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Chicago Nightlife

The Aviary
955 West Fulton
Chicago , Illinois

If you can't snag a table at Grant Achatz's Next restaurant (and you can't if you don't buy a ticket online, far ahead of time), the second best thing sits right next door at The Aviary, the dinner theater's sister cocktail bar cum lounge. Taking the fashion for designer molecular cocktails to Achatz-worthy heights, this plush sanctuary features a vigilant doorman, concierge-like waiters, high-backed semicircular banquette pods, and lots of moony couples. The Bites menu is true to its word. These thumb-size dishes are very tasty (try the crab with avocado, mango, and almond), but the tab can run up quickly. However, it's the zany cocktail concoctions that are the big attraction, from a palette-rousing Huckleberry (that's lemon, Thai long peppercorn, and gin) to the Sweet Potato (orange, tequila, and smoked paprika). There is also a basement speakeasy, available for private parties, but The Aviary's biggest perk may be a simple one: A limited number of reservations are actually possible, if you follow orders and email in your request at precisely 6, 8, or 10 pm.—Raphael Kadushin

Big Chicks
5024 N. Sheridan Road
Chicago , Illinois
Tel: 773 728 5511

Don't be fooled by the name: This unpretentious uptown bar caters equally to lesbians, gays, and straights of all sizes (many are students from nearby Loyola and Northwestern). The narrow main room is awash in red light and decorated with artwork—some of it by extraordinary artists like Diane Arbus—featuring women in various stages of undress. (It's the personal collection of owner, and namesake big chick, Michele Fire.) Bartenders pick the tunes during the week, but DJs take over on the weekends, and the side room, called the Salon, morphs into a dance floor. Though there's no food served (except on Sunday afternoons), Fire's organic restaurant, Tweet, is right next door and open through dinnertime most evenings.

Open Mondays through Fridays 4 pm to 2 am, Saturdays 3 pm to 3 am, Sundays 10 am to 2 am.

Billy Goat Tavern
430 N. Michigan Avenue
Chicago , Illinois
Tel: 312 222 1525

The classic Saturday Night Live skit where native Chicagoan John Belushi played a harried Greek line cook—shouting, "Cheezborger, cheezborger, cheezborger. No Pepsi. Coke!"—brought this Chicago institution (which the skit was based on) to national fame in the late '70's. But it's been a local landmark since its original owner, William Sianis, was forbidden by the Chicago Cubs management from bringing his house goat—yes, a real live goat—to Wrigley Field during a 1945 World Series game. Located across the street, and practically beneath, the stately Tribune Tower on a gloomy stretch of Lower Michigan Avenue, the place is immensely popular with tourists. Even so, it's still a haunt for local reporters and advertising execs, and it still serves good, greasy cheeseburgers on fluffy buns. Take time to peruse the yellowed newspaper clippings and Hall of Fame photos that decorate the walls—they're a crash course in Chicago history.

Open Mondays through Fridays 6 am to 2 am, Saturdays 10 am to 3 am, Sundays 11 am to 2 am.

Chicago Blues

Chicago blues music is justifiably famous; some of the best-known living blues performers—including Buddy Guy, Howlin' Wolf, Koko Taylor, and Junior Wells—cut their teeth in the music clubs here in the '50s and '60s. These days, there are still plenty of places where you can catch top-notch blues acts.

Downtown, you can get two clubs for the price of one at Blue Chicago's two locations. The Blue Chicago store holds an all-ages set every Saturday. On the South Side, Buddy Guy's Legends presents live blues acts seven nights a week. In Lincoln Park, bands play on two stages till 5 a.m. Sunday morning at Kingston Mines, one of Chicago's largest clubs, with the tagline "Hear blues, drink booze, eat food".

The annual Chicago Blues Festival, the largest free-admission event of its kind, attracts 750,000 fans to Grant Park each June.

Green Mill Cocktail Lounge
4802 N. Broadway Avenue
Chicago , Illinois
Tel: 773 878 5552

If we had to pick one place in all of Chicago that epitomizes the city's rich and gritty history, it'd have to be the Green Mill. Al Capone used to hang out here in the 1920s, when it was a speakeasy during Prohibition. Then and since, the smoky, dark-wood-paneled, and dimly lit joint has been one of the best places in the country to see every flavor of jazz—Dixieland, traditional, bebop, contemporary, progressive, you name it—by local and legendary outfits alike. The seasoned bartenders are consistently cranky and it's elbow-to-elbow by 8 p.m. most nights, so get there early and snag a booth opposite the bar—it's the best spot to see and hear the music but still be able to have a (hushed) conversation. As it has since 1986, every Sunday night the lounge hosts the fabled Uptown Poetry Slam.

Open daily noon to 4 am.

1354 W. Wabansia Avenue
Chicago , Illinois
Tel: 773 227 4433

Finding this aptly named bar can be a major challenge. Don't even attempt to take public transportation here; just get in a cab (your taxi driver will know where it is) and look for the glowing "Old Style Beer" sign that's a beacon of light in this warehousey no-man's-land. It's quite literally a hole in the wall: Faded beer cans rust on the windowsills, and the backroom "lounge," with its thrift store–quality furniture and makeshift "stage," feels more like a college dorm room than a bar displaced Chicagoans get all misty-eyed about. But the legendary place is also ground zero for the city's fertile alternative country/postpunk music scene. There's live music every night; local outfit Devil in a Woodpile plays a raucous mix of ragtime, acoustic blues, and jug tunes with no cover charge every Tuesday. If members of your party prefer fancy drinks, head elsewhere; there's a limited selection of spirits here. Cans of PBR, however, are a mere $2 (and worth every penny).

Open Tuesdays 7 pm to 2 am, Wednesdays through Fridays 4 pm to 2 am, Saturdays 7 pm to 3 am.

I.O. Theater
3541 N. Clark Street
Chicago , Illinois
Tel: 773 880 0199

Formerly called the Improv Olympics, the I.O. is the city's "other" famous comedy club (it plays second fiddle to the better-known Second City). Upstairs you'll find stadium seating in the Del Close Theater, where the set shows are performed, while downstairs, the Cabaret Theater's tables have room for around 100 people. It's here you'll find the improv for which the club is famous. The experience here is far more intimate than at Second City; you feel like you're practically on stage with the comedians. Drinks and pizza are available in both theaters.

Performance times vary; call ahead.

Map Room
1949 N. Hoyne Avenue
Chicago , Illinois
Tel: 773 252 7636

Owners Mark and Laura Blasingame have two passions in life—traveling and beer— and their cozy pub is a showcase for both. The giant map of the world covering the walls and the library of National Geographic magazines (which fills several dilapidated bookcases) are impressive, but the beer selection is what really sets it apart. Belgian and regional brews are the specialties; in addition to the 250 bottled beers offered, 27 are always on tap, one of which is cask-conditioned, stored in its own cooler, and served in the old-school manner via hand pump. Sunday night is movie night, and Tuesday is international night, with a free dinner buffet (with a two-drink minimum) catered by neighborhood restaurants.

Open Mondays through Fridays 6:30 am to 2 am, Saturdays 7:30 am to 3 am, Sundays 11 am to 2 am.

Rockit Bar and Grill
22 W. Hubbard Street
Chicago , Illinois
Tel: 312 645 6000

As advertised, the latest offering from local nightlife maven Billy Dec and his savvy band of successful associates (together they have given Chicago several of its hottest clubs, including Le Passage, The Bedroom, and The Dragon Room) really is a bar and grill, albeit a Western-inspired and upscale one. Designed by local celeb interior decorator (and Oprah chum) Nate Berkus, the backdrop has comfy ambience that feels simultaneously rustic (antler chandeliers and tree-stump tables) and modern (flat-screen TVs). You may spot David Schwimmer or Jeremy Piven shooting stick upstairs, but more likely you'll find a well-heeled crowd downstairs noshing on French-inspired cuisine like lamb hot pot with radicchio or chicken paillard. A modified late-night menu is served until 1:30 a.m., but it can get too loud and crowded to think about eating after 11, especially on weekends.

Open Sundays through Fridays 11:30 am to 1:30 am, Saturdays 11:30 am to 2:30 am.

3356 N. Halsted Street
Chicago , Illinois
Tel: 773 281 3355

Of the dozens of predominantly gay bars that line North Halstead Street in Boys Town, Roscoe's is neither the glitziest nor the coziest. It is, however, one of the friendliest, and—with six separate bars, a good-sized dance floor, and a beer garden out back—quite possibly the biggest. If the main bar is too noisy and crowded, look for a place to sit near the pool table or one of the smaller, lower-key lounges (one of which has a fireplace). The drinks are nothing special—20 predictable beers on tap, and your usual array of frozen cocktails—but the weekly parties are: Mondays and Wednesdays are karaoke nights, Tuesday is "Drag Race" night, and Sundays are "Male Call," with a smorgasbord of flirting games. DJ-spun Top 40 fuels the popular weekend dance parties, and the delightfully raunchy wet-boxer-shorts contest still packs 'em in the last Thursday of each month.

Open Mondays through Fridays noon to 2 am, Saturdays 11 am to 3 am, Sundays 11 am to 2 am.

Second City
1616 N. Wells Street
Chicago , Illinois
Tel: 312 337 3992

If you only go to one comedy club in your life, this should be it. Yes, you'll find Second City franchises scattered about the country, but there's no matching the original. A perusal of the framed photos in the foyer is a who's who of funny: Dan Aykroyd, Gilda Radner, John Candy, Steve Carrell, Stephen Colbert, Mike Meyers, and Amy Sedaris are just some of the comedians who started their careers here. The casual main theater—officially called "The Second City Mainstage"—seats 290 and is as classic as comedy clubs get; you'll likely be seated randomly at a table and plied with drinks and appetizers until the show begins. Big names and alums still perform here periodically, but both the Mainstage and Second City e.t.c. (a smaller, second stage) have resident troupes that write and perform original comedy revues.

Performance times vary; call ahead.

Vic Theater
3145 N. Sheffield Avenue
Chicago , Illinois
Tel: 773 472 0449

In the early 1900's, the Vic was the Victoria Theatre, a five-story vaudeville house. These days, the intimate venue (it holds up to 1,400) is looking its age, but the Italian marble of the lobby floor and staircases still impresses, and the original wall sculptures of plants, vines, and female faces have been restored. More importantly, the acoustics are as good as ever, and it remains one of the city's best places to catch hot local acts and national performers from David Bowie to Nanci Griffith. When live shows aren't scheduled, the venue transforms into a movie theater for its popular "Brew and View" nights, when second-run and cult classic films are screened, and the well-lubricated crowd can be quite talky.

The Violet Hour
1520 N. Damen Avenue
Chicago , Illinois
Tel: 773 252 1500

This posh Wicker Park lounge is the place for a hip, dressy night on the town. The unmarked door recalls a speakeasy, the name (a line from T. S. Eliot's The Waste Land) suggests romantic drama, and the interior follows suit. Designer Thomas Schlesser (the man behind Avec and Blackbird) took a break from his signature pared-down style and opted for velvet drapes, high-backed blue chairs, and crystal chandeliers. The surprisingly ambitious canapé menu includes duck meatballs and fried banana, but make sure to leave room for the Violet Hour's raison d'être: cocktails, painstakingly prepared—at times with an eyedropper—by the in-house mixologists.

Open Sundays through Fridays 6 pm to 2 am, Saturdays 6 pm to 3 am.

Information may have changed since the date of publication. Please confirm details with individual establishments before planning your trip.