Bars and lounges for singles
Located in the Chicago Athletic Association, the sprawling bar has pool tables, a poker table, chess boards and a full bocce court, so there’s plenty of ways to strike up a conversation between rounds of affordable, well-made drinks from Paul McGee (Lost Lake).
The Bucktown favorite has a line on Friday and Saturday nights that’s worth the wait. Half bar and half apartment, the space will make you nostalgic for the house parties of your college days, if you aren’t still living them. Grab a glass of whiskey or dirt-cheap PBR and elbow your way into the crowd packed wall-to-wall with hipsters. Rotating DJs play everything from throwback 80s hip-hop to Brazilian samba, and there are plenty of dark candlelit corners to canoodle in if you hit it off with someone on the dance floor.
A haven for craft beer geeks, the Map Room is not your typical singles bar (in fact, we’d guess most spots on this list would be appalled by the moniker). While it’s worth the visit just for the constantly rotating selection of local and imported drafts and mile-long bottle list, the decidedly uneven ratio of men to women on any given night means ladies have their pick of the bearded-and-flannel-clad litter. Bonus: free pretzel sticks.
Andersonville’s neighborhood tavern is a cozy sports bar and a popular spot for the local lesbian community. The crowd is composed of well-acquainted regulars, and there’s an undeniably welcoming feeling of midwestern warmth and camaraderie among the group and bartenders. With a pool table, darts and jukebox to keep you amused and cheap drinks to keep you tipsy, it’s easy to sit back, relax and totally lose track of time.
The neighborhood bar attracts a crowd from far beyond Humboldt Park borders, thanks to a funky, taxidermy-filled interior; large backyard patio with a summer bar and string lights; and cheap beer and shots. The lowlife—a shot of whiskey or a pull from the amaro machine (like the old Jäger machines) plus a High Life—is just $5, and is more consistent than the ever-rotating list of cocktails.
Boystown mega-bar Sidetrack is a sprawling complex with at least six bars and tons of flat-screens playing old and new music videos. Despite all having the same drink selections (including a handful of frozen drinks that are dangerously powerful) each bar has a curiously different atmosphere. If you aren’t feeling the vibe in one, just head down the hall to check out the boy in the next room.
A bit of a wild card, the Peninsula is the perfect place to sip a martini with Chicago’s well-dressed and well-to-do set. The dark lounge interior filled with leather chairs and a cozy fireplace has all the charm of a library of a British country estate, complete with the eccentric personalities you might find in an Agatha Christie novel. Mingle with out of town guests, young professionals visiting clients on business or the bridal parties of trust-fund kids in town for a wedding.
Tucked inside the entertainment epicenter that is Thalia Hall, Tack Room is a hidden piano saloon that's decked out in equestrian-themed decor and wax-dripping candelabras. The menu here is a menagerie of expertly crafted cocktails, wine, bar snacks, entrees and desserts. Coordinate your visit with a rotating schedule of piano players, who take a seat every Thursday, Friday and Saturday at 9pm. Have your requests ready and your falsetto in tune.
Make yourself comfortable after work at Bub City, which has a decidedly more relaxed atmosphere than its surrounding River North counterparts. The easy-to-navigate drink list will keep beginners happy, while the seriously strong cocktails and bourbon collection will please even the pickiest drinkers. Syrupy-sweet country music and honky-tonk decorations give the space the feel of a Taylor Swift theme park. When dinner service is over the tables are cleared out so you’ll have plenty of room to two-step.
This popular, upscale Andersonville martini lounge serves up cocktails to a mixed straight and gay crowd, making it an equal opportunity meeting place.
One of the city’s classic people-watching spots in the Gold Coast, Tavern on Rush has an eclectic mix of young and old. Waitresses in tight, short matching dresses flit from table to table with trays of vodka and sodas and Scotch. The music here is muted, making it easy to hear above the restaurant clatter when chatting with the person next to you at the bar—a major perk if you find yourself flirting with someone out of your age range.
With a handful of intimate booths, a photo booth, pinball, late-night snacks and plenty of space to spread out, you’ll have no problem striking up a conversation at Pilsen mainstay Skylark. The well-curated draft list is ridiculously inexpensive (everything is $6 or under). Buy a couple rounds for the cutie at the other side of the bar (or tater tots for $4, which would work with us) and still have cash left for cab fare home.
The payoff from the nautical theme hinted at by this blue-collar hangout’s name is decidedly small. Aside from a light fixture made from a ship’s wheel and anchor-shaped coat hooks, this is your standard shot-and-a-beer dive. The crowd here is composed primarily of townies, with a bit of overflow from the U. of C. student-heavy crowd at nearby Jimmy’s.
We couldn’t pick just one of the dozens of places along the Wrigleyville strip, so we’re nominating them all. You don’t even need to be in one of the bars to be hit on—the sidewalk will usually do just fine. This area has got everything from dueling pianos and skeeball at Sluggers to a bar so minimalist it’s called Beer. When the Cubs are playing, the entire mess could be cordoned off as the basis of a Bachelor spin-off. Runners up: any late-night restaurants and convenience stores open past midnight in the vicinity.