An Affair (Guide) To Remember

by Fred Schlatter - Citysearch Contributor - 311 Reviews - 33 Lists

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Updated: December 31, 2008

People cheat, regularly, but all that two-timing takes planning. Turns out Chicago is stocked with bars, restaurants, clubs and hotels known for safe access and unnecessarily strong drinks.

Where to Rendezvous

  1. 1 2 Star Rating: Below Average Second Story Bar
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    157 E Ohio St Ste 2, Chicago, IL 60611 (map)

    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.

  2. 2 5 Star Rating: Highly Recommended Hotel Cass Holiday Inn Express
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    640 N Wabash Ave, Chicago, IL 60611 (map)

    Despite a multi-million dollar renovation that took the long-time River North hotel from seedy budget hole 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.

  3. 3 3.5 Star Rating: Average Rainbo Club
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    1150 N Damen Ave, Chicago, IL 60622 (map)

    Hey, even hipsters stray. And what a place to be untrue. Cheap beer and hokey decor helps, but the open-minded crowd is what really makes this Ukrainian Village dive a standout swinger's destination. Actually, you get the distinct impression that there are a lot of couples here who come to, er, experiment. But, you know, they're down with that sort of self expression.

  4. 4 4 Star Rating: Recommended Cafe Absinthe
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    1954 W North Ave, Chicago, IL 60622 (map)

    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. 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.

  5. 5 Tokyo Hotel
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    19 E Ohio St, Chicago, IL 60611 (map)

    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.

  6. 6 5 Star Rating: Highly Recommended Zebra Lounge
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    1220 N State Pkwy, Chicago, IL 60610 (map)

    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. There's no way a witness's bleary-eyed testimony would stand up following a bender here.

  7. 7 4.5 Star Rating: Recommended Le Petit Paris
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    260 E Chestnut St, Chicago, IL 60611 (map)

    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? Nope, didn't think so. Exactly.

  8. 8 3.5 Star Rating: Average Blue Agave
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    1050 N State St, Chicago, IL 60610 (map)

    Here's the weird thing about this Gold Coast Mexican restaurant: It seems like it's made for an affair. And it is! Double-strength, gulp-able margaritas? Check. Secluded, second-story dining area? Check. Access off of the main strip? Check. Cheaters' gold!