When the long day of networking comes to an end, it's time to relax and unwind. Fortunately, you're in one of the best American cities to do so. Chicago has a lively mix of clubs, theaters, bars and nightspots, many of which are the social epicenters of their neighborhoods. Add to these local favorites a generous number of sleek, chic trendsetters, and you have enough choices to create an unforgettable evening.
Here's some of the best nightlife we've found in Chicago, all accessible from McCormick Place and environs. Some are local hangouts, some are hidden dives and some are new arrivals. We've divvied them up by area, starting with the Loop, then moving north along the shore of Lake Michigan and inland. Cover charges, addresses and phone numbers are all included.
Although the Loop proper doesn't enjoy an abundance of nightclubs, it is home to the vibrant North Loop Theater District. The 76-year-old Goodman Theater recently moved to a glorious two-house complex (170 North Dearborn, 312-443-3800), and under artistic director Robert Falls, the Goodman offers productions of everything from experimental Shakespeare to Bertolt Brecht to James Baldwin.
On the Loop's commercial front, Broadway-in-Chicago textures color the shows at the Shubert Theatre (40 West Monroe St., 312-902-1500), the Ford Center/Oriental Theatre (24 West Randolph St., 312-782-2004) and the Cadillac Palace (151 West Randolph St., 312-782-1600). All three of these vintage theaters have been beautifully restored.
For the adventurous, there's a thriving off-Loop theater scene underway at such venues as the Steppenwolf Theater (1650 North Halsted St., 312-335-1650) and Second City (1616 North Wells St., 312-337-3992). Here you'll find cutting-edge ensemble theater, inspired skits and bizarro sketch comedy.
There are a few places in the Loop area to chill out and wet your whistle. One of the best is Buddy Guy's Legends in the South Loop (cover $5—$15, 754 South Wabash Ave., 312-427-0333). This downbeat, rec-room-type club is known for a stately approach to booking live local, national and international blues acts seven nights a week. The eponymous owner is a blues great in his own right—his wailing guitar influenced the likes of Eric Clapton and Stevie Ray Vaughan. It's best to arrive as early as you can, since the joint's popularity means that most general admission shows will sell out. As a bonus, the southern Louisiana kitchen serves better-than-average bar food.
Just down the street is Koko Taylor's Celebrity (cover $6—$10, 1233 South Wabash St., 312-566-0555), which also offers a steady diet of regional blues acts. Specials include an all-you-can-eat Sunday gospel buffet, and Thursday night is Ladies' Night, where women get in free. Once in a while, Koko, the "Wang Dang Doodle Diva" herself, will take the stage for a classic performance.
North Side/North Central
Part of a national chain of gay country-western clubs, Charlie's (no cover, 3726 North Broadway, 773-871-8887) is one of the friendliest clubs in the city, gay or straight. The place is large, dark and clean, and the huge dance floor (lit up by a giant mirrored boot) provides ample room for line dancing and major boot-scootin'. Late night (or early morning), a DJ throws in some progressive dance tracks to mix things up.
The Chicago Folk Center (cover varies, 4544 North Lincoln Ave., 773-728-6000), home of the Old Town School of Folk Music, is the nation's premier resource center for folk and world music. More than 3,500 students a week take classes here in eclectic subjects such as flamenco guitar, Bulgarian singing, Hawaiian hula dancing and more. The acoustically perfect concert hall was restored at a cost of $2 million (and christened with a Joni Mitchell show), and it's worth every penny. Concerts cover the whole field of folk, blues, and beyond, and regulars have included Guy Clark, Peter Yarrow and Charles Brown.
In a jazz-rich town, the Green Mill Jazz Club (cover $3—$8, 4802 North Broadway, 773-878-5552) is a hepcat speakeasy standout. The dark, seductive Mill first opened in 1907 and was restored to glory in 1986. Here you can groove out to top-notch local jazz artists and a steady influx of New York musicians who aren't heard anywhere else in the city. This is also the city's premier spot for late-late jam sessions.
Hala Kahiki (no cover, 2834 North River Rd., 708-456-3222) is the place for tiny bubbles—lots of them. The House of Pineapple, Chicago's biggest tiki bar and the only full-tilt South Seas establishment in the Midwest, has been here since 1967. Three dimly lit rooms, a blue fountain and a bamboo bar set the scene. Don't order beer, but do arrange for a cab or designated driver—the famous drinks pack a punch. Choose among beverages like the Dr. Funk of Tahiti, the Skip and Run Naked or the house favorite, the Zombie.
The Hideout (cover $5 or less, 1354 West Wabansia, 773-227-4433) is an urban roadhouse in the middle of nowhere, yet surrounded by everything. If Chicago is the capital of the nation's punky alternative-country scene, then the Hideout is the White House. A recent discovery of the edgy younger crowd, the bar has live alt-country playing in the comfortable back room. The Hideout is hidden in an industrial neighborhood, but any decent cabbie can find the place, and it's worth the hunt.
A neighborhood bar looking for a neighborhood, Marie's Rip Tide (no cover, 145 West Armitage Ave., 773-278-7317) is a dive par excellence. Here, people get ripped, slow-dance to the Sinatra-Elvis-Patsy Cline jukebox and contemplate each other in a driftwood world. It was once used as a set for the Crime Story TV series, and even the regulars slip off the slick vinyl barstools. No pretensions here, as this is a place where locals come to unspool their troubles into a few blue-collar rounds of red-eye.
In direct contrast, Metro (cover $5—$20, 3730 North Clark St., 773-549-0203) is an alternative concert venue with a major hipster attitude. There's moshing and body-surfing to be had in the concert hall upstairs, and a blue-hazed zebra motif distinguishes the downstairs Smart Bar. Music is the message here, as Metro has served as the launching pad for bands like Smashing Pumpkins and Urge Overkill. Even Axl Rose still hangs out here occasionally.
If you're a connoisseur of fine bubbly, head to Pops for Champagne (cover $6—$10, 2934 North Sheffield Ave., 773-472-1000). This classy and cleverly understated place is very elegant, but the easygoing staff and patrons prevent the atmosphere from getting intimidatingly exclusive. Vaulted ceilings, two-story windows and marbleized walls accent the cozy lounge. Be prepared for the prices—this is no cheap route—or peep at the finery and adjourn to the adjacent Star Bar for a more casual (and less expensive) evening.
Record Roundup (cover $3—$8, 2034 West Montrose, 773-271-5330) features stacks of wax, rows of vintage clothes and a live country hootenanny, all in what seems like a normal storefront setting. In addition to hawking thousands of nostalgic collectibles, this kitsch vendor also features live entertainment in a very informal arrangement (folding chairs!). In addition to music, you might also be treated to screenings of old TV commercials, cartoons or shows like Ranch Party with George Jones. It's also BYOB, so be sure to hit the beverage aisle before you delve into the weirdness.
At Slow Down—Life's Too Short! (cover $3—$8, 1177 North Elston Ave. at Division St., 773-384-1040), a big chunk of Key West has apparently floated north and lodged on the shores of the Chicago River. One of the most colorful bars in town, this place has three multilevel outdoor decks and a boat valet. Bob Marley fans and Jimmy Buffet devotees will feel right at home, and sports buffs can catch any game on the flotilla of TV sets. A free dessert is served before every meal as testament to the establishment's name and motto.
One of the city's hottest new dance clubs is Transit (cover up to $20, 1431 West Lake St., 312-491-8600), where a minimalist decor is right at home in a maximalist setting: this upscale dance house is part of a 10,000-square-foot complex. DJs deliver a heavy dose of funk and R&B with no surrender. The dense beats can boggle your mind, but the chic, dressy crowd seems to have no trouble maintaining their citizenship in the rhythm nation.
Weeds (no cover, 1555 North Dayton, 312-943-7815) is about cultural anarchy for a new beat generation. Poetry slams, jazz jams and rock bands compete with bizarre events like "Lawrence Welk Bubble Day" and "Birth Control Day." Old bras and other unmentionables hang from the ceiling of this bar run by former Chicago mayoral candidate Sergio Mayora, and most of the decor was salvaged from neighborhood dumpsters. Be prepared to rub shoulders with all manner of hell-raisers, hillbillies, chicks and tricks. A once-in-a-lifetime experience.
Party like it's 999 in the castle at Excalibur (cover $4—$9, 632 North Dearborn St., 312-266-1944). Over a hundred video games, pinball machines and pool tables appeal to your inner slacker, and the more industrious can visit Club X, the gigantic upstairs dance club. Or thrash your way to the adjacent Dome Room for regular heavy-metal infusions (you might get lucky and visit on "Bondage Night/Love Hurts," when ladies and couples in chains, handcuffs and leashes get in free). All this mayhem incongruously takes place in one of the few 19th-century Gothic buildings to survive the Chicago Fire.
The House of Beer (cover $3.50 or free, 16 West Division St., 312-642-2344) is a primo destination for brewsky aficionados and cigar chompers. One of the newest and most idiosyncratic spots on the city's most popular singles strip, it's designed like a north woods fishing tavern. An adventurous jukebox and 99 bottles of beer on the wall (literally) complete the escapism in this pocket of Wisconsiniana. Cab in if you can, as parking is in short supply.
Another of the Windy City's houses is the local branch of House of Blues (cover $10 and up for shows, 329 North Dearborn St., 312-923-2000), where there's live music seven nights a week. No American concert venue is booked with the variety and passion of House of Blues. The HOB (as locals call it) has featured performers like James Brown, Johnny Cash, Les Paul, Ted Nugent and Celia Cruz, just to name a few. Modeled after the Tyl Theatre opera house in Prague, the concert hall is the largest one in the chain, with 1,465 seats. Once you get over the fact that the "blues" in the name doesn't mean this is a blues bar, there's no reason not to have a great time.
Jilly's Bistro (no cover, 1007 North Rush St., 312-664-1001) is a posthumous tribute to Frank Sinatra's best friend and bodyguard, Jilly Rizzo. The cozy 100-seat nightclub is a splendid place for sophisticated conversation and a stiff drink. A seductive ring-a-ding-ding setting is accented with Sinatra and Rat Pack memorabilia hung on the walls. There's a separate downstairs disco, Jilly's Retro, that has a $5 to $10 cover, but for intense intimacy, stick with the Bistro.
For in-yo-face drinking and schmoozing, the best neighborhood tavern is The Lodge (no cover, 21 West Division St., 312-642-4406). This long-running singles-scene establishment on what locals call "the Street of Dreams" has held its own for decades against disco, punk and herpes. And its late-night license and one-to-one male-female ratio make it a popular stop for pro athletes winding down after a game. The charm comes in a shoebox-sized room resplendent in refined cedar and pseudo-antique paintings, topped by three tottering chandeliers regularly rattled by one of the loudest oldies jukeboxes in Chicago. Be prepared to belt out Meat Loaf's "Paradise by the Dashboard Light" if it comes up on the juke—it's a traditional Lodge sing-along.
The Old Town Ale House (no cover, 219 West North Ave., 312-944-7020) is a place for serious talk and serious drinks. Classic Chicago writers like Studs Terkel and Mike Royko used to pound a few here. The atmosphere is proudly sleazy (a word even the proprietors use), and this is as authentic as a Near North Side drinking experience can get. You'll run into artists, journalists, Second City actors and late-night waitresses and bartenders winding down after graveyard shifts.
And finally, for a truly unique club experience, there's Voyeur (cover $5—$15, 151 West Ohio Street, 312-832-1717). The hook is five closed-circuit monitors located throughout four cavernous rooms. Club-goers sit down on a sofa in front of a monitor connected to a joystick. They scope out a room by controlling cameras with the joystick, getting a 360-degree panoramic view of all their fellow nightclubbers. There's plenty of eye candy for the looking, either gettin' jiggy on the ample dance floor (where DJs spin erotic house, hip-hop, synth-pop and acid jazz) or splayed about on the other couches.
The Unofficial Guide to Chicago, 4th Edition was released in March. Unofficial Guides are published by Hungry Minds Inc.