The third region of the Tune Tournament is dedicated to the Windy City. Chicago has continued to maintain its reputation as a major hub for hip hop artists, with Chance the Rapper, Vic Mensa, and Joey Purp on the field this year among a host of others. Do they have what it takes to topple Chicago veterans such as Wilco, Jim O’Rourke or Andrew Bird? Only time will tell.

I’m a big fan of secret shows (I mean, who isn’t?), and earlier this year Chance the Rapper, arguably the biggest name in Chicago hip hop right now, played a last-minute gig at iconic venue The Metro. Just a block away from Wrigley Field in Lakeview, the show sold out almost instantly, selling tickets exclusively through the venue’s box office. Props to The Metro for nixing the online option, negating those pesky online transaction fees and cyber scalpers!

Who moves on to the round of 32? Cast your votes and spread the word, as these eight matchups close on Friday, November 25 at noon.

Matchup 1: Wilco – “If I Ever Was a Child” vs. Edamame – “Tree Shadows”

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Matchup 2: Jim O’Rourke – “Half Life Crisis” vs. Jeremih – “Oui”

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Matchup 3: Donnie Trumpet – “Windows” vs. Twin Peaks – “Walk to the One You Love”

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Matchup 4: Whitney – “Golden Days” vs. Veruca Salt – “Laughing in the Sugar Bowl”

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Matchup 5: Andrew Bird – “Truth Lies Low” vs. Owen – “Lost”

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Matchup 6: Vic Mensa – “Down on My Luck” vs. Tortoise – “Hot Coffee”

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Matchup 7: Joey Purp – “Photobooth” vs. DJ Rashad – “Roll Up That Loud”

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Matchup 8: Chance the Rapper – “All We Got” vs. VARSITY – “Amanda”

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You can still participate in the first round matchups for San Francisco and London, and coming Thursday, November 24: First Round Matchups in the Minneapolis Region!