Chicago, stunning original woodwork, and the famous stand-up bar.
Originally, Berghoff’s was solely a bar, but later expanded to serve food to stay afloat during Prohibition. From 1920-1933, Herman Berghoff gained notoriety for his ‘near-beer’ and Bergo soda pop. Despite not running a speakeasy, the establishment was very successful. However, in 1933, when Prohibition ended, he was the first one in Chicago—and possibly the Midwest—to obtain a liquor license. The original document is still on display at the restaurant, and makes for a unique photo-op.
The Green Door Tavern
Immediately following the Great Chicago Fire of 1871, James McCole built this two-story structure that was originally a grocery store. It is one of the few remaining buildings built prior to the fire code prohibiting the construction of wooden commercial buildings in the Business District. Once the building settled, it began to lean. It has been that way for over 100 years and the slanted floor is still noticeable. The name ‘Green Door Tavern’ came from the restaurant’s green door, indicating it was a speakeasy during Prohibition.
The menu may have changed over the years, but this laidback restaurant is the perfect hangout spot for watching the Cubs, Bulls, Bears, Hawks & Sox, and feeling like you’re back in the ‘20s with the friendly, down-to-earth staff and old fashioned memorabilia on the walls.
This 125-year old Bridgeport establishment represents classic American traditions – baseball and politics. It is the oldest tavern in Chicago and served as both a “second office” for five of Chicago’s mayors, and a haven for Sox fans, as well as a speakeasy in the Roaring ‘20s. The interior is painted black & white – Sox colors, and is the perfect spot to have dinner before or after cheering on your favorite baseball team.
The Cove Lounge
It doesn’t get older fashioned than this. Step inside the tall, single story structure with the sign out front that reads “Cocktail Lounge”. And it’s just that – there is no food served here, though you may be able to snag a package of peanuts. This low-lit, nautical themed bar is rich in historical features, with a mahogany bar that dates back to Prohibition-era. Up until 1967, jazz piano used to be played in the back room until new ownership took over and cut that out. It’s said that the jazz music inspired University of Chicago dropout Kurt Vonnegut to have written Player Piano, his first published novel.
John Barleycorn Memorial Pub
This Lincoln Park location has been open since 1890 and during Prohibition, the outside was boarded up to appear vacant, while inside, it was a full-blown speakeasy. John Dillinger, Public enemy No.1, used to hang out here. He often bought the house a round with his money obtained after robbing banks. A fun fact: Dillinger was eventually gunned down in an alley just a few blocks north of the Pub.
Located on Historic Printer’s row in the South Loop, Kasey’s Tavern has one of Chicago’s oldest liquor licenses and occupies the first building built after the Great Chicago Fire. This warm and inviting bar atmosphere offers over 150 different types of beers.
- Dawn Trottier