You can’t talk food and drink in Chicago without a nod to The Bear. The FX show about the life of a restaurant and its dysfunctional family—with heart!—has included a number of cameos by Windy City restaurants and the people behind them. Chicago has always had a strong restaurant and bar scene, but now it seems everyone wants a slice at Pizza Lobo or a reservation at Ever, the fine-dining institution featured in the brilliant “Forks” episode in season 2 and the finale of season 3. The series has been a boon to gastro-tourism in the city.
Even the namesake restaurant of The Bear is symbolic of what makes Chicago such a perfect place for hitting the town. A line forms for humble Chicago beef sandwiches by day, and an ever-changing menu—it’s a nonnegotiable!—that aims for the sublime is served at night. Every city has its mix of high and low, but Chicago’s blend feels genuine, heartfelt, honest. Over the past few years, you’ve often been able to find elements of both in one place. At Sportsman’s Club, one of the de facto living rooms for folks who work in the hospitality industry, you can get a deftly made daiquiri in a place with the vibe of a tried-and-true tavern. At John’s Food and Wine, during happy hour you can indulge in a “Chicago Happy Meal”—a freezer-cold dirty martini and decadent beef-fat fries with melted leek aioli. Kasama, among the best Filipino restaurants in the country, serves croissants by day, and at night it’s a tasting-menu spot.
Casualness and elegance with a welcoming midwestern easiness are what make Chicago an ideal city for devoting an evening (or two or three) to the fine art of bar and restaurant hopping. These are the best places to enjoy a big night out.
Sportsman’s Club
THE PLACE TO FIND EVERYONE
Sportsman’s Club
With picnic tables out back where you can have an Old Style on a hot day and taxidermy animals on the walls inside (a nice accompaniment to any whiskey drink), Sportsman’s feels like a textbook neighborhood tavern. But thanks to some expert bartending, it’s a top-notch place to get a pretense-free co*cktail to begin or end your evening.
THE NEW co*ckTAIL TEMPLE
Meadowlark
It’s a speakeasy with a neighborhood-bar vibe, but you’re here for the drinks dreamed up by beverage director Abe Vucekovich, which include mesmerizing co*cktails themed around a single concept, like birds of the Midwest or the 1893 Chicago World’s Fair.
THE OLD-SCHOOL STOP
Green Mill co*cktail Lounge
The history is palpable at the Green Mill, one of America’s longest-running jazz venues and an old Al Capone hangout. It feels like nothing has changed since the ’40s, and we hope it stays that way.
The kitchen fire at Warlord.
LATE-NIGHT EATS
Warlord
It’s dark, it’s loud—expect metal, punk, or hip-hop to be blaring—and it’s among the most fearless restaurants in Chicago today. Here it’s all about daring food cooked over the fire, like the foie gras basted in butter and sugar. It just works.
THE QUINTESSENTIAL MARTINI
Cherry Circle Room
Located in the landmark Chicago Athletic Association hotel, the CCR evokes a secret members club, but it is, in fact, for everyone. Marvel at the cherrywood millwork and grab a martini to complete the mid-century time warp.
THE PRE-WRIGLEY BEER SPOT
Nisei Lounge
Wrigleyville is a drinker’s paradise, teeming with drunks who spill out of overly lit sports bars. A five-minute walk from the ballpark is this proper dive bar that offers cold Old Style and respite from the crowds. Grab a quick one before the game or post up all afternoon. There are still drunks, but at least they’re locals.
This article appeared in the Sept 2024 issue of Esquire
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REBIRTH OF AN OG
Ramova Theatre
Built in 1929 as a movie palace, Ramova shuttered in 1985 but survived demolition and made the National Register of Historic Places. It’s now reopened (with investors including Chance the Rapper) as a music venue, bar, and grill. Go for a show or an IPA and a bowl of chili—or all of the above.
The grill at Asador Bastian.
A RESERVATION TO SCORE
Asador Bastian
While most Chicago steakhouses are big, boisterous joints, Bastian is like a dinner party in a townhouse. Modeled on the asadores of Spain, it specializes in one boutique type of beef, called a txuleton in Basque. Don’t skip the arroz cremoso.
The 3 Best Bar-Seat Meals
Maxwell’s Trading.
Maxwells Trading
Chef and partner Erling Wu-Bower has parents who are Chinese and Creole. Executive chef Chris Jung is Korean. Both grew up in diverse cities, and Maxwells Trading features an eclectic menu that reflects that, executed with great refinement. Don’t miss the French onion dip with griddle bread, a cross between naan and a scallion pancake.
John’s Food and Wine.
John’s Food and Wine
The name is simple. The food and wine are not. Little revelations happen here, whether it’s an inexpensive grower Champagne you’ll want by the case or the best potato salad you might ever have. (It comes with the octopus.)
Chef’s Special co*cktail Bar.
Chef’s Special co*cktail Bar
It’s all about Chinese American classics with cheffy finesse here. Think egg rolls with a shu-mai-like filling or a bone- in pork shank with black-bean sauce. And the drinks, like the lemongrass gimlet, do not disappoint.
