Must-See Chicago Concerts and Comedy Shows in May
May features a massive amount of must-see shows in Chicago. From stadium concerts to punk rock parties, here’s a list of some of the amazing artists bringing their talents to the Windy City this month.
Chaka Khan, Patti LaBelle, Gladys Knight, and Stephanie Mills – United Center May 30
Why see only one legend when you can see four? Chaka Khan, Patti LaBelle, Gladys Knight, and Stephanie Mills are joining forces for a sure-to-be unforgettable night of music. Billed as The Queens! 4 Legends – 1 Stage, this powerhouse performance is taking place at the United Center on May 30.
Rhiannon Giddens & The Old-Time Revue – Thalia Hall May 9
Grammy Award-winning singer, songwriter and multi-instrumentalist, Rhiannon Giddens – who also happens to be a MacArthur Genius grant recipient and Pulitzer Prize winner – is set to take the stage at Thalia Hall on May 9. Her 2023 album, You’re the One, beautifully blends Blues, Jazz, Cajun, Country, Rock, and Gospel, so fans of all aspects of American music are in for a treat.
Amyl and the Sniffers – The Salt Shed May 8

Fresh off their frenzied set at Coachella, Australian punks Amyl and the Sniffers are bringing their high-energy songs to The Salt Shed on May 8. Circle pits and crowd surfers will be part of the programing. It’s probably a good idea to start training now so you’ll be ready to rock just as hard as Amy, Bryce, Declan, and Gus when the time comes.
Nikki Glaser – The Chicago Theatre May 22
She cracked us all up at The Golden Globe Awards and now comedian Nikki Glaser is set to headline a pair of shows at The Chicago Theatre on May 22. Glaser is known for her blend of sharp wit and provocative humor – the perfect combination for a night full of laughter.
Valerie June – Park West May 28

Rebellious Magazine favorite Valerie June will be entertaining and uplifting fans during her Park West performance on May 28. Her latest album, Owls, Omens, and Oracles – which just dropped on April 11 – marks a return to the singer-songwriter’s indie roots while still featuring the innovations for which she is known.

Also this month, Yola is bringing her Sovereign Soul Tour to Thalia Hall on May 25 and Tennis – who recently released what is being billed as their final album – will be performing at The Salt Shed on May 23. Paula Poundstone is set to take the stage at The Den on May 17 and Yaz’s Allison Moyet has a show at The Vic on May 7. Last, but most certainly not least, Beyoncé (!!!!!!!) is taking over Soldier Field for a trio of shows on May 15, 17, and 18 on the Cowboy Carter Tour.
So far, May is proving to be the month to beat in terms of incredible entertainment.