1) DAVE MATTHEWS BAND CARAVAN | July 8–10 | Lakeside
Stellar supporting lineup (Emmylou Harris, Sharon Jones, the Flaming Lips) plus nightly sets by DMB mark the first concert at the scenic former site of U.S. Steel South Works. $195 for three-day pass. 800-594-8499, dmbcaravan.com

2) TV ON THE RADIO AND CUT COPY | July 17 | Pitchfork
The indie rock gathering comes to a funky finish with TV on the Radio’s heady mix of electronic art-rock and soul. Stake your spot early and catch Cut Copy, an Aussie dance-pop group banging out slinky grooves and confectionary melodies. $45 per day. pitchforkmusicfestival.com

3) THE 5 BROWNS PERFORM NICO MUHLY | August 9 | Ravinia
Five pianos, 440 keys. Siblings Ryan, Melody, Gregory, Deondra, and Desirae—all Juilliard grads—perform a world premiere by contemporary classical “It” guy Nico Muhly. $10–$50. ravinia.org

4) JERRY LEE LEWIS | July 9 | Congress Theater
Now 75 years old and as ornery as ever, the Killer gives his first Chicago performance in 13 years on the heels of a live record produced by Jack White. From $25. 773-276-1235, ticketfly.com

5) IRON AND WINE | June 6 | Millennium Park
Acclaimed songwriter Sam Beam weaves intricate stories with the threads of emotional harmonies in a rare outdoor appearance. FREE. millenniumpark.org

6) FLORENCE AND THE MACHINE | June 18 | Aragon
The 2011 Grammy-nominated singer brings her unmatched lungs for a long-awaited return. Sold out.

7) YEMEN BLUES AND ETRAN FINATAWA | July 21 | Millennium Park
A dazzling double bill of bands from Israel and Niger. Each combines the soaring sound of chant with the blues, plus jazz horns and tribal drumming, respectively. FREE.

8) ITZHAK PERLMAN AND LEON FLEISHER | August 6 | Ravinia
These two lions have played together before, but this time Perlman steps behind the podium to conduct the piano savant. Such a treat would cost you dearly at Symphony Hall. Here, reserved seats are $25—and the lawn is FREE.

9) OTIS CLAY | August 4 | Millennium Park
Backed by horns, the great Chicago soul and gospel singer pays tribute to towering legends Mahalia Jackson and Sam Cooke. FREE.

10) GRACE POTTER & THE NOCTURNALS | June 3 | House of Blues
The standout of 2010’s Chicago Bluegrass and Blues Fest finally nabs a headlining spot, the perfect opportunity to shed those Tina Turner comparisons. $25–$30. 866-448-7849, houseofblues.com/chicago

11) SADE AND JOHN LEGEND | August 5–7 | United Center
The global Soldier of Love proves some things are worth the wait as she returns to touring after ten years for a residency with John Legend. From $49.50. 800-745-3000, unitedcenter.com

12) BLONDE REDHEAD | July 18 | Millennium Park
The only thing more haunting than Blonde Redhead’s 15-year collection of psychedelic dreamscapes is listening to it under the stars. FREE.

13) CHICAGO BLUES: A LIVING HISTORY | July 1 | Buddy Guy’s Legends
Five staples of the blues scene—harmonica players Billy Boy Arnold and Billy Branch with guitarists Lurrie Bell, Carlos Johnson, and John Primer—come together in a thrilling celebration of a new CD. $20. 312-427-1190, buddyguys.com

14) ROBERT PLANT | June 16 | Ravinia
The rocker is arguably only the third-best singer in his group Band of Joy, which includes the vocalist Patty Griffin and singer-guitarist Buddy Miller. Expect rootsy renditions of Plant’s recent folk-rock material and Led Zeppelin classics. From $22.

15) EIGHTH BLACKBIRD | August 22 | Millennium Park
In February, this local sextet’s performance of Steve Reich’s masterpiece Music for 18 Musicians sold out the MCA. Now it’s back—with Reich’s Pulitzer-winning Double Sextet (a piece he wrote for them) added to the bill. FREE.

Photography: (Florence of Florence and the Machine) Mark Allan/AP; (Fleisher) courtesy of Ravinia Festival; (Kazu Makino of Blonde Redhead) Pier Nicola D’Amico