Chicago’s Speakeasies

If figuring out how to get into a speakeasy isn’t your cup of bathtub gin, try Amy Bizzarri’s Chicago Cocktail Adventure (Part 1 and Part 2). Or you can combine drinking with learning about Haunted Chicago on Leentje De Leeuw’s Spirits of the Windy City Adventure.

By Dave Lifton (@daveeatschicago)

The word “speakeasy” evokes images of Roaring Twenties wonder, of underground bars accessible by a password selling home-distilled booze as someone kept an eye out for the fuzz. Chicago, of course, became synonymous with bootlegging during Prohibition, and there are still a handful of former speakeasies still in existence as legitimate bars.

Over the past decade-and-a-half or so, many bar owners have capitalized on the allure of speakeasies by putting secret rooms into their establishments. These are more likely to have fancy cocktails rather than the homemade rotgut of a century ago and there’s little chance of a raid, but the feeling of drinking in secret remains. Below, see our favorites of the old and new.

Original Speakeasies

Chicago’s oldest bar, Marge’s Still, started life in 1885 as a saloon/barber shop in Old Town called “Victor Caruso’s Soft Drinks.” During Prohibition, the still-visible side staircase gained visitors entry into the speakeasy. Marge Landeck became the first woman in Chicago to possess a liquor license when she bought the bar in 1957, and it was named in her honor in 2004. Now a gastro pub, the original wooden bar remains, but the gin distilled on the second-floor bathtub has been replaced by craft beer and swanky cocktails.

Although many places in Chicago claim to have a connection to Al Capone, the reality is that very few remain, and most have undergone many changes since his time. The Green Mill in Uptown is an exception and a safe space on the North Side for the South Sider (it was owned by one of his henchmen, “Machine Gun” Jack McGurn). It’s now one of the best jazz clubs in town, and also the birthplace of the poetry slam. If you’re lucky, you may be seated in Scarface’s old booth, but don’t inquire about the tunnels that he would use to escape when the heat was on.

Ric Addy & The Green Mill

If Capone’s history at the Green Mill is somewhat downplayed, it’s emphasized at the Exchequer. Walk into the Loop bar and you’ll see news stories and photos of him and other infamous Chicago underworld figures on the walls. It opened in the 1920s as the 226 Club, a restaurant/speakeasy with a brothel on the second floor, and Capone as an off-the-record owner.  

The sign outside Simon’s Tavern in Andersonville says it’s been around since 1934, but that’s not entirely true. During Prohibition, grocery store owner Simon Lundberg received a “proposal” from bootleggers to sell whiskey with his coffee. By 1926, he bought a new place on Clark St., opened the N.N. Club as a speakeasy in the basement, and came above ground after the repeal. These days, Simon’s is loved for its Art Deco decor, live music Wednesdays and Sundays, and its glogg, a hot, spiced wine sold at Christmas time.

Modern Speakeasies

Two former speakeasies have built hidden bars within their existing spaces, both of which have considerably sleeker vibes than the main rooms. In late 2024, the aforementioned Exchequer debuted Club X, which is accessible from an easy-to-miss door in the back dining room. The Drifter is found below River North’s Green Door Tavern, a building constructed in 1872. The cocktail menu changes nightly, with the staff choosing from a list of more than 100 drinks and prints its selections on custom-made tarot cards.

Jazz Age splendor is intended at Gatsby, which can only be accessed by solving a puzzle to find the secret entrance and giving a password. The Lincoln Park bar is decked out like a Victorian-era study, complete with bookcases and paintings, and the cocktails are named after passages from F. Scott Fitzgerald’s The Great Gatsby, including the Voice Full of Money and Flowers for Daisy.

It’s very easy to walk past The Violet Hour in Wicker Park, particularly at night. There’s no signage and the door is obscured by a mural. Inside is one of the city’s most acclaimed mixology bars, with a James Beard Award-winning cocktail menu that changes seasonally, and three rooms, each that provide a distinct ambience.

From the outside, Dorian’s looks like a typical record store with obscure vinyl in the windows and racks. But beyond the “Listening Booth” is a swanky lounge where the drinks can have ingredients like ancho chile, blackberry-infused Averna, or hopped grapefruit bitters. The music theme is continued, with jazz, funk, soul, or house music almost every night.

Behind Moon Palace Express, a stalwart takeout spot in Chinatown, is Nine Bar. There, you can find innovative cocktails with Asian flavors and classic American drinks with an impressive assortment of Asian spirits. But although there’s a Mai Tai on the menu, do not expect tiki bar vibes.

For more information on these and other secret bars, visit chicagospeakeasies.com.