Cindy’s

If you’re still remembering the summertime queues snaking past the elevator here, cheer up: Cold weather means no waiting for a perch at this rooftop spot. Like Milk Room (No. 3), it’s part of the Chicago Athletic Association Hotel. Reminiscent of a Great Lakes vacation house, complete with wood and picnic tables, Cindy’s delivers insane … Read more

GreenRiver

GreenRiver’s perch on the 18th floor of a medical building may put you off. But with one of Julia Momose’s intricate yet effortless cocktails in hand, you’ll forget all about the odd location. Leaning on the bar alongside a tie-loosened after-work crowd, you’ll realize that high-end cocktailing doesn’t have to be fussy to draw a … Read more

Band of Bohemia

It’s a beer hall for people who wouldn’t otherwise be caught dead in one. This well-appointed space blurs the line between bar and restaurant, offering seasonal small plates matched to five carefully considered brews. Thanks to the deft touch of brewmaster Michael Carroll (who in a past life was Alinea’s baker), these beers drink like … Read more

Lost Lake

The city’s best new bar is . . . a tiki bar? Didn’t Chicago name a tiki bar the best new drinking spot in 2014, too? Why is this magazine so obsessed with tiki bars? Yes, yes, and truly, we’re not. But when the legendary bartender Paul McGee (Whistler, Three Dots and a Dash) concocts … Read more

Pub Royale

A British-Indian bar on increasingly bland Division Street could have been a mess of subcontinental kitsch and curry. Instead, in the able hands of Heisler Hospitality (Sportsman’s Club), it’s more Darjeeling Limited than colonialist throwback. Despite “pub” in the name, the focus is on refreshing cocktails, with a whole section devoted to Royale Cups (fruity … Read more

Best Intentions

Logan Square may have lost the beloved neighborhood bar Marble, but a cozy corner tavern stepped into its place, perfect if you love the Pixies and dream of drinking angostura bitters on draft (shots are available for $4 a pop). A cushioned bar ledge cradles your elbows while you down sorta fancy cocktails, chat with … Read more

Broken Shaker

The boundary-pushing award goes to this Miami import, where bartenders use everything from pork bitters to porcini mushrooms in the 15 original cocktails. Though the Chicago-inspired concoctions sometimes miss the mark, the daily punch—on one recent visit, a combo of blood orange and rum—always scores. The bar is inventive enough to entertain both trend-chasing River … Read more

Breakroom Brewery

It ain’t the out-there Band of Bohemia (No. 4), but Breakroom exceeds expectations with its broad beer menu, impressive hand-carved bar from the woodworking shop next door, and more than enough room for you. And your date. And your 12 closest friends. 2925 W. Montrose Ave., 773-564-9534 Crowd Neighborhood couples on laid-back date nights Food … Read more