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Nightlife

From legendary blues clubs and jazz venues to sleek martini bars and cutting-edge alternative music joints, the after-dark options in Chicago will satisfy any visiting night owl. Less style-conscious than New York or Los Angeles, the Chicago club scene has a friendly and welcoming reputation. Most bars close at 2am but can stay open an extra hour on Saturdays.

Live Music
Chicago offers a wide assortment of legendary blues and jazz clubs. Don't miss Kingston Mines (2548 N. Halsted St.; www.kingstonmines.com), a Chicago blues institution – open since 1968 – that encourages its patrons to "hear the blues, drink booze, and eat food" as late as 4am (5am on Saturdays); its two stages pump out the blues seven days a week. Blue Chicago (736 N. Clark St.; www.bluechicago.com) highlights female blues singers, and even hosts a Women's Festival every year on the second weekend of May. In addition to great live blues and impromptu acts by visiting rock stars, Buddy Guy's Legends (754 S. Wabash Ave.; www.buddyguys.com) offers a sizable collection of blues memorabilia on the walls and a tasty menu that includes shrimp Creole, jambalaya, and barbecue ribs.

An upscale jazz club, Green Dolphin Street (2200 N. Ashland Ave.; www.jazzitup.com) hosts all kinds of acts, from traditional jazz to Latin and big band. Open since 1947, The Jazz Showcase (59 W. Grand Ave.; www.jazzshowcase.com) has hosted the likes of Charlie Parker, John Coltrane, and Betty Carter; the jazz aficionados that frequent this joint don't appreciate talking over the sets.

Live alternative rock acts have had a home at Metro (3730 N. Clark St.; www.metrochicago.com) since 1982. Trent Reznor, Ministry, R.E.M., Liz Phair, Pearl Jam, The Smashing Pumpkins, Moby, the White Stripes, Fat Boy Slim, and the Yeah Yeah Yeahs have all cut their teeth in this old auditorium. Admission to Smart Bar, a basement dance club in the same location, is free with a ticket to a Metro show.

Bars
An assortment of late-night libations can be found in the River North Gallery District. Martini Ranch (311 W Chicago Ave., 312/335-9500) offers a dangerous collection of 40 different martinis. We don't advise that you try them all in one night, but we do recommend the mint chocolate chip martini—and trust us, one is enough! Bin 36 (339 N Dearborn; www.bin36.com) is a cavernous wine bar that also features a wine shop, wine academy, and bistro-style restaurant. The Motel Bar (600 W Chicago Ave.; www.themotelbar.com) features classic cocktails (Sidecars, Manhattans, and the Rob Roy) and kitschy decor. When stumbling out of a Cubs game at Wrigley Field, head across the street to the legendary Cubby Bear (1059 W Addison St.; www.cubbybear.com), voted the seventh best sports bar in America by Sports Illustrated. This 30,000-square-foot space features six bars and more than 100 TVs broadcasting every live sporting event imaginable.

PERFORMING ARTS
Chicago's other nickname, "Second City," seems apropos when comparing performing arts scene with that of New York City – but it's certainly thriving enough to come in a very close second. You can count on a booming theater scene, world-renowned symphony, opera, and dance companies, and free concerts under the stars.

From big Broadway-style musicals to intimate offbeat plays, dozens of great theatrical productions are hitting the floorboards every night. The Loop Theater District is home to several historic theaters of note, including the Chicago Theatre (175 N. State St.; www.thechicagotheatre.com), a beautifully restored 1920s landmark building that appeared in the finale of the movie-musical version of Chicago; the Ford Center for the Performing Arts (aka Oriental Theatre) (24 W. Randolph St.; www.broadwayinchicago.com), built as a movie palace in 1926; and the elegant Cadillac Palace Theater (151 W. Randolph St.; www.broadwayinchicago.com).

While the theaters in the Loop District tend to house large-scale Broadway productions, a number of internationally renowned "Off-Loop" theaters are known for exhibiting small high-quality productions. Showcasing new plays, neglected works, and established classics, the Steppenwolf Theatre (1650 N. Halsted St.; www.steppenwolf.org) has been a pioneering force in Chicago theater since it being co-founded by Gary Sinise in 1974; Sinise, along with longtime ensemble members John Malkovitch, Joan Allen, and John Mahoney, still act in productions today. Located on the Navy Pier, the Chicago Shakespeare Theater (800 E. Grand Ave.; www.chicagoshakes.com) focuses on presenting works by the bard. If you're looking for a laugh, The Second City (1616 N. Wells St.; www.secondcity.com) is an improv sketch comedy company famous for launching the careers of John Belushi, Bill Murray, Gilda Radner, Chris Farley, and Stephen Colbert.

The League of Chicago Theatres offers half-price, day-of-performance tickets to more than 150 Chicago area venues through its HotTix (www.hottix.org) program. Dozens of shows are listed each week, but you must purchase tickets in person at various HotTix locations (Tues–Sat 10am–6pm & Sun 11–4pm; closed Mon): the Loop (72 E. Randolph St.), the Magnificent Mile (WaterWorks Visitor Center, 163 E. Pearson St.), and the North Shore Center for the Performing Arts (9501 Skokie Blvd., Skokie).

The Lyric Opera (20 N. Wacker Dr.; www.lyricopera.org), located in the gloriously renovated art deco Civic Opera House, attracts some of the world's best singers for its lavish productions. The season runs from September through March. The Chicago Symphony Orchestra (220 S. Michigan Ave.; www.symphonycenter.org) performs over 200 concerts a year at Symphony Center. The Joffrey Ballet (www.joffrey.com) performs innovative dance pieces at the Louis Sullivan-designed Auditorium Theatre (50 E. Congress Pkwy.; www.auditoriumtheatre.org) and various other locations throughout the city.

In the summer months, nothing is more magical than a free concert under the stars with the Chicago skyline as a backdrop. The Grant Park Music Festival (www.grantparkmusicfestival.com) is a free concert series showcasing the Grant Park Orchestra and Chorus and a variety of ensembles and musicians at Millennium Park's Jay Pritzker Pavilion (55 N. Michigan Ave.). The ten-week season opens in mid-June and runs through late August.

See Chicago Travel Guide