Guys Night Out

632 N Dearborn St, Chicago, IL 60610 (map)

Low-key bars can be nice, but sometimes you just want to go to a crowded club, get out in the middle of the floor, and dance the night away with a bunch of gorgeous 20-somethings. Vision boasts some of the hottest tunes mixed up by some of the best area DJs. So if a laidback guys? night sounds boring to you, just ditch that quiet barstool and check out one of the most happening parties in Chicago.

108 E Superior, Chicago, IL 60611 (map)

Your father?s a better drinker than you are, and your father?s father was even better. It?s just a fact of life. Now you can give up and chug a few beers or you can take dad?s example and add some class to your drinking regimen. Put on some nice clothes and keep it simple: Resist the urge to order a ?brewski? and, with an air of self-assurance, look the bartender straight in the eye and ask for a martini. You may never best the old man, but at least you can inspire your own sons.

3741 N Southport Ave, Chicago, IL 60613 (map)

The Irish are some of the most fun-loving and hospitable people in the world, so of course an Irish pub is going to serve up just as many warm welcomes as pints of Guinness. Grab a stool in front of the massive wooden bar or fill up a booth with your buddies. Just take it easy. Strike up a conversation with the mostly Irish bar staff or enjoy the live music.

1059 W Addison St, Chicago, IL 60613 (map)

If sports are more of your game, where better to go then this Wrigleyville bar right across the street from Wrigley Field itself. Over 100 screens throughout the bar ensure that you won?t miss a moment of the action. A variety of good daily specials like two dollar domestics mean that you and the boys can get loaded without emptying your wallets.

464 N Halsted St, Chicago, IL 60642 (map)

Cigars manage to convey class while still maintaining an image of manliness, so ditch the cigarettes and join the big boys. This unique cigar shop carries 9 of its own different blends, and the owner is happy to help you find a handrolled cigar to match your tastes. And remember to pick up some matches so you don't ruin the flavor with a lighter.

777 Casino Center Dr, Hammond, IN 46320 (map)

Sure, Chicago doesn?t allow gambling within the city limits, but just across the state line it?s all flashing lights and clanging bells, laying 20 bucks on red, and doubling down. Some might say gambling?s irresponsible, but they?re the same people who say two drinks in a sitting is binge drinking. So ante up and live big like Jim Sturgess in ?21.?

10 S LaSalle St Ste 210, Chicago, IL 60603 (map)

If you really want to make heads turn, that suit from the clearance rack just isn?t going to cut it. Besides, it?s not going to fit you very well anyway. With a 45-minute style consultation and 23 measurements, owner Sonny Balani makes sure that you get the best look possible for your money. Custom suits might take a little longer, but it?s worth it when you get to choose every detail right down to the fabric itself.

1400 E Touhy Ave, Des Plaines, IL 60018 (map)

When you finally go out with the guys, you?ve got a few options for getting there. You can drive yourself and worry about parking--not to mention getting home afterwards. You can suffer the indignation of taking public transit. Or you and your crew can turn heads as you step out of your limo and waltz right past the plebian masses waiting to get into the bars.