Craig Finn + Esmé Patterson
Old Town School of Folk Music, October 22
As the frontman of the Hold Steady, Craig Finn weaves wordy narrative songs about the transition between youth and young adulthood—a time of life often defined by experimentation, heartbreak and confusion. The subject matter of his latest solo record, Faith in the Future, hews closer to the singer's current circumstances, including many songs written shortly after the death of his mother. With his verbose lyrics and Springsteen-inspired arrangements intact, Finn takes on grief and tragedy with a mantra he coined for his Brooklyn band: "stay positive." ($20, all ages)
Kurt Vile + Waxahatchee
Thalia Hall, October 22 & 23
"I like to be a chameleon and tap into all kinds of different perspectives," Kurt Vile told us in an interview, inadvertently referencing his tendency to write songs centered around heightened versions of his personality. On B'lieve I'm Goin Down, the Philadelphian troubadour casts himself as a world-weary outlaw and an aloof philosopher amid a collection of rollicking folk rock tunes that show off Vile's wit and six-string prowess. Opening act Waxahatchee is similarly existential, grappling with the often directionless state of young adulthood through Katie Crutchfield's leisurely indie rock anthems. (sold out, 17+)
Kendrick Lamar + Future + Meek Mill
United Center, October 25
Even if Kanye decides to perform 808s and Heartbreak at the United Center next month, the WGCI Big Jam will still be the biggest hip-hop bill to hit Chicago this year. Headliner Kendrick Lamar has done very little touring behind his cerebral, lyrically dense LP To Pimp a Butterfly, so the chance to hear cuts like "King Kunta" and "The Blacker the Berry" in person is worth the price of admission. Also on the lineup: Drake collaborator Future, frequently memed emcee Meek Mill, "No Flex Zone" duo Rae Sremmurd and Chicago native Vic Mensa. ($35–$149.50, all ages)