Prohibition still captivates the public’s imagination more than 100 years later. This is especially true in Chicago thanks to numerous depictions in popular culture in the ensuing decades. Remnants of those days still exist at the old Chicago bars listed below. Many have a history as speakeasies, while others evoke Roaring Twenties glamor.
Green Mill Cocktail Lounge
Nothing Fancy: Every night, Uptown’s Green Mill features some of the city’s best jazz, ranging from traditional to modern, with a cover charge typically between $10 and $20. It’s defiantly old-school: cash only, with no reservations, dress codes or fancy drinks. That extends right down to the decor and the vintage jukebox that plays before and between sets.
Notorious Past: Opened in 1914, Al Capone hung out at the Green Mill during Prohibition. His favorite booth is still there, and you can sit there, if you’re lucky.
The Coq D’Or
Elegance Exemplified: Don’t expect speakeasy vibes at the Drake Hotel’s Coq D’Or. Instead, it greets guests with luxurious reds and woods, and jazz on weekend nights. Unwind after a day on the Magnificent Mile with an Executive Pour martini (“a martini with a side of martini”) or a cocktail made with its exclusive rye made by local craft distillers FEW Spirits.
Historically Significant: The Coq D’or opened the day after Prohibition’s repeal and has Chicago’s second post-Prohibition liquor license. The first was The Berghoff.
Lockwood Lobby Bar
Classic Splendor: Located in the Palmer House Hilton, the Lockwood Lobby Bar surrounds guests with Roaring Twenties luxury. Sit at the bar or a table and have a drink while staring at the ceiling frescoes depicting Greek mythology or the stunning Tiffany Winged Angel candelabras.
What to Order: The brownie was invented at the Palmer House as a snack during the 1893 World’s Fair. The confection inspired an old-fashioned, comprised of rye, Frangelico and creme de cacao, with a brownie garnish).
Simon’s Tavern
Locals’ Favorite: A classic neighborhood bar that opened in 1934 shortly after Prohibition’s repeal, the cash-only Simon’s Tavern in Andersonville is unfussy and welcoming. During the winter, go with the glögg, a hot mulled wine served with a butter cookie. If you dare, get a shot of Malört, a notoriously bitter Swedish liqueur that polarizes Chicagoans. Catch live blues, jazz or rock every Sunday and Wednesday.
Joyously Kitschy: See Simons’ Swedish roots in the neon sign of a fish with a Viking helmet holding a martini that greets visitors. In other words, a pickled herring.
Green Door Tavern
Prohibition-Era Speakeasy: Housed in one of the few wooden structures built immediately after the Great Chicago Fire, River North’s Green Door Tavern opened in 1921, during Prohibition, as a grocery store with a speakeasy in the basement. The massive collection of Americana lining the walls is as impressive as the large whiskey selection. That basement speakeasy is now The Drifter, a chic cocktail lounge.
Championship Pedigree: Chicago Bulls legend Dennis Rodman made it his regular stop for a pre-game meal on Tuesdays.
Marge’s Still
Historical: Since 1885, a tavern has stood at the Old Town corner now occupied by Marge’s Still, making it the oldest bar in Chicago. During Prohibition, the side staircase was the entrance. The original wooden bar remains, but you can now get local craft beer and traditional cocktails instead of the gin distilled in the second floor bathtub.
Honoring the Past: Marge’s was founded as a combination barber shop and saloon called Victor Caruso’s Soft Drinks. The tavern is now named in honor of Marge Landeck, who owned it from 1957-2001.
Zebra Lounge
Gold Coast Institution: Neatly tucked inside an apartment building, the intimate Zebra Lounge opened in 1929. Every night, pianists keep the party going, with a songbook that ranges from standards to contemporary hits. Grab a martini, admire the zebra-themed interior and sing along.
Pro Tip: Although the music starts at 8:30 nightly, get there early, because reservations aren’t accepted.
