Chicago is known as the Second City from the days when it was the second largest city in the U.S., but it’s second to none when it comes to music. Whether you’re taking in jazz from a booth where Al Capone once held court, or dancing to a free brass band concert in an soaring outdoor pavilion, Chicago’s musical diversity will make it your kind of town.
Venues that Rock
Chicago’s overcrowded Rush Street club scene was captured in the movie, “About Last Night,” but for a night that’s easier on the ears and wallet, head to locals’ favorite music venue Schubas Tavern instead. The former Schlitz Brewery in Wrigleyville (near The Cubs’ Wrigley Field) offers no-cover nights for popular local bands, often on Mondays. A reasonably priced $15 cover for national indie bands, and $4 draft beer adds to the draw. If you’re a brew-o-phile, try a pull of Illinois brewery Tocayo’s White Hominy Ale.
Catch a concert or comedy night at the Near North Side’s classic art deco venue Park West for a range of acts, from singer/songwriter Shawn Colvin to comedian W. Kamau Bell to Metallica played by four cellos. Eclectic bookings with solid acoustics play to the room’s capacity of 900. Book a booth, and the table service will keep you from having to squeeze through the crowd on a sold-out night. The slightly larger Northside venue Metro has been popular since the early days of Chicago’s own The Smashing Pumpkins in the late ’80s. The bar is cash-only, so bring your own or hit the club’s ATM. Join locals on the dance floor at the basement-level Smart Bar.
Chicago Blues in the Night
Chicago’s blues icon Buddy Guy holds court at his namesake club Buddy Guy’s Legends on the South Side when he’s not touring. Round out a night of blues with a full slab of baby back ribs for something to write home about. Back on the North Side, the funky and intimate Blue Chicago offers live Chicago blues every night of the week. The drinks are inexpensive for a city bar, with classic cocktails Tom Collins or Whiskey Sour just $6.
Tunes With Old School Cool
The Zebra Lounge piano bar is a cozy venue tucked away in the Gold Coast’s Canterbury Courts apartment building. In business since the end of Prohibition, the club is the kind of place you’re likely to hear classics like Frank Sinatra’s “My Kind of Town (Chicago Is).” Color-splashed Hotel Indigo is an ideal home base for club-hopping through the Gold Coast. For a satisfying nightcap, the boutique hotel’s cozy 1224 Bistro and Bar offers a bracing Irish Coffee with whipped cream and a cherry on top, which pairs well with the homemade chocolate chip cookies offered at the front desk. The friendly bartenders will also serve it as hair of the dog, or send it up with room service.
North side Art Deco gem The Green Mill Cocktail Lounge is the granddaddy of Chicago jazz clubs, dating back to 1907. During Prohibition, mob boss Al Capone is said to have commanded a booth that allowed him to keep an eye on both entrances and bootleggers smuggled in liquor through tunnels. You can enjoy a more lawful night by sinking into his favorite booth and soaking in live jazz or swing music. The Sunday night poetry slam has been rolling since 1986, so bring your favorite poem or release your inner heckler with the rest of the crowd. The weekly prize is $10, which host Mark Smith is fond of saying “can feed a poet for a week.”
Open-Air Music to Your Ears
From June to September, the Ravinia Festival in suburban Highland Park offers one of the country’s oldest outdoor music festivals in a jewel of a setting. Stars from John Legend to Diana Krall take bookings at Ravinia for the chance to perform in its pastoral setting. You can either picnic or take advantage of on-site dining from a variety of restaurants. Dog Show restaurant is site-appropriate — you can munch on a Chicago-style steamed hot dog here, washed down with a Goose Island Four Star Pilsner from Amber Grill.
The Frank Gehry-designed Jay Pritzker Music Pavilion hosts a free Millennium Park Summer Music Series mid-June through mid-August. The 4,000-seat Pritzker bandshell offers shows from jazz to funk under stunning architecture, even by Chicago’s standards. Bring a picnic (Chicago-style deep dish pizza, for instance) to the adjoining Great Lawn, and with overhead speakers you’ll be surrounded by music under summer skies.
So whether you’re looking for smoking hot blues or outdoor jazz on a summer night, Chicago music has you covered for all seasons.