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Nobody is going to look at you weirdly for wearing a blazer at most places though. Photo Credit: 180 N Morgan Taco joint by day, adult play place by night, Federales is a bonafide Chicago hookup staple. Hell, you could buy a very fashionable Armani long sleeved t-shirt and it could look better than a blazer does on people. Skylark 2149 S Halsted St, 312-948-5275 The three-to-one ratio of men to women at Skylark means ample pickings for the ladies, and its outwardly anemic vibe translates to little competition for any man trying out his moves.

 

Restaurants Restaurants are great places to pick up a more mature lady. Howl at the Moon is one of the best Chicago cougar bars This is one of the most famed Cougar bars in Chicago and makes no secret of being so. Chicago is full of energy and bursting with singles looking to meet up if you know the right spots.

 

Chicago's 8 Best Hookup Bars (And Your Crazy Hookup Stories) - The Readhead Piano Bar is one of the more upscale Chicago cougar bars that is fantastic if you are looking to meet a sophisticated older lady. We have put together a list of our favorite spots in the city where we have had the best success meeting single cougars not just in the Viagra Triangle.

 

During regular hours, this place is a highly entertaining cross-section of West Siders, but from 2 to 5am, it becomes a lawless, horny free-for-all, a kind of Wrigleyville West with more nonconsensual groping and fewer people who drove in from Schaumburg. Fauna Drunken girls in skinny jeans. Drunken men in funny hats claiming to work in the music industry. Our field notes from a recent trip include two one-sided games of grab-ass, four spilled drinks and six slurring suitors with European notions of personal space. John Barleycorn 3524 N Clark St, 773-549-6000 Every weekend, when the second floor of this distinguished-looking bar becomes Club Barleycorn, the regulars—affluent thirtysomething neighborhood professionals—are overrun by excitable suburbanites seeking mergers and acquisitions of the sexual kind. Fauna Observe Bob from accounting, wearing his going-out button-down and boot-cut jeans. Sexy ambience Big television screens, strobe lights, a smoke machine Mood music Britney, Maroon 5 Sleaze factor Moderate to high. Sexual displays are maximal, but on the plus side, traveling in large groups makes assault a remote possibility. Fauna We counted five ironic mustaches, four wool scarves worn indoors and seven pairs of large plastic glasses. Sexy ambience Sagging couches, a Viking figurine Mood music Art Brut, New Pornographers Sleaze factor Negligible. We witnessed only one woman in a corset throwing herself at the bartender while trying not to fall off her stool. Skylark 2149 S Halsted St, 312-948-5275 The three-to-one ratio of men to women at Skylark means ample pickings for the ladies, and its outwardly anemic vibe translates to little competition for any man trying out his moves. Fauna Mostly male, mostly bearded, and they seem to enjoy staring straight ahead. Its dark corners cry out for action, and its stable of top-notch DJs guarantees both a large weekend crowd and a little polite grinding. Fauna A rotating cast of spinners specializing in different kinds of music brings different faces on different nights, but patrons generally consist of the funky Bucktown condo owners and attractive twentysomethings who display their affinity for cultural institutions on tote bags. Sexy ambience Dim lighting, circular seating, DJ crates Mood music Bootlegs, B-sides Sleaze factor Low to moderate. While people make out on the dance floor, they do so with restraint.

The Lodge is a historic and popular venue, first opening its doors in 1957, and it maintains its distinctly retro feel. Restaurants Restaurants are great places to pick up a more prime lady. These are the trends we discovered. Ukrainian Village Somehow, Bar DeVille manages to be laid-back and quirky yet sexy, much like its patrons, who run the gamut from industry folks to creative types and hipsters. But a woman would rather hear that you're hookup bars chicago, if you get my responsible. Playing tennis, squash or any other team or social sport is a great way to meet an older lady. If you prefer a more manly venue to do your hunting, the Green Mill will be right up your street. Cougar Life which hookup bars chicago can is the note online dating site for helping guys find attractive older women to chat to, meet up with, and date. You can get ahead of the competition in this Chicago Cougar bar by dressing to impress. I doubt you will have any luck meeting women if you are by yourself at a bar. It all depends on where you are, your body type, and what looks good. Health and fitness is extremely important to these attractive older ladies and so if you head down to the gym you will almost certainly find them working out to keep themselves in top condition.