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Easy Does It

Easy Does It is a low-key wine bar that also serves cocktails in Logan Square.

Six destination cocktail bars in Chicago

There was a collective Chicago lament this fall when the soaring, glass-paneled Signature Room atop the John Hancock closed abruptly. Just like that, it was an end to the martini in the sky.

Even if you rarely trekked up to the 95th floor, it was nice to know a lounge like that was there: a clutch destination for entertaining out-of-town family and friends.

But this is Chicago, a city where food and drinking culture not only survives but often thrives — and in overlooked spots that may go unnoticed to the average passerby. To find a few great new destinations that are off-the-beaten path we called up Lauren Viera, the author of a compelling new pocket city guide called 500 Secrets, which catalogs hidden Chicago gems from bars to bookstores to places for a late-night bite.

Viera, who has covered the spirits and cocktail industry for local and national publications, including the New York Times, offered up six off-the-mainstream-radar spots to try in 2024.

* * *

Queen Mary

Courtesy of Queen Mary

Nick Murway

2125 W. Division St.

The theme is British maritime, and the vibe is a dark, romantic long bar that feels like you’ve stumbled upon a time capsule buffered from the world outside its doors. It’s so great,” Viera said. “It’s stuck in 1940. It was shuttered for almost 50 years. It’s a time capsule, and they restored it. It’s very understated and has a nice menu. Gin focused, but you can get anything there.”

* * *

The Office

955 W. Fulton Market

This speakeasy with vintage barware and specialty bottles sits below the well-known Aviary in the West Loop. “This is the place I always want to go on my birthday,” Viera said. “It’s an epic spot, and more pricey. The menu changes frequently, and you can trust whatever is on it will be vetted by some of the top mixologists in the city. They serve up a decadent hot fudge sundae that feels really, really fun and special.”

* * *


Kumiko interior

Jonas Jacob Svensson

630 W. Lake St.

This Japanese “dining bar” starts with drinks, then builds a food menu to complement it. It’s small and mostly requires reservations. “The owner was born and raised in Japan, and she incorporates her culture into the drinks,” said Viera. “You don’t have to drink alcohol, either; they have a really, really nice spirit-free menu, too. It’s a little tiny dining room off of Lake Street. But it’s special occasion, with a more formal arrival, and requires a reservation. People dress up, even though you can hear the El rumble overhead.”

* * *

The Milk Room

12 S. Michigan Ave. inside the Chicago Athletic Association

There are small bars; then there are microbars, like this low-lit one hidden in the Chicago Athletic Association hotel that has just eight seats. “I love that this bar is still going strong,” Viera said. “It’s a place where you show up, have a conversation with the bartender, and end up with the most special thing you’ve ever had. The cocktails rotate all the time, but you’re safe with anything. If you love a certain spirit – say Campari or rye or bourbon – this is the place to get the fanciest drink of your life and love it.”

* * *



Scott Baker Photo

11 E. Walton St., inside the Waldorf Astoria

The marble-and-leather accented bar reopened last fall after an extensive renovation. “It’s a hotel bar that isn’t like any other hotel bar,” Viera said. “It’s tiny, tucked away on the second-floor bar inside the Waldorf Astoria. I love it because the drinks are so delicious but it’s a place where bar snacks are equally on par.”

* * *

Easy Does It

Drinks and food at Easy Does It


2354 N. Milwaukee Ave.

A more casual entrant on the list. “Unlike some other spots on this list, this wine bar is a really casual find. It’s in Logan Square,” Viera said. “It’s not romantic or candlelit or sexy or anything, but it feels special because it’s tucked away and unpretentious and has a lot of interesting wines that appeal to a next generation of wine drinkers. There’s a handful of cocktails, too, if someone in your party doesn’t drink wine.”

Cassie Walker Burke is WBEZ’s external editor. Follow her @cassiechicago.

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