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101 things to do in Chicago: music and nightlife

Gigantic summer music festivals, killer dance parties, comprehensive record stores and more essential Chicago music and nightlife

Chicago gave the world electric blues, house music, alt-country, Curtis Mayfield and Kanye West. But the music scene here is more than just a history lesson. Our city is the hub of the American music festival. In the summer, there is a major festival every weekend, from the neon beats of Spring Awakening to the closing power chords of Riot Fest. Of course, Lollapalooza is the beast in the heat, taking over Grant Park the first weekend of every August. Heck, we even have music festivals in January. All that action makes for a thriving music culture, with record stores still spread across the city, dance parties in neighborhood bars, and local labels like Drag City, Numero, Bloodshot and Thrill Jockey cranking out collectable LPs. Here are the top things any Chicago music fan must do.

RECOMMENDED: Take a look at all 101 things to do in Chicago

Chicago's best music venues

Gorge on bands and street food at Lollapalooza

Set between Lake Michigan and the Chicago skyline, Lollapalooza is the city's largest music festival, boasting numbers of attendance well in the six digits on a regular day. Large stages, big acts and huge crowds. Taking over all of Grant Park, Lollapalooza is one of the best festivals in the country with a sweet bonus—no camping. Journey to the after-shows, late-night bars, or your hotel room after a long day of sweating and jamming.

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Swing like a gangster with jazz at the Green Mill

Al Capone’s old Uptown haunt is still kicking. A century later, the gangster’s tunnels underneath are used for storage, the hooch is legal and the jazz a little funkier. The late weekend nights are driven by organ combos, going to 5am on Saturday. Piano chanteuse Patricia Barber holds down Mondays, while a former Time Out editor hosts a live talk show of sorts, The Paper Machete, on Friday afternoons.

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See a blues legend in his own blues club

Yes, there is reason to come to Chicago in January. Several of them, actually, but a major one being that living legend Buddy Guy holds down a residency at his eponymous blues joint the first month of every year. See him while you can. The club moved a few years back to a swankier home in the South Loop, once the HotHouse. Even when Buddy isn’t onstage, the 2-bar licks remain tasty, with the cream of the local electric blues crop filling the bills.

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Dance to old school house music at Queen! in Smart Bar

In the ‘80s, house music was invented here in Chicago, in the defunct nightclub known as the Warehouse. While that dance palace might be long gone, many of the pioneering DJs keep on spinning. No better place to catch them than at this Sunday weekly at Smart Bar in Wrigleyville. Derrick Carter leads this party. Jack your body.

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Hoedown with the Hoyle Bros. at Empty Bottle

The Bottle has long been the hub of underground rock in town, and it has the graffiti, stains and smells to prove it. Though the most reliable option on the calendar is this tight and rowdy alt-country combo. The Hoyle Brothers rip up the joint every Friday at 5:30pm. It’s free, leaving you with more cash for cold PBRs. The owners have swanky new venues like Thalia Hall and the Promontory, but this scuzzy bar with the crooked stage is all character.

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Take an old-school selfie in the photo booth at Rainbo Club

This West Town dive bar was the epicenter of Chicago’s indie scene in the ‘90s. Who knows how many make-out sessions and aspiring guitarists were captured in black and white in the photo booth in the back. The album cover of Liz Phair’s seminal Exile in Guyville was snapped in there. Sitting inside feels like a time machine to when Billy Corgan had hair.

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Check out future festival stars at Tomorrow Never Knows

When the calendar turns to January, we Chicagoans need things to look forward to beyond polar vortices. Thankfully, there’s a bevy of reasons to go out in the winter, none better than this annual (indoor!) music festival thrown by Lincoln Hall and Schubas. The focus is on rising acts, and most of the performers are guaranteed to be on larger festival stages come summer. Past headliners like Jessie Ware, Theophilus London, the Orwells and John Newman promptly blew up afterward.

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Get down at the Slo ’Mo dance party

It stands for slow jams for homos, and this monthly shindig continually wins awards for our favorite LGBT jam in town. But it’s for anyone who needs to get down to some Sade (a.k.a. everyone). Get sexy with some D’Angelo and Frank Ocean the third Thursday of every month at Logan Square cocktail bar the Whistler. Killer tunes, fantastic mixed drinks—you’re golden.

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Go crate digging for records at Dusty Groove

Record collectors, if you’re looking for deep, deep rare finds, we have to report that the old shops have long ago been picked over by DJs. Still, those needing funky wax must visit this West Town shop specializing in global rhythms, soul, jazz, funk and soundtracks. Bring a tote bag to the posh and comfortable space, as you’re likely to walk out with several pounds of tropicalia, bop and Kinks reissues.

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Watch some real divas at the Lyric Opera

Opera is centuries old, but credit the Lyric for pushing the artform forward. The company stages the classics with expected grandeur in the beautiful riverside Civic Opera House, but has modernized in recent years with hip new productions, creative consultant Renée Fleming and annual Broadway musicals like Carousel. Okay, so it’s not exactly EDM, but far from fat ladies in horned helmets. Gush over the lavish costumes and sets and have a soprano knock off your socks.

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Take in the Chicago Symphony Orchestra at Symphony Center

Riccardo Muti remains on contract as music director of the CSO until 2020, giving us the greatest living Italian maestro. There are none better at interpreting Verdi, but the wand-tapper also surprised with unexpected juxtapositions in his programs, pairing the classic with the progressive. Composers in residence Anna Clyne and Mason Bates are young and cool, bringing electronic music and Jonny Greenwood into the repertoire.

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Don’t stop believin’ you can sing at a karaoke bar

Chinatown has fun singing parlours like Pop KTV and Sakura, perfect spots to croon off the calories after a round of dim sum. Yet the best karaoke dens in the city remains Alice’s in Avondale, the perfect dive for working through the 50 best karaoke songs ever. Those needing to scratch their “Don’t Stop Believin’” itch downtown should join the delightfully mixed crowd at Brando’s.

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See free gigs in Millennium Park

Shelling out for Lollapalooza, Pitchfork, Ravinia, etc. can quickly burn a hole through your shorts. Thankfully, the city stocks up on killer free concerts in the summer under the sweeping metal of Pritzker Pavilion. Series like Downtown Sound (indie rock), Loops and Variations (electronic meets modern classic) draw cool names, while old standbys like the Grant Park Music Festival and Jazz Fest keep your Loop picnics sophisticated.

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