Chicago’s summer heat is in full swing, and the city’s venues are packed with live music, comedy, and theatre. Whether you’re catching a major headliner, exploring the underground scene, or settling in for a Broadway-style show, this weekend offers the perfect escape.
- Jack Johnson at Huntington Bank Pavilion
- John Mulaney at Wrigley Field
- Suffs at CIBC Theatre
- Windy City Smokeout Festival
- Ella Mai at The Salt Shed Outdoors
- Paul Oakenfold & The Crystal Method
- SAW The Musical at The Den Theatre
- Chosen Few DJs Picnic and Music Festival
- Grant Park Orchestra: Tchaikovsky Symphony No. 5
- Native Gardens at The Den Theatre
Jack Johnson at Huntington Bank Pavilion
Sat, Jul 11, 7:30 PM · Huntington Bank Pavilion at Northerly Island · from $14
The laid-back singer-songwriter brings his breezy, feel-good sound to the waterfront. Expect acoustic guitars, island vibes, and a crowd ready to unwind as the sun sets over Lake Michigan.
John Mulaney at Wrigley Field
Sat, Jul 11, 8:00 PM · Wrigley Field · from $47
One of comedy’s biggest names takes over the iconic ballpark for an unforgettable night of stand-up. His sharp, observational humor and storytelling prowess make this a can’t-miss comedy event.
Suffs at CIBC Theatre
Fri, Jul 10, 7:00 PM · CIBC Theatre · from $70
This Tony-nominated musical about the women behind the suffrage movement combines witty lyrics with powerful performances. A smart, energetic show that celebrates history and feminism with style.
Windy City Smokeout Festival
Fri, Jul 10, 2:00 PM · Windy City Smokeout · from $62
Lainey Wilson headlines this outdoor country and BBQ fest, bringing twangy vocals and high energy. Perfect for a Friday afternoon of food, drink, and live music in the summer sun.
Ella Mai at The Salt Shed Outdoors
Fri, Jul 10, 7:00 PM · The Salt Shed Outdoors – Chicago · from $65
The R&B and soul singer delivers smooth, soulful vocals in an intimate outdoor setting. Her blend of contemporary R&B and emotional depth makes for an evening of pure musical bliss.
Paul Oakenfold & The Crystal Method
Sat, Jul 11, 8:00 PM · Park West · from $149
Two electronic music legends join forces for a high-energy night of trance and electronic beats. Expect hypnotic rhythms and a packed dance floor at Park West.
SAW The Musical at The Den Theatre
Sat, Jul 11, 5:00 PM · Heath Mainstage At The Den Theatre · from $253
This theatrical adaptation of the horror franchise brings shock, suspense, and dark humor to the stage. A visceral, immersive experience for fans of horror and unconventional theatre.
Chosen Few DJs Picnic and Music Festival
Sat, Jul 11, 7:00 AM · Jackson Park – Chicago · from $129
Chicago’s legendary house music collective hosts an all-day festival in Jackson Park featuring Wayne Williams, Jesse Saunders, and other local icons. A celebration of the city’s deep house music roots.
Grant Park Orchestra: Tchaikovsky Symphony No. 5
Sat, Jul 11, 8:00 PM · Jay Pritzker Pavilion · from $59
Conductor Leonard Slatkin leads the orchestra through one of classical music’s most beloved symphonies at the stunning Jay Pritzker Pavilion. Free admission to this world-class performance under the stars.
Native Gardens at The Den Theatre
Fri, Jul 10, 7:30 PM · The Crosby At The Den Theatre · from $45
A contemporary comedy-drama about neighbors, fences, and cultural divides. Sharp writing and relatable characters make this an engaging evening of theatre that sparks conversation.
Book early—weekend shows fill up fast. Check dates and venues before heading out, and arrive early for outdoor events to snag a good spot.