Chicago’s biggest weekend of summer kicks off with Lollapalooza at Grant Park—a three-day festival that spills into the city’s clubs and venues with official aftershows. Beyond the festival grounds, you’ll find Broadway musicals, stand-up comedy, blues, R&B, and electronic music scattered across iconic Chicago rooms.
- Lollapalooza 2-Day Pass (Fri & Sun)
- & Juliet at the Auditorium Theatre
- bbno$ Official Lollapalooza Aftershow
- Clipse Lollapalooza Aftershow
- Grant Park Orchestra: Gershwin’s An American in Paris
- SAW The Musical at The Den Theatre
- Khamari at Park West
- Selwyn Birchwood at Buddy Guy’s Legends
- Chicago’s Best Stand Up at The Laugh Factory
- Spacey Jane at Vic Theatre
Lollapalooza 2-Day Pass (Fri & Sun)
Fri, Jul 31, 3:30 AM · Hutchinson Field Grant Park · from $1233
Chicago’s flagship music festival takes over Hutchinson Field in Grant Park with hundreds of artists across multiple stages. A two-day pass lets you dip in and out across Friday and Sunday, catching everything from headliners to emerging acts across rock, pop, hip-hop, and electronic.
& Juliet at the Auditorium Theatre
Fri, Jul 31, 7:30 PM · Auditorium Theatre – IL · from $105
This joyful musical reimagines Shakespeare’s “Romeo and Juliet” from Juliet’s perspective, with a modern pop-infused score and infectious energy. It’s a perfect counterweight to the festival chaos—a night of theatre magic in one of Chicago’s most storied venues.
bbno$ Official Lollapalooza Aftershow
Fri, Jul 31, 10:00 PM · House Of Blues – Chicago · from $41
The Canadian rapper and producer brings his playful, high-energy set to House of Blues on Friday night. If you’re catching Lolla during the day, this is an ideal way to keep the momentum going without leaving the city.
Clipse Lollapalooza Aftershow
Fri, Jul 31, 11:00 PM · Riviera Theatre – IL · from $73
The legendary Virginia hip-hop duo reunites for a rare performance at Riviera Theatre on Friday. Expect classic tracks and the chemistry that made them icons of early-2000s rap.
Grant Park Orchestra: Gershwin’s An American in Paris
Fri, Jul 31, 6:30 PM · Harris Theater · from $108
Friday evening, catch the Grant Park Orchestra performing Gershwin’s jazzy, romantic masterpiece at Harris Theater. It’s a sophisticated, accessible entry point to classical music with one of Chicago’s finest ensembles.
SAW The Musical at The Den Theatre
Sat, Aug 1, 5:00 PM · Heath Mainstage At The Den Theatre · from $135
Saturday brings this theatrical adaptation of the cult horror franchise to Heath Mainstage. Dark, visceral, and theatrically inventive, it’s for fans of horror and bold stage design.
Khamari at Park West
Fri, Jul 31, 11:00 PM · Park West · from $59
The rising R&B artist brings smooth vocals and contemporary soul to Park West on Friday night. A more intimate alternative to the festival, perfect for fans of modern R&B.
Selwyn Birchwood at Buddy Guy’s Legends
Fri, Jul 31, 8:00 PM · Buddy Guys Legends · from $51
Friday night, catch this blues guitarist and vocalist at Chicago’s most iconic blues club. Birchwood’s soulful playing and warm stage presence make for an authentic Chicago blues experience.
Chicago’s Best Stand Up at The Laugh Factory
Fri, Jul 31, 9:15 PM · The Laugh Factory – Chicago · from $75
Friday night comedy showcase featuring local and touring comedians. A fun, low-pressure way to laugh between music sets without committing to a full festival day.
Spacey Jane at Vic Theatre
Fri, Jul 31, 11:00 PM · Vic Theatre · from $66
The Australian indie-rock band plays Vic Theatre on Friday night with infectious melodies and tight arrangements. A great mid-size venue show for fans of contemporary alternative rock.
Book early for Lollapalooza and popular aftershows—many sell out. Check venue websites for door times and any age restrictions on smaller shows.
