Chicago’s entertainment scene is firing on all cylinders this August weekend. Whether you’re catching a world-class orchestra under the stars, diving into a Broadway hit, or dancing to live electronic music, there’s something to match every mood and energy level.
Tip: code GTIX20 takes 20% off ticket prices on every event below — no minimum and no expiry.
- The Outsiders at Cadillac Palace
- Grant Park Orchestra: Beethoven Symphony No. 9
- Tori Amos at Auditorium Theatre
- The Notebook – The Musical
- Three Pianos: Something Corporate, Jacks Mannequin & Andrew McMahon
- Luh Tyler at Avondale Music Hall
- J. Holiday at City Winery
- Alex Edelman at Steppenwolf Theatre
- Zhu at Navy Pier
- SAW The Musical
The Outsiders at Cadillac Palace
Fri, Aug 14, 7:00 PM · Cadillac Palace · from $93
This gripping stage adaptation brings S.E. Hinton’s classic novel to vivid life with dynamic choreography and a stellar ensemble cast. It’s a perfect blend of heart, action, and teenage angst that resonates across generations.
Grant Park Orchestra: Beethoven Symphony No. 9
Fri, Aug 14, 6:30 PM · Jay Pritzker Pavilion · from $91
Conductor Giancarlo Guerrero leads one of classical music’s most transcendent works under the open sky at Jay Pritzker Pavilion. A free or low-cost way to experience world-class orchestral music in one of Chicago’s most iconic outdoor venues.
Tori Amos at Auditorium Theatre
Fri, Aug 14, 8:00 PM · Auditorium Theatre – IL · from $42
The piano-driven alternative icon brings her distinctive voice and intricate arrangements to the historic Auditorium Theatre. Expect an intimate, emotionally charged performance from a true original.
The Notebook – The Musical
Fri, Aug 14, 7:00 PM · Nederlander Theatre at Ford Center for the Performing Arts · from $58
This lush adaptation of the beloved romance captures the sweeping emotion and nostalgia of the story with soaring melodies and beautiful staging. Perfect for a date night or anyone who loves a good cry.
Three Pianos: Something Corporate, Jacks Mannequin & Andrew McMahon
Fri, Aug 14, 7:30 PM · Huntington Bank Pavilion at Northerly Island · from $12
Three piano-driven acts share the stage at Huntington Bank Pavilion for an intimate, stripped-down evening of pop-rock storytelling. Expect emotional singalongs and the kind of connection that only happens when great songwriters play live.
Luh Tyler at Avondale Music Hall
Fri, Aug 14, 7:00 PM · Avondale Music Hall · from $50
Rising hip-hop talent Luh Tyler brings fresh energy and clever wordplay to the stage. A great chance to catch an emerging voice in rap before the crowds get even bigger.
J. Holiday at City Winery
Fri, Aug 14, 7:30 PM · City Winery – Chicago · from $75
The R&B crooner delivers smooth vocals and romantic vibes in an intimate setting. City Winery’s wine-and-music atmosphere makes this the ideal evening for fans of soulful, feel-good performances.
Alex Edelman at Steppenwolf Theatre
Sat, Aug 15, 3:00 PM · Downstairs Theatre At Steppenwolf Theatre – Chicago · from $137
This sharp, energetic comedian brings clever observations and infectious humor to the Downstairs Theatre. Edelman’s high-octane delivery and relatable material make for a memorable comedy night.
Zhu at Navy Pier
Sat, Aug 15, 4:00 PM · Navy Pier – Chicago · from $62
The electronic producer and DJ delivers hypnotic beats and atmospheric soundscapes with Navy Pier’s lakefront backdrop. A perfect late-afternoon or evening escape into electronic music with a view.
SAW The Musical
Sat, Aug 15, 5:00 PM · Heath Mainstage At The Den Theatre · from $65
This theatrical adaptation of the cult horror franchise brings twisted ingenuity and dark humor to the stage. It’s a wild, visceral experience that pushes theatrical boundaries and keeps audiences on edge.
Book early—weekend shows fill up fast in Chicago. Check venue websites for parking, doors, and any special instructions before heading out.
