Ultimate Singles Guide

1383 N Milwaukee Ave, Chicago, IL 60622 (map)

Cabaret crooning strikes a sultry tone at this swanky, velvet-bedecked piano bar--a haven for the more mature set in young, trendy Wicker Park--where bubbly lovers and single malt sippers unite.

444 N la Salle Dr, Chicago, IL 60654 (map)

Mature in feel, this tri-level River North pub is a civilized place to make eyes if you're so inclined. But it's also a spot to kick back, Pimm's Cup in hand, over British eats like Newcastle-battered fish and chips.

5464 N River Rd, Rosemont, IL 60018 (map)

Big, bigger and biggest is the mantra at this carnivore's den that's legendary for steaks and football-sized lobster tails. But if it's a connection you seek, sidle up to the bar, eye the suit across the room and hope he sends a massive martini your way.

151 W Erie St, Chicago, IL 60610 (map)

Well-dressed professionals swill the namesake drink at this luxe playground. Despite the crowds, there's plenty of room to roam: Tables, a stage showcasing nightly acts and a sprawling patio help control the flow.

1031 North Rush St, Chicago, IL 60611 (map)

Dig into steak, and lots of it, at this venerable Gold Coast meat market where digit swapping and people watching are standard pastimes. Just watch out for tourists and cougars. Unless, you know, that's your thing.

16 W Ontario St, Chicago, IL 60610 (map)

Flirt the night away at this spirited piano bar, where vets join in song and onlookers peruse the dimly lit, perpetually packed room. A lengthy list of single malts, tequilas and bourbons helps lube conversation.

12 W Elm St, Chicago, IL 60610 (map)

Carefully groomed and outfitted tipplers, plenty of them ironically clutching brown-bagged 40s, pack this petite, industrial-chic watering hole. Of course, deejays offer a diversion (and motivation to booty shake) if that's your thing.

600 W Chicago Ave, Chicago, IL 60610 (map)

Dress to impress when bound for this swanky, moodily lit sushi house. The chic, lower-level lounge, rendered cooler by low-slung furniture and gracious river views, boasts fabric-draped cabanas that invite scoping.

22 W Hubbard, Chicago, IL 60610 (map)

A sib to The Underground, this unpretentious, space designed by Nate Berkus, heats up during the wee hours. Come early to tackle a Kobe burger downstairs; then ascend to the sceney second-floor lounge, where matches are most likely to be made.

226 W Ontario St - Entrance in Alley, Chicago, IL 60610 (map)

Slinky clothing--short skirts on girls, tight tops on guys--is de rigueur at this hedonistic hang with countless bars, multiple deejay booths and plenty of space to shimmy.

56 W Illinois St, Chicago, IL 60610 (map)

Capture the date of your dreams (or at least spot celebs) at this bomb shelter-themed hot spot in River North. Just order a few cocktails, many with military-chic names, before putting your strategic ops into action.