Chicago’s summer energy peaks this weekend with a stellar mix of concerts, comedy, and theater. Whether you’re catching headliners at iconic venues or discovering emerging talent in intimate clubs, there’s something for every mood and taste.
Tip: code GTIX20 takes 20% off ticket prices on every event below — no minimum and no expiry.
- Usher & Chris Brown at Soldier Field
- Kacey Musgraves at United Center
- Jill Scott at The Chicago Theatre
- Esperanza Spalding at City Winery
- Galantis & TELYKAST at The Salt Shed Outdoors
- Second City Mainstage 114th Revue
- Therapy Gecko at Heath Mainstage
- SAW The Musical at Heath Mainstage
- Ballet of Lights: Sleeping Beauty at Athenaeum Center
- Eagles of Death Metal at Metro Chicago
Usher & Chris Brown at Soldier Field
Fri, Aug 21, 7:00 PM · Soldier Field · from $105
Two R&B titans share the stage at Chicago’s largest venue for a night of hits spanning decades. Expect smooth vocals, sharp choreography, and the kind of energy that only comes from pairing two of the genre’s biggest names.
Kacey Musgraves at United Center
Fri, Aug 21, 7:30 PM · United Center · from $21
The Grammy-winning country-pop artist brings her sophisticated sound and visual spectacle to one of Chicago’s premier arenas. Her blend of country roots and pop sensibility makes for a show that appeals far beyond genre purists.
Jill Scott at The Chicago Theatre
Sat, Aug 22, 7:30 PM · The Chicago Theatre · from $286
The neo-soul legend performs in one of the city’s most beautiful historic venues, delivering the kind of intimate-yet-grand experience that defines The Chicago Theatre. Her rich voice and catalog of classics guarantee an unforgettable evening.
Esperanza Spalding at City Winery
Fri, Aug 21, 7:30 PM · City Winery – Chicago · from $260
The virtuoso bassist and vocalist brings her genre-defying jazz and world music fusion to an elegant wine venue. Her technical brilliance and warm presence create an immersive, conversation-worthy performance.
Galantis & TELYKAST at The Salt Shed Outdoors
Sat, Aug 22, 6:30 PM · The Salt Shed Outdoors – Chicago · from $120
Swedish electronic duo Galantis takes over the outdoor venue with infectious dance-pop and electronic production. Perfect for a summer night under the stars with high-energy beats and euphoric melodies.
Second City Mainstage 114th Revue
Fri, Aug 21, 6:30 PM · Mainstage at Second City – Chicago · from $107
Chicago’s legendary comedy institution delivers its latest sketch and improv show, featuring the sharp wit and topical humor Second City is known for. A perfect introduction to the talent pipeline that’s launched countless comedy careers.
Therapy Gecko at Heath Mainstage
Fri, Aug 21, 7:15 PM · Heath Mainstage At The Den Theatre · from $70
The rising comedy star brings absurdist humor and infectious energy to The Den Theatre. Known for surreal storytelling and crowd interaction, Therapy Gecko delivers laughs that linger long after the show ends.
SAW The Musical at Heath Mainstage
Sat, Aug 22, 5:00 PM · Heath Mainstage At The Den Theatre · from $135
The horror-thriller franchise gets the musical treatment with dark humor and theatrical spectacle. This unexpected adaptation brings a fresh twist to a beloved franchise with live music and stagecraft.
Ballet of Lights: Sleeping Beauty at Athenaeum Center
Sat, Aug 22, 4:00 PM · Historic Main Stage at Athenaeum Center – IL · from $95
A sparkling reimagining of the classic ballet with elaborate lighting design and contemporary choreography. This production transforms a familiar story into a visually stunning experience that appeals to both ballet enthusiasts and newcomers.
Eagles of Death Metal at Metro Chicago
Fri, Aug 21, 8:00 PM · Metro Chicago · from $54
The hard rock outfit brings raw energy and guitar-driven anthems to the iconic Metro venue. A no-frills rock show perfect for fans who want loud, unapologetic rock and roll in an intimate setting.
With everything from arena-sized R&B spectacles to intimate jazz sets and comedy clubs, this weekend offers something for every taste. Book early—the big shows fill fast.
