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Chicago's Best Old-Timey Bars

By Jenny Schooley

Old-school establishments are some of my favorite city nightspots. While I'm no stranger to many of the newer bars lining Chicago streets, it's the atmosphere of the city's older watering holes that piques my interest. John Dillinger, Public Enemy No. 1, used to hang out at John Barleycorn Lincoln Park. He even bought the house around the corner after robbing a bank. Whether it's bank-robbing pastimes or the random pre-WW2 decorations hanging from the walls - Chicago's storied bars are mainstays in the community. So before you belly up to the local bar, take a peek at what's on tap at several longstanding Chicago bars.

3/29 Nightlife & Music Glascotts

Hours: Mon – Fri 10 a.m. – 2 a.m.; Sat 11 a.m. – 3 a.m.; Sun 11 a.m. – 2 a.m.

This neighborhood bar sits at the bottom of a three-flat brick building at Halsted and Webster. The Groggery originally opened in 1937 as "Larry's Tavern," named after the original owner, Lawrence Glascott. According to the bar's history, the Glascott's had been in the saloon business since the late 1800s. Today, Glascott's delivers generous pours and quick pints, but the building was previously a meat market and a speakeasy during prohibition. Stop by and find a bar full of Irish cheer and a jukebox turning out tunes.

Twin Anchors
Twin Anchors. (credit:

Hours: Mon – Thurs 5 p.m. – 11 p.m.; Fri 5 p.m. – 12 a.m.; Sat 12 p.m. – 12 a.m.; Sun 12 p.m. – 10:30 p.m.

Although it's touted as having the best baby back ribs in the city, Twin Anchors is a timeworn (75 plus years) establishment. Dating back to the 1880s, Twin Anchors was originally the home of a butcher and a police officer. It operated as a saloon until Prohibition, when the space turned into a speakeasy, advertising only "soft-drinks." In 1932, Bob Walters and Herb Eldean, members of the Chicago Yacht Club, opened the bar, applying the nautical vibe. Through the years, celebrities such as Frank Sinatra, Conan O'Brien, and even Batman's DA Harvey Dent have stopped in for a drink. While it's changed ownership, Twin Anchors remains a Chicago cornerstone.

3/29 Nightlife & Music Glasses of Whisky

Hours: Mon – Fri 11 a.m. – 2 a.m.; Sat 4 p.m. – 3 a.m.

Established in 1881 and acknowledged to be the oldest bar in Chicago, this pub-restaurant sits across the street from the 11th Ward Democratic headquarters and just a few blocks from the White Sox stadium. Schaller's serves a lively crowd of sports enthusiasts and regulars. Picture an old-time dive with cold brews.

3/29 Nightlife & Music Green Door Tavern

The Green Door Tavern dates back to 1921. The River North building once served as a grocery store, restaurant, and speakeasy. Antiques and collectibles trim the bar, exuding a classic, old-time Chicago feel. The name "The Green Door" stems from the prohibition custom of a green door on a restaurant indicating the presence of a speakeasy. The original 137-year-old green front door is still standing and ready to welcome visitors.

3/29 Nightlife & Music Burnwood Tap

A family owned and run bar since 1933, Burwood Tap is nestled in the Lincoln Park neighborhood. Find a pool table, free popcorn, and a feel-good setting. Décor comes in all shapes and sizes—model airplanes, violins, even golf clubs. With a nod to modern times, Burwood Tap is a great place to go after work or on the weekend and catch the Cubs game on one of its many HD flatscreen TV's.

Jenny Schooley is a Chicago-based writer and editor. She currently works as a communications analyst for a financial corporation.


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