An Affair (Guide) To Remember
By Fred Schlatter, Citysearch Contributor
Here's a sad reality: People cheat. Regularly. But all that two-timing takes planning, not the least of which is where to romance the targets of all those affairs. Turns out Chicago is stocked with bars, restaurants, clubs and hotels known for having conveniently unobtrusive environments, safe access and unnecessarily strong drinks.
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Le Petit Paris
260 E Chestnut St, Chicago, IL
Streeterville—which empties out after 6pm—is a terrific neighborhood in which to conduct an affair. There are very few street-level shops or restaurants and the foot traffic is limited to older locals hurrying home. This old-school French place is hidden in a residential building. It’s also dark—really dark. Here’s a test: Have you heard of it? Well, have you? Nope—didn’t think so. Exactly. -
The Zebra Lounge & Piano Bar
1220 N State Pkwy, Chicago, IL
Sure, two-timers run the risk of being spotted by people at McFadden’s and Bella while entering or exiting this tiny piano bar. But let’s be honest—those folks are pretty toasted at 1am on a Saturday. Actually, that’s probably the motivation for cheaters at this place—the drinks are strong and the crowd throws them back. There’s no way a witness’ bleary-eyed testimony would stand up following a bender here. -
Tokyo Hotel
19 E Ohio St, Chicago, IL
This most questionable of questionable hotels is a frank study in the economics of cheating. Rooms for the night are cheap. Rooms for an hour or two, cheaper still. There is no room service; there is no real service to speak of, other than a desk attendant who will take your cash—because of, you know, credit card records. -
Second Story Bar
157 E Ohio St Ste 2, Chicago, IL
Streeterville again, but this time the scene is a shady bar up a narrow staircase. This place is typically considered a gay hang—one of the few in the neighborhood—but a smattering of shifty-eyed singles and couples would suggest it’s also a popular rendezvous spot—gay or straight. -
Cafe Absinthe
1954 W North Ave, Chicago, IL
This might be for cheaters-light. It feels very illicit, what with the entrance in an alley and the absinthe reference and all, but it’s kind of tame really. That said, there are plenty of people on “dates” here. We bet there would be a few menu-shields going up if cameras started flashing. -
Rainbo Club
1150 N Damen Ave, Chicago, IL
Hey, even hipsters stray. And what a place to be untrue. Cheap beer and hokey décor helps, but the open-minded crowd is what really makes this Ukrainian Village a standout swinger’s destination. Actually, you get the distinct impression there are a lot of couples here who come to, er, experiment. But, you know, they’re down with that sort of self expression. -
Blue Agave
1050 N State St, Chicago, IL
Here’s the weird thing about this Gold Coast Mexican restaurant: It just seems like a seedy place for an affair. And it is! Double-strength, gulpable margaritas? Check. Secluded, second-story dining area? Check. Access not on a main strip? Check. Cheaters gold! -
Hotel Cass
640 N Wabash Ave, Chicago, IL
Despite a multi-million dollar renovation which took the long-time River North hotel from seedy budget hotel to respectable-looking-but-still-sort-of-budget, the Cass remains a notable stop on the cheater’s grand tour. The attraction here is plain and simple: It ain’t the Ritz, but it sure ain’t one of those motels near Midway either.
