When talking about food and drink in Chicago, you can’t help but The bear. The FX show about the life of a restauranteur and his dysfunctional family—with heart!—featured several guest appearances from the Windy City’s restaurants and the people behind them. Chicago has always had a strong restaurant and bar scene, but now everyone seems to want a slice at Pizza Lobo or a table at Ever, the foodie institution featured in the brilliant “Forks” episode in Season 2 and the Season 3 finale. The series has been a boon for food tourism in the city.
The restaurant of the same name by The bear is a symbol of what makes Chicago such a perfect place to stroll around town. During the day, a line forms for simple Chicago beef sandwiches, and at night, they serve an ever-changing menu—that’s non-negotiable!—that aims for the sublime. Every city has its mix of high and low, but Chicago’s mix feels genuine, warm and honest. In recent years, you could often find elements of both in one place. At Sportsman’s Club, one of the de facto living rooms for people who work in the restaurant industry, you can get an expertly mixed daiquiri in a place with the atmosphere of a tried-and-true tavern. At John’s Food and Wine, you can enjoy a “Chicago Happy Meal” during happy hour—an ice-cold dirty martini and decadent beef-tart fries with melted leek aioli. Kasama, one of the country’s best Filipino restaurants, serves croissants during the day and offers tasting menus at night.
Casualness and sophistication with the welcoming ease of the Midwest make Chicago an ideal city to dedicate an evening (or two or three) to the art of bar and restaurant hopping. These are the best places to enjoy a great night.
Sports club
The place where you can find everyone
With picnic tables in the backyard where you can sip an Old Style on a hot day and stuffed animals on the walls inside (a nice accompaniment to any whiskey drink), Sportsman’s feels like a typical neighborhood bar. But thanks to the expert bartenders, it’s a prime spot to start or end your evening with a no-fuss cocktail.
The bar at Meadowlark.
THE NEW COCKTAIL TEMPLE
It’s a speakeasy with a neighborhood bar vibe, but you’re here for the drinks dreamed up by beverage director Abe Vucekovich, which includes intriguing cocktails centered around a single theme, like Midwestern birds or the 1893 Chicago World’s Fair.
The old-school stop
At Green Mill, one of America’s oldest jazz venues and a former hangout of Al Capone, history is palpable. It feels like nothing has changed since the ’40s, and we hope it stays that way.
The kitchen fire at Warlord.
LATE NIGHT DINING
It’s dark, it’s loud – expect blaring metal, punk or hip-hop music – and it’s one of the most fearless restaurants in Chicago today. It’s all about daring dishes cooked over a fire, like the butter-and-sugar-spiced foie gras. It just works.
THE QUINTESSENTIAL MARTINI
Located in the famous Chicago Athletic Association hotel, CCR is reminiscent of a secret members’ club, but is actually open to anyone. Admire the cherry wood carpentry and grab a martini to complete the mid-century feel.
The beer spot in front of Wrigley
Wrigleyville is a drinker’s paradise, full of drunks pouring out of overlit sports bars. A five-minute walk from the stadium is this proper dive bar that offers cold old style and a break from the crowds. Grab a quick beer before the game or stay all afternoon. There are still drunks, but at least they’re locals.
This article appeared in the September 2024 issue of Esquire
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REBIRTH OF AN OG
Built in 1929 as a movie theater, the Ramova closed in 1985 but survived demolition and was listed on the National Register of Historic Places. It’s now reopened (with investors like Chance the Rapper) as a music venue, bar and grill. Catch a show or an IPA and a bowl of chili — or all of the above.
The grill at Asador Bastian.
A reservation to score points
While most steakhouses in Chicago are big, loud places, Bastian is like a dinner party in a townhouse. Modeled after the asadores of Spain, it specializes in a boutique style of beef known as Subscribe in Basque. Don’t miss the Arroz Cremoso.
The 3 best meals at the bar table
Maxwell’s trade.
Chef and partner Erling Wu-Bower’s parents are Chinese and Creole. Chef Chris Jung is Korean. They both grew up in different cities and Maxwells Trading offers an eclectic menu that reflects this and is prepared with great sophistication. Don’t miss the French onion dip with fry bread, a cross between naan and a spring onion pancake.
John’s food and wine.
The name is simple. The food and wine are not. There are little revelations here, whether it’s a cheap champagne from the producer country that you want by the case or the best potato salad you’ve ever had. (It’s served with the octopus.)
Chef’s special cocktail bar.
It’s all about Chinese-American classics with chef’s finesse. Think spring rolls with a shu mai-like filling or a bone-in pork knuckle with black bean sauce. And the drinks, like the lemongrass gimlet, don’t disappoint.
