Pick your poison

Vodka
Gimlet at Matchbox (770 N Milwaukee Ave at Ogden Ave, 312-666-9292). When it's done right, a vodka gimlet tastes like a melted key-lime sorbet. When it's done wrong (read: crapload of Rose's, well vodka, tons of ice), it tastes so acidic you can almost feel it burning a hole in your liver. Here's why bartenders at Matchbox, a sliver of a bar in West Town, do it right: They mix together freshly squeezed lime juice, egg whites and vodka, and serve it straight up in a martini glass rimmed with powdered sugar—a bargain at $6. Celebrating its tenth year in its current incarnation (owner David Gevercer bought it from a 94-year-old man who had run the place since 1930), the bar attracts a loyal neighborhood crowd that squeezes onto 20 stools for postwork cocktails and weekend benders.
Lychee martini at Rodan (1530 N Milwaukee Ave between North Ave and Honore St, 773-276-7036). With its fragrant, juicy, translucent flesh, eating a lychee can be a nearly sexual experience. Restaurant/lounge Rodan, a sleek hipster hang in Wicker Park, has condensed the seductive powers of the tropical fruit into a potent martini ($7.50). Made from vodka, lychee juice, a dash of pineapple juice and pineapple rum, this strong drink is a not-too-sweet alternative to the passe Cosmo. Wasabi tempura-battered fries from the late-night kitchen are a perfect accompaniment. The South American–influenced Asian food at Rodan is tasty, but we'd sip this stunner if there were nothing to chew on here but straws.
Bloody Mary at Nisei Lounge (3439 N Sheffield Ave at Newport Ave, 773-525-0557). The name of this Wrigleyville spot refers to second-generation Japanese-Americans—but you won't find sushi and scenesters here. A recent makeover has elevated Nisei from its semi–dive-bar status, but the low-key neighborhood vibe remains. Most folks swill beers, but the Bloody Mary ($7) is arguably the best in town. Each bartender has his own recipe, but if Dan's working, expect a fiery, classic interpretation, spiked with celery salt, Worcestershire sauce and Tabasco (or horseradish, if anyone's been to the store lately). It's topped with a floater of Guinness and served in a pint glass with a green olive and lime garnish.
Puffer's Passion at Puffer's (3356 S Halsted St between 33rd Pl and 34th St, 773-927-6073). After we've stuffed our faces with the best Polish sausages around and downed pricey beer at the Cell while cheering on the Sox, we're too pumped to end the night. So we head for this Bridgeport favorite, where the owners not only keep a great selection of brews on tap, but woo the fruity-drink crowd with this mix of peach vodka (Stoli or Absolut), orange and cranberry juices, and lemonade ($5). The crowd of South Side lifers are a fairly friendly bunch, and the bartenders are generous with free rounds, but if you dare wear Cubs gear, you're on your own.
Wild Berries at Fulton Lounge (955 W Fulton St at Morgan St, 312-942-9500). Pigeonholing Fulton Lounge as a bourgeois scene for the martini set is easy. It's in the meatpacking district, and it has a velvet rope. But once you get past the doorman, this place has one of the most laid-back, friendliest vibes in town. And once you try the Wild Berries ($8)—a subtly sweet-and-sour combo of Absolut Currant, wilderberry Schnapps and sour mix garnished with fresh berries—you may just become a martini person yourself.

Rum
The Summer Drink at Celebrity (1856 W North Ave between Honore St and Wolcott Ave, 773-365-0091). A slave to the seasons, Celebrity recently gave itself a summer makeover (more like a quick changeover, considering it's less than a year old). But we love the new look: The dark burgundy walls were repainted a mossy-green, the candles were replaced with plants, and the bar opened its doors onto an Astroturf-carpeted sidewalk patio. A summer cocktail list was rolled out to fit the new digs, and of the ten new drinks it featured, the aptly named Summer Drink ($10) is the best. The fresh, aromatic, mojito-ish concoction combines muddled fresh mint, limes and sour mix with Bacardi Limon and a splash of Corona to give it a little fizz.
Mai tai at Trader Vic's (17 E Monroe St between State St and Wabash Ave, 312-917-7317). The '40s and '50s craze for all things Polynesian left behind some great stuff, most of which will run you big bucks on eBay. But in potable form, we have the mai tai ($8), a paper parasol–decorated frozen rum drink that was purportedly invented in '44 by Trader Vic's namesake creator, Victor Bergeron. The drink's Tahitian name translates as "out of this world" and, while we might not go that far, we can see how you might forget you're in Chicago if you sit and sip these for an hour or two in the basement of the Palmer House Hilton. The frosty blend of dark and light rums, Cointreau, almond syrup, lime juice and grenadine is topped with a sprig of mint, lime, pineapple wedge, cherry and a bright umbrella. You'll only feel like a dorky tourist for about five minutes, and then you shouldn't feel anything at all.
Strawberry colada at Hala Kahiki (2834 River Rd, River Grove, 708-456-3222). It shouldn't come as a surprise that this tiki bar serves up mean rum potions, but which to order when you're faced with the multipage menu? We sampled our way under the table and found that while the Scorpion hit us the hardest, the tropical strawberry colada ($6.75) tasted the best. Plenty of dark rum is blended with fresh strawberries, coconut milk and pineapple juice, and topped with whipped cream and a plump strawberry. Sit back and sip it in the thatched bamboo-laced maze of dim indoor rooms or head outside to the lush patio, where you'll be surrounded by slick, newly arrived 22-year-old Russians who are apparently enamored with this iconic slice of '50s America.
Planter's Punch at Fizz (3220 N Lincoln Ave between Melrose St and Belmont Ave, 773-348-6000). It's no tiki hut, but this Lakeview spot turns into an island getaway every week on Waikiki Wednesdays, when the sports bar, full of dark wood and frat boys, goes Caribbean for the night. On the menu of classic rum drinks like pina coladas and mojitos is one cocktail that's simply just too gimmicky to resist: the Planter's Punch ($11). Don't get us wrong—there's nothing wrong with punch, and the Planter's mix of rum, grenadine, and orange and pineapple juice is a classic (its sketchy origin dates to the mid-1800s). But Fizz pours it into a "Volcano bowl," a large ceramic cup with a small "volcano" in the center, where cheap rum is set on fire, creating a flame that blazes while you sip away on extra-long straws (to keep you from setting your nose on fire). The folks at Fizz say it's for two, but, come on—it's punch for crying out loud! You can take it down yourself.

Tequila
Margarita at Mondelli's (7 E Oak St between State and Rush Sts, 312-266-7362). A good margarita should beautifully balance sweetness with tartness, quench the thirst that results from eating salty foods and never, ever be garnished with an umbrella. Unfortunately, a good margarita is hard to find. So we tracked down the margarita at Mondelli's, a bar that uses headshots of celebrities like Tony Danza and Jerry Springer (well, they were once celebrities) to paper the walls and attracts a crowd of shoppers and tourists alike. Rimmed with rock salt, this perfectly balanced and simple 'rita ($6) goes down splendidly with a handful of free popcorn and people-watching on Oak Street.
Beergarita at Crew (4804 N Broadway between Lawrence Ave and Gunnison St, 773-784-2739). The beergarita ($6) comes out of a tap like a beer, but it's really a mixture of suds, tequila, lemon soda and salt. The result is a brew that's dressed up like a cocktail, served over ice in a pint glass and perfect for drinking on the sidewalk patio. It tastes kind of like beer without the heaviness, Sprite without the sickly sweetness and tequila without the sting. In other words, it's hard to pin down. What else would you expect the football-and-Cher–loving clientele at a gay sports bar to drink?
Gran Paloma at Salud (1471 N Milwaukee Ave between Honore St and Evergreen Ave, 773-235-5577). If Salud was trying to impress us with size, the huge tequila list at the year-old Wicker Park lounge did the trick. The variety will likely confuse even an agave geek, so if you're not into sipping big-buck pours, go for this blend of blanco tequila, grapefruit juice, fresh lime juice and a splash of Squirt soda. Most weekends, you'll drink this take on the 'rita ($9) elbow-to-elbow with twentysomething singles looking for the tequila to do the talking. If you want a bit of privacy, come early during the week, when you can grab an illuminated table and order a couple of Mexican munchies.
El Corazon at Nacional 27 (325 W Huron St between Orleans and Franklin Sts, 312-664-2727). There's something about this Pan-Latin spot that sets the perfect mood for sipping this fresh and fruity passion-pom 'rita ($11.50). The good-looking pros behind the bar shake Corzo Silver with pomegranate and passion fruit juice, add house-made sour mix, and pour the finished drink into a glass rimmed with sea salt and crushed Tellicherry peppercorns. Order one to linger over during the 11pm weekend "shift," when the venerable restaurant seamlessly morphs into a sexed-up dance club for all ages and all races, courtesy of Latin DJs who remix past and present salsa and merengue.

Gin
Cucumber Fresco at Wave, W Chicago Lakeshore (644 N Lake Shore Dr between Ontario and Erie Sts, 312-255-4460). Face it: A crunchy slice of cucumber has displaced the lemon or lime wedge as the hip cocktail garnish. And nothing embodies this trend better than the cool, ultra-refreshing Cucumber Fresco ($9) at Wave, the W Chicago Lakeshore hotel's chic watering hole. The drink combines two of our favorite spirits—Pimm's and Hendrick's Gin, both of which are traditionally garnished with a slice of cuke—with fresh lemon juice, muddled cucumbers and sugar.
Singapore Sling at Motel (600 W Chicago Ave at Larrabee St, 312-822-2900). It's easy for a bar to latch onto the classic cocktail trend, but the proof is in the glass. We put this hot new River North spot, which serves old-fashioned favorites in a retro-hip setting, to the test and tried everything from its Harvey Wallbanger to a Pink Lady. Our favorite is the Singapore Sling ($8), a concoction nearly identical to the original 1915 version created at Singapore's Raffles Hotel. The kitchen-sink combo starts with a hefty pour of Hendrick's Gin, then adds Cointreau, B&B (Brandy & Benedictine), pineapple and lime juices, grenadine, bitters, and club soda. Take it outside to the patio to enjoy the weather or to the back of the joint to down while shooting pool.
Dark Fantasy at HotHouse (31 E Balbo Ave between State St and Wabash Ave, 312-362-9707). We've had many a Dark Fantasy ($9) at the HotHouse, and you can take that however you wish. But when it comes to the drink, we're talking about a Bombay Sapphire gin martini, sweetened up with Mathilde Framboise (raspberry liqueur) and pineapple juice, shaken and poured into a sugar-rimmed glass. Seems like the perfect drink for a nonprofit music and performing-arts nightclub, where social action and artistic expression collide, and an intoxicating blend of world and experimental music reigns on the stage. Who says you have to sip ginseng tea to change the world?

Whiskey
Manhattan at Bungalow Lounge (1622 W Belmont Ave between Ashland Ave and Paulina St, 773-244-0400). At most bars, order a Manhattan and you'll get a highball filled with ice, a splash of cheap whiskey, a half cup of vermouth and a couple of cloyingly sweet maraschino cherries. But Lakeview's Bungalow gives this classic cocktail the respect it deserves. Starting with top-shelf bourbon, a splash of vermouth and bitters, the drink ($9) is shaken lightly and poured into a martini glass, and finished with brandy-soaked cherries and—the secret ingredient—a bit of the brandy the cherries have been soaking in. After two, you'll be knocked straight on your ass, but if you were smart enough to reserve one of the intimate booths lining this Prairie Style room, at least your posterior will land on cushy leather.
Wooden Leg at Hideout (1354 W Wabansia Ave between Willow and Ada Sts, 773-227-4433). If you know anything about rye whiskey, you know it's purely American. And though even George Washington used to make the strong stuff, its popularity never quite recovered after Prohibition, making it hard to find aside from at die-hard honky-tonks. Now, we're not saying you're going to find beer-gut bikers busting bottles over heads, but this hidden little roadhouse is Chicago's hub for alt-country, and a great place to have a drink. Crooner Kelly Hogan has tended bar here off and on over the years, and we say her biggest contribution (aside from great live performances) is the Wooden Leg ($4), a blend of rye, soda, bitters and lemon juice. Peg leg or not, you're sure to walk crooked after a couple.
Fuji Apple at Mirai (2020 W Division St between Damen and Hoyne Aves, 773-862-8500). Okay, so technically it's a sushi restaurant, not a bar, but don't tell that to the throngs of pretty people lounging around the plush upstairs meet-and-drink spot. When proprietor Miae Lim named this five-year-old splurge spot "Mirai" (Japanese for "future"), she hit the nail on the head. This martini ($10) combines Maker's Mark with Ozeki sake, apple liqueur, orange juice and sweet-and-sour. Plenty potent but fruity enough for sake virgins, it beats the pants off beer-based sake bombs.

Wildcard
Pisco Sour at SushiSamba Rio (504 N Wells St at Illinois St, 312-595-2300). The Chicago outpost of the New York sizzler that claimed Carrie and crew as regulars on Sex and the City opened two years ago. And this summer, word is spreading that its rooftop patio is one of the nicest upscale outdoor spots in town. The wine and sake list are tempting, but go for this hard-to-find South American cocktail ($10). Pisco, a Peruvian brandy distilled from white muscat grapes, tastes something like a cross between whiskey and tequila. In this classic combo, it's added to blended egg whites and sugar, given a hefty dose of fresh lime juice, a splash of bitters and poured over ice.
Caipirinha at Tiny Lounge (1814 W Addison St between Wolcott and Ravenswood Aves, 773-296-9620). When we discovered this spot many benders ago, it was empty, save for a trio of construction workers having an after-work beer next to hipsters exploring the incongruous nook in the shadow of the Brown Line tracks. With Art Deco–inspired flourishes and a fancy-pants martini list, it was a tad ahead of its time. But now that the 'hood's caught up, you'll have to ask someone to move an adorable little pink designer purse if you want to sit. Fortunately, cocktails are still painstakingly assembled by hand. Our favorite is the caipirinha ($6.80), in which a handful of lime slices are mulled with sugar and a splash of simple syrup, then topped with cachaca, a rustic, rumlike Brazilian spirit distilled from sugar cane. Poured into a rocks glass that's rimmed with chunky raw sugar and packed with hand-crushed ice, it's the best grown-up snow cone around.
Continental at Bar Thirteen (1944 W Division St between Damen and Winchester Aves, 773-394-1313). Somewhat slick and packed to the gills most weekend nights, this Wicker Park spot straddles the fence between bar and club. Mixologists have concocted more than two dozen "Thir-tinis" for a hip, ready-to-spend crowd drawn in by rotating DJs who specialize in that house/hip-hop blend that evokes more head-nodding than ass-shaking. When we feel like flexing our pimp muscles and ordering up some Hennessy, we forego a snifter and go for the tasty Continental ($10), a martini made by shaking the cognac with cranberry juice and a splash of grapefruit.
Doctor's Delight at Cotton Club (1710 S Michigan Ave between 17th and 18th Sts, 312-341-9787). This South Loop jazz club's fruity signature drink ($7) is pre-mixed by "Dr. Nazon," a friend and regular of the bar. It's an all-natural health drink, but most customers do their own doctoring, adding a shot of HPNOTIQ, a fruit-infused cognac (though pretty much any booze will do the trick). The good doctor's recipe is top secret, but we were able to wheedle a few ingredients out of him: ginseng root extract, and aloe vera, apple and lemon juice.
Pomegranate Spritzer at Uncommon Ground (3800 N Clark St at Grace St, 773-929-3680). Leave it to Uncommon Ground to make a cocktail that's actually good for you. The patrons at this smoke-free lounge and roots music venue definitely know how to have a good time; they just don't want to kill themselves doing it. Enter the Pomegranate Spritzer ($7), a combination of soda water (harmless), lime (vitamins!), pomegranate juice (full of antioxidants) and sauvignon blanc (French doctors are always telling us to drink at least a glass of wine a day, right?). And you thought wine spritzers weren't cool.