Welcome back to the Pop 5, featuring Chicago's best places to do anything and everything. Last week, we wrapped up our Summer beauty series with the best spas in the city, and this week, we're moving on to one of my favorite subjects: cocktails! And we're not talking about your typical vodka-tonic. Nope, the cocktail craze has taken over Chicago, giving us lots of opportunities to indulge in a handcrafted, thoughtfully created libations, and — although it was difficult — we've narrowed it down to our five favorite spots to imbibe below.

  1. The Aviary (955 W. Fulton Market, 312-226-0868) isn't exactly classic, but the "cocktail bar, redefined" definitely serves up some of the most exciting drinks in the city. The bar-less cocktail kitchen creates drinks unlike anything I've ever seen: an old-fashioned is served inside an egg-shaped globe of ice (they cleverly call it "in the rocks" instead of "on the rocks"). Other highlights: the aged martini flight and a truffled Negroni (both shown right). If you're lucky, you'll be invited downstairs to the spot's speakeasy, The Office.
  2. Decades before the cocktail craze took over Chicago, The Matchbox (770 N Milwaukee Ave., 312-666-9292) was serving up classic drinks in its tiny, charming hall (seriously, it's small, so come early). Many drinks incorporate house-infused liquors; some favorites include the pineapple gimlet, a margarita rimmed in powder sugar, or any cocktail with a brandy-soaked cherry. Hit Matchbox while it's warm: outdoor seating means more opportunities to enjoy the classic drinks.
  3. Vintage-inspired Gilt Bar (230 W. Kinzie St., 312-464-9544) is sophisticated without being snooty, and the list of standard 1930s cocktails only adds to the throwback appeal. Enjoy a drink at the eight-person bar or head downstairs to Curio, Gilt’s underground cocktail lounge (or to its fantastic sister restaurant, Maude's Liquor Bar for an out-of-this-world, boozy smash).
  4. The Chicago speakeasy that kicked off the trend, The Violet Hour (1520 N. Damen Ave., 773-252-1500) has gained national recognition for the cocktail excellence that takes place within its purple-hued,1920s-inspired walls. You'll feel like you stepped into sexy old Southern mansion while you sip a painstakingly crafted cocktail like the Juliet and Romeo, Beefeater gin, mint, cucumber, and rose water.
  5. Sepia (123 N. Jefferson St., 312-441-1920) is known for its fantastic food and gorgeous interiors — the space was originally an 1890 print shop — but the libations at the charming bar are my favorite part of the Sepia experience. My pick: the French 75, with Hendrick’s gin, fresh lemon sour, orange bitters, and sparkling rose.

Source: The Aviary