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How to Spend a Night in Chicago

For night owls, travel junkies, and adventurers alike.

Chicago is famous for gangsters, having a bunch of red meat, and wind, but there is actually more to it than that! It’s got a fantastic nightlife scene, especially if you know where to look, and nobody in Chicago minds leaving their lights on a little later for the right crowd. If there’s one key to enjoying this town and its locals, do as Chicagoans do: Be direct, but don’t be a jagoff. Come hungry and thirsty, and know which tourist traps to avoid and and where wanderers will always be embraced—an easy task with this handy dandy guide to a Chicago night.

7–8 PM

SMOKED TROUT ON THE CALUMET RIVER

Just west of the Indiana border sits a little white smoke shack called Calumet Fisheries. Look in one direction and you’ll see a vista of Midwestern dreariness. Look in another and you’ll see the city’s glistening skyline. Look in any direction, and you’ll smell smoked fish. The rainbow trout is a must, and it’s worth a few extra bucks to add a pound of smoked shrimp to any order. It’s also important to come with a firm understanding of the "Chicago lean." That’s eating while standing, elbows on the counter, food no more than 12 inches from your mouth.

8–9 PM

STRANGE GAMES IN THE WEST LOOP

The best way to blow off steam is by throwing axes at stuff, so be sure to stop by Bad Axe Throwing in the West Loop for an early-evening stress reducer. This big, bright warehouse could very well be the laboratory that spawned the Chicago hipster male (flannel, bushy beard, knit hat), but it’s all about substance over style when it comes to hucking axes. After a little starter education, the coaches at Bad Axe cut their students loose for a series of tossing competitions. Within an hour even a beginner axe-slinger can expect to achieve lumberjack status.

More to do nearby:
For bocce ball, it’s all about the backyard scene at Saint Lou’s Assembly, followed by a quick stumble next door into sister bar Moneygun, which expertly crafts classic cocktails. Or, try some karaoke and Szechuan bar snacks at 2Fun Chinese.

9–11 PM

BRISKET, PICKLES, AND DRINKS ON THE WEST SIDE

Avoid the scenesters on restaurant row by dipping downstairs to Green Street Smoked Meats. Order a pitcher of Chartreuse Mules and two sides of spicy pickles for the table. The chopped brisket is the move for the main, unless you really give zero fucks, in which case just go for the Frito pie.

More to do nearby:
Fox Bar (at Soho House) is open to the public and has a pay phone that magically only dials out to pizza. Lone Wolf does a great job warding off all of the basics and bros that spill out of the nearby Parlor Pizza Bar.

11 PM–3 AM

BAR CRAWL IN UKRAINIAN VILLAGE

Head to Ukrainian Village and the surrounding neighborhoods for the classic Ukrainian and Polish Chicago bars that line the streets of the west side. Start off at Zakopane on Division Street, where the jukebox is so bad it’s good (we recommend the obscure Polish cover of Elvis Presley’s "Are You Lonesome Tonight"). Choose from an array of tallboys and chase everything down with a shot of Malört. Disclaimer: You will be judged fiercely if you make a face while drinking Malört.

More nearby: Ola’s Liquors, Phyllis’ Musical Inn, and Stella’s Sports Bar make for a good lap. Then wash all that shitty beer down with a proper cocktail at Sportsman’s Club on Western Avenue.

3–5 AM

DANCING UNTIL DAWN OFF OF THE RED LINE

Hit up the after-hours jazz party with Sabertooth at the Green Mill. This Uptown soul, jazz, and swing club still feels like the 40s without pushing a falsely vintage agenda. Everyone at the Mill has a story about the joint. Capone? Check. Stabbings? Check. Sinatra, Holiday, Gillespie? Yep, all the greats. Underground tunnels during Prohibition? You know it.

More nearby: Soak up the glory of Boystown at Roscoe’s Tavern or the legendary punk scene at Exit Chicago in River West. Either way, expect light to heavy bondage.

5–6 AM

SOMETHING SPICY AT UNCLE MIKE’S

Deep dish is for tourists. When it’s time to soak up and sober up it’s all about the traditional Filipino breakfast at Uncle Mike’s Place. (Of course, this is more like third dinner for you, but don’t overthink it.) Tocino, longaniza, and hot and spicy spam for the table, please. Often Mikey himself waits tables, so don’t turn down that free bowl of lugaw—a chicken lemon rice soup kicked up with green onions, fried garlic chips, and plenty of ginger.

6–7 AM

SUNRISE ON LAKE MICHIGAN

Head to Promontory Point to watch the sun come up from a rocky little beach. (Note that the perspective from the Southside affords a view of the epic Chicago skyline on its good side.) Impress friends by pointing out the 311 South Wacker Building to the left, a postmodern masterpiece. Take a dip if you dare, but expect a low rating from your Lyft driver if you leave a drenched backseat in your wake.

All photos by Isis Jenkins.