With the recent influx of retro-style cocktail bars, taverns and restaurants in Chicago, it's increasingly evident that old is new again. But isn't that the general cycle of all things awesome?

Start in the 1920s and make your way to the 70s with this list:

The Drifter

When it comes to historic, classic Chicago joints, this place is the bees knees! Built shortly after the Great Chicago Fire, The Green Door Tavern (678 N. Orleans St.) maintains its historic roots. Its name derives from a 1920s code that indicated there was a speakeasy in the establishment.

Now with The Drifter (676 N. Orleans St.), a newer cocktail bar located in the basement of The Green Door Tavern, its green-colored door serves its purpose even today. The re-envisioned space, most recently used for private parties, is every bit a speakeasy brimming with history, with a separate entrance and a secret door that was used during Prohibition to get booze to its patrons. Complete with turn-of-the-20th-century memorabilia, including a phone booth and circus décor, The Drifter also offers a unique twist with its cocktail program. Each drink selection is printed on a menu of Tarot Cards, and each night presents a different set of cards — that should keep you guessing!

The Franklin Room

Carrying on the speakeasy tradition — or trend — is The Franklin Room (675 N. Franklin St.) in River North. Located in the building's lower level, this modern-day tavern pays homage to secret bars of Chicago's past. Built-in wall cabinets throughout the space showcase a large collection of spirits, and whiskey specifically. Anyone particularly taken by a rare bottle can purchase it right there for immediate gratification through its Bottle Keep program and also opt to store that special bottle in a secure cabinet for future sipping.

California Clipper

Sometimes maintaining that aged-yet-not-tattered feel simply involves a little bit of a facelift. Since restaurateur Brendan Sodikoff took ownership of California Clipper (1002 N. California Ave.), a historic neighborhood cocktail lounge in Humboldt Park, the place has only grown in popularity. In keeping the Art Deco accents, red-lit atmosphere and jukebox tunes, the revamp of California Clipper is a true old-is-new-again transformation. Be sure to check out the 70-page drink menu and live music calendar.


Travel down memory lane at this sexy West Loop supper club inspired by classic red sauce joints of the 1950s. At Formento's (925 W. Randolph St.), American-Italian cuisine gets the spotlight, from homemade bucatini and giardiniera to grandma's recipe for meatballs, and the hospitality is second to none. Big red booths and white tablecloths are reminiscent of that Old World charm, but don't forget, this is Restaurant Row, so dress chic so you can sip on your vino (the wine menu is both massive and masterful) at the front bar in style.

The Duck Inn

A Mid-Century Modern aesthetic meets New American cuisine at The Duck Inn (2701 S. Eleanor St.). Housed in a pre-Prohibition era tavern, this Bridgeport gem is on the river's industrial edge but beckons diners with dishes from Michelin-starred chef Kevin Hickey. The neighborhood native has strong connections to the space and its tight-knit community, and he infuses that history throughout.

Some examples: The building is circa 1914 and his restaurant opened in 2014 so the halfway point of 1964 was an inspiration for decor... funky light fixtures, vinyl booths, vintage glasses. Bar bites play off an old photograph of the original Duck Inn, a long-gone family-owned eatery, with its grass-fed beef hamburger sandwich (though no longer 5 cents) and duck confit/foie gras tamale. Channel the swingin' 60s while you sit in the cozy front bar (BYO Vinyl Night is on Mondays mind you), or step into the dining room for the signature dish, a whole rotisserie duck.

Dove's Luncheonette

Playing the soulful sounds of the 60s and 70s, Dove's Luncheonette (1545 N. Damen Ave.) is a revival of the classic American diner experience. If the jukebox doesn't scream old-school, the wood panels along the wall, the big brown mugs, swiveling bar stools and classic framed photos adorning the wall will surely remind you of the decades-old neighborhood eateries that welcomed you with hearty food and hot coffee from the wee hours of the morning to the wee hours of the night. While Dove's is not open 24 hours, the "Southern-inspired Mexican menu" and extensive tequila/mezcal lists invite you to drop in early, noon and night.


Related Listings

The Duck Inn
2701 S. Eleanor St.
Chicago, IL 60608
(312) 943-7600

925 W. Randolph St.
Chicago, IL 60607
(773) 862-5555

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