Is the best bar in Chicago really a gin joint in once-downtrodden Logan Square that has barely celebrated its first birthday? Hell yeah. For one thing, this place has serious craft cocktail cred: Co-owner Danny Shapiro apprenticed with mixology whiz Paul McGee at The Whistler (No. 5). Now he’s turned a barely marked corner spot on West Armitage Avenue into a refuge for both the blossoming creative class who live nearby and innovative-cocktail lovers who aren’t skittish about drinking outside the box (and won’t say no to a free cookie at midnight). Flush with lovingly salvaged furnishings, locally produced spirits, and a devoted staff who elevate the once-sidelined juniper berry-based spirit, Scofflaw easily tops all the taverns in the city.
Who’s there: Cocktail connoisseurs, mellow 30-somethings, every other bar’s bartenders
What to order: Swizzle #3 (Death’s Door gin, rum, Lillet blonde, passion fruit, lime, orgeat, bitters)
Find it: 3201 W. Armitage Ave., 773-252-9700, scofflawchicago.com
2. Big Star
Maybe it’s the whiskey shots talking, but there’s nothing better than a Saturday night spent gorging on pork belly tacos, guac, and margaritas—especially when the team behind standout restaurants Avec and Publican makes them. In good weather, this Wicker Park hot spot’s backyard party vibe seals the deal: If you land a stool, park there for the night. You won’t regret it (until the next morning).
Who’s there: Relaxed day-drinkers followed by a boisterous nocturnal crowd
What to order: The Big Star Margarita or $3 whiskey shot du jour
Find it: 1531 N. Damen Ave., 773-235- 4039, bigstarchicago.com
Photograph: Courtesy of Bar
3. The Aviary
Like tattooed, mustachioed mad scientists quarantined in their lab, mixologists gather behind an illuminated wall, where they are obscured by billows of dry ice and steam. (The Aviary’s owner is Grant Achatz, chef of boundary-pushing restaurant Next, which adjoins it). The experience—while hard on your wallet—is not to be missed.
Who’s there: Fiscally blessed foodies craving a show
What to order: In the Rocks (rye, bitters, and vermouth cocooned in a hollow ice cube)
Find it: 955 W. Fulton Market, 312-226-0868, theaviary.com
4. Maria’s Packaged Goods and Community Bar
Named for the owners’ mother, Maria Marszewski, who bought it in 1986, this Bridgeport anchor got spruced up two years ago with art deco accents and reclaimed materials. But it’s still an enormously appealing come-as-you-are store-slash-tavern—the best place to drink good beer on the South Side.
Who’s there: Craft brew enthusiasts from all over the city
What to order: Beer (obviously). There are 450 varieties on offer.
Find it: 960 W. 31st St., 773-890-0588, community-bar.com
Photograph: Marian Frost
5. The Whistler
Inventive cocktails at reasonable prices. DJs, live music that spans genres, or Movieoke (exactly what it sounds like) every night, sans cover charge. What’s not to like?
Who’s there: Artsy locals and the occasional barhopping bro
What to order: The Quill (a pseudo negroni with absinthe)
Find it: 2421 N. Milwaukee ave., 773-227-3530, whistlerchicago.com
Photograph: Robert Brenner
With 20 or so offerings by the glass (most under $10) and a low-key vibe, this wine bar eschews the standard stuffiness. The owners stock their pond with mostly Old Worlds but liven up the mix with nontraditionals from small family producers and biodynamic operations. Reading the list can enlighten even seasoned oenophiles.
Who’s there: Canoodling couples and neighborly wine drinkers of all stripes
What to order: 2010 Tire Pé Diem Bordeaux
Find it: 954 N. California Ave., 773-292-1616, rootstockbar.com
Photograph: Katie Stratton
This moody lounge in the Raffaello Hotel, with its couch-filled nooks and intimate terrace, scores high in ambiance. And it pours a stellar cocktail, thanks to the addition of Craig Schoettler (formerly of the Aviary, No. 3) behind the bar.
Who’s there: Corporate card carriers, Gold Coast glitterati
What to order: The Pineapple (green Chartreuse, pineapple juice, lime juice, mint)
Find it: 201 E. Delaware Pl., 312-943-5000, drumbar.com
8. Half Acre Tap Room
This 70-seater adjacent to the lauded Northcenter brewery has a singular focus: Half Acre beers. There are no TVs, no swizzle sticks, and no nibbles—but the owner doesn’t mind if you bring in food.
Who’s there: The brew equivalent of locavores
What to order: Sticky Fat (a dark ale)
Find it: 4257 N. Lincoln Ave., 773-248-4038, halfacrebeer.com
Tattooed metalheads rub shoulders with spirits snobs at this underlit late-night purveyor of head-banging music, cutthroat pool playing, and more than 500 (gulp!) whiskeys.
Who’s there: Preppy locals, people with piercings
What to order: Parker’s Heritage Collection ten-year-old wheated bourbon
Find it: 2771 N. Lincoln Ave., 773-472-2771, delilahschicago.com
Photograph: Courtesy of bar
10. Joie de Vine
What started as a local wine bar with a lesbian fan base has evolved into a destination for craft beer hounds who prefer their suds without the scene. The beer tally now tops 90, and a custom cocktail program will wow your friends who appreciate small-batch distilleries and regional producers.
Who’s there: Scene-averse tipplers
What to order: Name the liquor you like and let them figure it out
Find it: 1744 W. Balmoral Ave., 773-989-6846
Photograph: Courtesy of bar