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3154 West Diversey Avenue Pro tip: Don't skip the banana daiquiri. There's just enough fantasy-Martinique wallpaper, staff in tropical shirts, a graphic, kitschy menu-but the real transportation happens in the glass, with the intricate play of a broad spectrum of rums and fresh juices. Cofounded by Paul McGee, who is behind many of the city's great watering holes (including Milk Room, above), Lost Lake is one of the best in the country. If you've ever experienced winter in Chicago, you understand the need for the escape of a great tiki bar. 12 South Michigan Avenue Where to crawl next: The Cherry Circle Room around back for a burger and a manhattan. A 1927 Old Hermitage sour-mash whiskey had a whiff of funk and an uncanny roundness-this is what history tastes like. The Campari and Fernet from the '70s that are used in some of the cocktails are gentler-modern versions use extracts not so much back then, the bartender tells me. Milk Room is a tiny altar to the heady, rarefied world of vintage spirits and amaros.
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It hits you full on when you take one of the eight seats at a bar discreetly tucked behind a wall of stained-glass windows and sip something decades or even a century old. The Venetian Gothic woodwork in the Chicago Athletic Association hotel lobby sets up that they-don't-make-'em-like-they-used-to feeling. What Kevin sipped is gone but not forgotten. 1057 Atlantic Avenue What you're (also) having: The deliciously dirty steakhouse martini. As if the food truck and colorful Miami-meets-Cali-in-a-former-Brooklyn-auto-body-shop ambience didn't clue you in. The drinks are just as good, but the vibe is much more chill. That's the frozen, slushy-machine version of the internationally famous, de facto Serious Cocktail Person calling card that is the Penicillin, a smoky mix of Scotch, honey, and ginger created by co-owner Sam Ross at Milk & Honey, the original Serious Cocktail Person bar. Kevin Sintumuang falls for casually proper cocktails. 423 East Kirkwood Avenue What you're having: Nothing fancier than a Bud. I aspire to it still, though, and make it back to Nick's about once a year, decidedly grayer, wiser. I left Bloomington soon after I turned twenty-three, never making the Bucket Brigade. I think you have to inherit a bucket you certainly couldn't buy one. Nick's is known for its Bucket Brigade, which hangs over the bar and is the ultimate in privilege-instead of downing ice-cold Buds in frozen mason jars, you sit down and have your own pail, with your name on it. On nongame nights, the crowd is decidedly grayer, wiser, and more old-fashioned. It's a sports bar, sure, in a varnished, waxy way-you walk in and (aside from the big screens) it could be 1958, with "Branch" McCracken's Hurryin' Hoosiers still playing ball. Dating from 1927, it had an allure that hinted at something more seasoned than the frat bars, live-music venues, and degenerate pool halls I frequented. Nick's was the first bar I considered aspirational. As the neon sign in the window will tell you, "You earned it." 75½ Rainey Street Where to crawl next: Craft Pride down the block for beers and Detroit pizza.
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Or call for the Medicina Latina, which mixes tequila, mezcal, ginger, and lime to cure what ails you.
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Prop an elbow on the padded bar and watch your cocktail materialize from the fresh ingredients cooling on ice. Your best bet is this little blue bungalow, whose name pays homage to the Grateful Dead song. Today the colorful houses on this half-mile stretch play host to the city's hippest drinkers and favorite local bands. Ten years ago, Rainey was just another sleepy residential Austin street.