We did it, Chicago! We made it to outdoor concert and festival season! From an epic weekend of culture and community in Grant Park to a theater performance by one of the best R&B artists in the game, here’s a look at some of the most exciting shows and events happening in the Chicago-area this May.
Ari Lennox – Chicago Theatre – May 16
Rebellious Magazine favorite Ari Lennox is bringing The Vacancy Tour to The Chicago Theatre on May 16. Back in 2023, the R&B superstar transformed the House of Blues into an intimate theatre vibe so we can’t wait to see how she presents her artistic vision at this historic venue.
Demi Lovato – United Center May 1
One of the most highly-anticipated shows of the season is happening on the first of the month as Demi Lovato’s It’s Not That Deep Tour is stopping by the United Center on May 1. This is the pop star’s first major tour in three years and with ADÉLA as a special guest you know it’s going to be a good time.
Rilo Kiley – Chicago Theatre May 29
Rilo Kiley, fronted by the always-great Jenny Lewis, are continuing their reunion run with a headlining show at the Chicago Theatre on May 29. If you missed the band at Riot Fest last year, be sure to pick-up tickets to this performance as this may be your last chance to see the band in Chicago for a long time.
Naomi Watanabe – The Vic Theatre – May 8
If you are looking for lots of laughter, head over to The Vic Theatre on May 8 to see comedian, and fashion leader, Naomi Watanabe. Her viral impersonations and iconic style will delight everyone looking to enjoy an authentic night of entertainment.
Rodrigo y Gabriela – Chicago Theatre – May 13
Rodrigo y Gabriela are celebrating their 20th anniversary with a special tour that is coming to the Chicago Theatre on May 13. Their acoustic guitar stylings have always been unmatched and they have only become more impressive with each passing performance.
Elsewhere this month, Courtney Barnett is headlining the Warm Love Cool Dreams festival which runs May 23-24 and elsewhere on that same weekend, over at Union Park, the brand new Forever Mine Festival will feature performances by Keyshia Cole, Kelly Rowland, Monica, and more. Claire Rosinkranz will be playing Thalia Hall on May 27 while Rayna Greenberg will be taking the stage at The Den on May 1 and May 2. Last but not least, Sueños Music Festival – featuring Kali Uchis, J Balvin, Fuerza Regida, and more – will be taking over Grant Park on May 23 & 24.
There’s nothing like experiencing live music under the stars. See you out there!