There are so many places to chase tail in the windy city, and we’ve tracked down the 5 best cougar bars in Chicago. Sure, you could browse web profiles on cougar sites online, but for those that enjoy the thrill of the chase, brush up on your martini lingo and hit the trail at these hunting grounds.
- The Lodge. It may not be the nightclub strip in Vegas, but the Rush & Division St. bar strip in Chicago is known for two things: tourists and late-night bars. Opened in 1957, the Lodge has maintained the retro décor and the older clientele. When the business meetings end, the bar turns into an adult playground. Shimmy up to the jukebox, play a little “Mrs. Robinson”, and let the cards fall as they may. The drinks here are cheap enough to afford yourself, but you won’t be buying for long. 21 West Division Street, 60610. (312) 642-4406 Best Night to Go: Saturday night, bars are open an extra hour.
- Howl at the Moon. We’re reluctant putting this in our top five, but you just can’t ignore that this bar has a cougar theme night every Thursday. The $5 cosmos and huge dance floor bring out the babes, but any bar that promotes cougars can turn into a sausage-fest of guys with the same filthy mindset as you. If you’re up for the challenge, bring a fat wallet and your best dance moves to Howl at the Moon. 26 West Hubbard St., 60654. (312) 863-7427 Best Night to Go: Thursday. Duh.
- Martini Park. Nothing attracts a cougar like a berry martini and danceable music. No bar does that better than Martini Park. Try not to be overwhelmed by the ratio of available tail to cougar hunters. You’ll have to leave your balls at home to sip flavored vodka out of a stemmed glass, but don't worry, so will every other guy there. If you know how to sing or dance, break the ice on a night that features live-band karaoke or swing music. 151 W. Erie Street, 60610. (312) 640-0577 Best Night to Go: Wednesday for live-band karaoke.
- The Redhead Piano Bar. All 4 a.m. bars are known for guys circling like sharks, ready to close the deal. The best way to improve your odds? Make sure you’re the only young piece of ass in the bar. We did our homework, and found a joint that doesn’t let douche bags past the front door. Redhead’s dress code stipulates no hats, sneakers, torn jeans, sweats or t-shirts. Now that we eliminated half your wardrobe, don your sexiest work attire and slip downstairs to the Redhead. With martinis named “the James Bond” and the “Madame Rouge,” this live-music bar keeps the cougars coming (and with some luck, your only competition will be balding, beer-bellied guys twice your age). 16 W. Ontario Street, 60654. (312) 640-1000 Best Night to Go: Thursday, we all know that’s when the weekend really starts.
- The Green Mill. This is our hands-down favorite. Not only is it a cougar bar, this speakeasy is a real man's kind of joint. The Green Mill’s history is rich with ties to the mob, bootlegged liquor, and some of the most notable stars and gunslingers to hit the streets of Chicago. Today, this music venue still rocks a 1940’s aesthetic, hosting jazz and swing acts from all over the country. If you catch some hot cougar tail here, it’s just as bonus on top of what is sure to be a great guys’ night out. 4802 N. Broadway Avenue, 60640. (773) 878-5552 Best Night to Go: Check out the music calendar for the best nights to go.