Downtown bar in Chicago's River North
Downtown: Everything’s waiting for you

For the first hour of a recent Saturday night at Downtown—a new bar in the space once occupied by Gentry and, ever so briefly, The Lucky Lady—I was the only lady in the room. Among the lounges that dot River North, Downtown stands as the sole gay bar save for the stalwart dive Second Story in nearby Streeterville. As a veteran of many a Boystown bar hop, I had decided to visit both spots and evaluate the possibility of a new gay district on Chicago’s nightlife horizon.

With three male companions in tow, I headed to Downtown first, since I’d heard happy hour is bus-t­ling (my next visit will be for Talentless Tuesdays karaoke in the basement). Relieved to find the drink list unencumbered by craft cocktails or hundreds of beers to sift through, I ordered my old faithful, Maker’s and Diet ($8), and huddled with my group under the dramatic barrel ceiling. “Oh, yeah. There’s a lot of Grindr action going on here,” my friend Tim muttered, peeking at the so-named smartphone app that lets like-minded seekers of, ahem, certain favors zero in on one another, wherever they may be. You wouldn’t have known such a thing was going on from the looks of the crowd, an all-ages mix of fetching, well-dressed men who seemed to be engaged in conversation with friends—or at least not blatantly checking their iPhones.

Next we watched a husband and wife, no doubt guests at a nearby hotel, walk in and stand for a long, confused moment before taking two seats at the end of the bar. “Is this a common occurrence?” I later wondered aloud to Downtown’s owner, Brian Martin, who most recently managed the restaurant Eve. “You get the occasional tourist who takes a look around and announces he wouldn’t be caught dead having a drink here, but mostly they just ask if it’s a gay bar and then they stick around,” he replied. Once the crowd diversified and a few more women arrived, I found myself thinking I might not know this was a gay bar if I wandered in on a lark. The space looks like a spiffed-up version of any neighborhood pub: pretty light fixtures, fresh paint, lots of flat-screens tuned to sports.

After cocktail number two, we bundled up and walked the few blocks to what I fuzzily remembered from a prior visit as Second Story’s address. After blithely marching past an open door, I wheeled around: “That’s it! Those red-carpeted stairs!” (People who have worked on the block for years might not realize Second Story exists, but most gay men do. It’s legendary, if slightly downtrodden.)

“Hiiii, purdy lady,” slurred one of the less coherent patrons, reeling past as we walked in. A compliment! I knew this was my kind of place. We found seats and ticked off the elements that give Second Story its particular je ne sais quoi: the bar itself, which meanders, mazelike, along the east wall; the murky eau-de-dishrag aroma; the monitors that broadcast patrons’ comings and goings on those red stairs; and the crowd of genial middle-aged men. Thinking of no other way to break into a conversation, I tapped one of these gents on the shoulder and began grilling him about his nightlife habits. Do you come here often? “Yes, we live down the street,” said Paul, nodding to his partner. Where else do you go? “Mostly hotel bars, like The Wit or The Peninsula.” Have you been to Down­town, and if so, what did you think? “We saw men there who we’ve never seen out, which is good.” Do you ever hop from Second Story to Down­town? “Sure,” Paul said. “It’s a relief not to have to take a cab all the way up to Boystown.”

Thirsty, I remembered some­­thing else from my last visit. “It’s cash only,” I whispered to my date. Between the two of us, we scrounged up $8, just enough for two Buds, plus tip. Watch out, Boystown—and you, too, River North cocktail lounges. Chicago’s budding Mag Mile gay district is straight- and budget-friendly.

GO: Downtown 440 N. State St.;; Second Story 157 E. Ohio St., second floor; 312-923-9536


Photograph: Chris Guillen