3452 N. Halsted St., 773-975-9244
Best new Boystown bar: Any neighborhood would be lucky to get a bar like Elixir as its new watering hole. But, considering that this upscale cocktail lounge somehow landed on a rowdy strip of beer-and-shot bars, Boystown needed it most of all. Natives can escape into this serene, intimate space where down-to-earth bartenders take time to transform top-shelf booze into pitch-perfect Negronis, old fashioneds, and other classics. There’s often a wait. It’s justified.
2624 N. Lincoln Ave., 773-857-0421
Best new cocktail bar: This Lincoln Park newcomer with a menu of more than five dozen cocktails entered a crowded field. Alongside rotating modern concoctions, the offerings include classics we’d never heard of (Bizzy Izzy, Bliz’s Royal Rickey) and several we wish we’d started drinking years ago (the Mamie Taylor pairs Scotch with ginger beer and lime juice). Great bites and an ancient jukebox spinning vintage 45s just gild the lily.
201 E. Delaware Pl., 312-924-2531
Best new rooftop bar: You might be tempted to sit at the cool marble bar at the Raffaello Hotel’s handsomely appointed new cocktail lounge. But keep walking: The 1,500-square-foot terrace beckons. Built-in banquettes are tucked beside neatly manicured shrubbery, and sleek fire pits warm up the carousing as twilight unfolds. The best part is the feeling of hidden exclusivity: It’s just you and your friends at this lofty nook on the 18th floor of an unassuming boutique hotel.
Estate Ultra Bar
1177 N. Elston Ave., 312-582-4777
Best New Scenester Bar:The River North crowd has migrated west to this new destination that is within swimming distance of Goose Island. Spacious and offering great people-watching, Estate is attracting its requisite share of trend mongers and scene followers, mixed with relatively low-key partiers who just want to hang. And why not? The drinks are strong, the music is fun, and, as the location’s previous occupant taught us, life’s too short.
1725 W. Division St., 773-697-4804
Best New Sports Bar: During the game, only two things matter: clear sightlines and cold beer. But at halftime, we rally for all of the detail worked into this roomy Division strip destination, such as the bubble hockey table in the corner, some decent food (including an excellent turkey club), and the surprisingly extensive beer and cider lists. Two massive projectors offer the best viewing options in town, which means you’re winning–even if the Cubs aren’t.
3201 W. Armitage Ave., 773-252-9700
Best gin joint: Although technically it’s the only gin-centric bar in Chicago, we still want to give Scofflaw a prize for recognizing a need and filling it with flair. All cocktails at this Logan Square lounge are $8, sitting at the bar is rewarded with a gratis two-sip cocktail based on a forgotten classic, and bartenders are quick to offer samples to the adventurous from the dozens of bottles standing at attention on the lovingly rehabbed bar. (There are a number of alternatives for drinkers gun-shy from past, shall we say, gincidents.) Bonus: free cookies at midnight, warm from the oven.
2201 N. Clybourn Ave., 773-472-9920
Best retro lounge: Ignore the 30-somethings using their iPhones to Shazam the late-’60s soundtrack and order a second zombie at this roomy throwback bar on the western edge of Lincoln Park. The vibe is retro Vegas, right down to the remote-controlled enamel fireplace, smoke-mirrored tiles, and the red porcelain bathroom sinks. Cocktail prices are modern–most at $9–but you can swizzle-stick your way to a simpler time.
955 W. Fulton Market, basement
Best speakeasy: Getting into the city’s preeminent man cave is not actually as difficult as it might seem–insiders insist that if you ask the hostess at The Aviary, you’ll get in if there’s room. Which is not to say that you shouldn’t snap at the chance to sip the most accomplished libations in town for $20 a pop, splurge on oysters and caviar, and snuggle into the vintage leather couches. Your pocketbook will beg for mercy, but your ego will have the time of its life.
339 N. Dearborn St., 312-755-9463
Best wine class: No one goes to a recreational wine class to be cowed by snobs. Which is why we like Bin 36’s Bin School series. Led by the restaurant’s gregarious wine director, Brian Duncan, these topical evening seminars strike a comfortable balance between quaffing and chatting and serious grape talk. And since classes are held upstairs from William Hewitt’s kitchen, the palate-cleansing munchies are as delicious as the drinks.
2771 N. Lincoln Ave., 773-472-2771
Best whiskey bar: We like the pictures of old Dublin embedded in the bar at The Grafton, the compulsively readable cocktail menu at Longman & Eagle, the clubby elegance of The Gage, and the new rooftop deck at Fountainhead. But for a graduate seminar on the pleasures of imbibing whiskey, old-school is still the best school–at Delilah’s. Don’t be put off by the stygian darkness or the velvet Elvises: Instead, arrive in the late afternoon, eyeball the 400-plus whiskeys (including a house brand), and then ask the erudite bartender for a few suggestions. Listen, learn, sip–and repeat.
O’Hare International Airport, Terminal 3
Best airport wine bar: Apparently soft pretzels are out. O’Hare recently opened two wine bars in its push to spread the city’s foodie culture to its nation of bleary-eyed transients. Our pick? Bubbles, for its surprisingly well-secluded location off the main thoroughfare. The blue-lit lounge allows commuters to escape over charcuterie plates ($12) and a wine list that goes beyond a house red and white–plus, of course, Champagne. The ambiance gets extra pop from the grand piano, which can play on its own.
Chips and nuts at Bernard’s Bar
Best bar snacks: 11 E. Walton St., 312-646-1300