Must-See Chicago Concerts and Comedy Shows in August
The temperatures are rising and so is the excitement surrounding all of the great events happening in and around Chicago this month. From legendary Lilith Fair performers to late-night Lollapalooza sets, here’s a look at some of the most exciting events happening in the month of August.
Melissa Etheridge & Indigo Girls – Jay Pritzker Pavilion – Aug. 17
Lilith Fair icons the Indigo Girls are joining forces with rock legend Melissa Etheridge for a special night of music right in the heart of Chicago on Aug. 17. Classic songs like “I’m the Only One,” “Come to My Window,” and “Closer to Fine” are expected to be shared throughout the night so be ready to sing-along with a collection of forever favorites.
Jorja Smith – The Salt Shed – Aug. 5

After a scheduled show at the Auditorium Theatre was cancelled earlier this year, Jorja Smith announced that she will be returning to Chicago on Aug. 5 to play The Salt Shed. Fans have been clamoring for a Chicago date from the English singer-songwriter for ages, so the anticipation for this one is sky-high and Smith will most certainly meet the moment with a spectacular show.
Sarah Hester Ross – The Den Theatre – Aug. 22
Cabaret comedian Sarah Hester Ross is bringing her bold feminist humor to The Den Theatre Aug. 22. If you’ve seen her 2024 special Don’t Mess with a Redhead, you already know that you are in for an evening full of bold bits and hilarious comedy that will give your abs a workout from so much laughter.
St. Vincent (with The Lumineers) – Soldier Field – Aug. 30

Technically, this is a Lumineers concert, but we here at Rebellious Magazine believe St. Vincent always deserves top billing. The artist also known as Annie Clark will be providing support for The Lumineers for their Aug. 30 concert at Soldier Field. She’s a tough act to follow, so her impeccable musicianship will surely set the tone for a night of top-tier entertainment.
Cyndi Lauper – Credit Union 1 Amphitheatre – Aug. 5
Parting is such sweet sorrow, but it can also be a joyful occasion to celebrate good memories. Cyndi Lauper is bringing the Girls Just Wanna Have Fun Farewell Tour to Tinley Park on Aug. 5. From the front row to the back of the lawn, every inch of this show will celebrate Lauper’s impressive career as an artist and an activist.

Elsewhere in August, Lollapalooza is still in full swing out in Grant Park and with official aftershows throughout the city including Mary Droppinz at Smoke & Mirrors on Aug. 1 and Remi Wolf at The Salt Shed on Aug. 2. Tate McRae is stopping by the United Center on Aug. 15 and The Beaches are playing The Salt Shed on Aug. 29. Finally, You’re Being Ridiculous: Girl, Bye – a showcase featuring real people telling true stories about their lives – will be at Steppenwolf Aug. 14-16, and features so many Rebellious Magazine favorites like Amy Sumpter, Elizabeth Gomez, and Adrienne Gunn.
Get out there and see as many shows as possible before the summer season comes to an end!