by Grind and Unwind | Published October 1, 2025
Chicago in October isn’t just about football season and pumpkin patches—it’s about the city heating up with some of the biggest names in rap and R&B. Whether you’re looking to turn up or vibe out Grind & Unwind has you covered.
We’re breaking down 7 artists hitting Chicago this October, in order of when they’re blessing the stage. Grab your people, clear your calendar, and let’s get into it.
1. Rio Da Yung OG — October 11 @ PATIO THEATRE (CLICK FOR TICKETS)
Rio might be the most unique artist rapping, period. Straight out of Flint, Michigan, Rio brings that gritty, gutta sound that fans can’t get enough of. He’s one of those artists that does what he wants and that freedom is enough to build a strong fanbase. His raw storytelling and funny delivery will set the tone for Chicago’s October concert run. If you like unfiltered energy and unapologetic bars, this is your night.
2. Doechii — October 14 @ BYLINE ARAGON BALLROOM (CLICK FOR TICKETS)
TDE’s rising star, Doechii, is bringing her unique blend of rap, R&B, and futuristic vibes to Chicago. She’s fearless on stage, mixing playful melodies with lyrical bite. Expect a show that’s as bold as her music—colorful, high-energy, and unforgettable.
3. J.I.D — October 18 @ BYLINE ARAGON BALLROOM (CLICK FOR TICKETS)
Known for his rapid-fire flows and thought-provoking lyricism, J.I.D is one of Dreamville’s brightest stars. When he touches the mic, it’s all about precision and passion. Chicago fans know this show is going to be an instant classic—don’t sleep on it.
4. Giveon — October 20 @ BYLINE ARAGON BALLROOM (CLICK FOR TICKETS)
Time to switch gears into the smooth zone. Giveon’s deep, soulful voice has made him one of R&B’s most captivating artists. His Chicago stop will be the perfect night for couples, late-night vibes, and anyone who wants to let the music just hit different.
5. Joey Bada$$ — October 23 @ THE RIVERIA THEATRE (CLICK FOR TICKETS)
Brooklyn meets Chicago for one night only. Joey Bada$$ brings that nostalgic 90s hip-hop essence with a modern twist. His lyrical depth and conscious energy make his shows both a vibe and a movement. Expect bars, energy, and pure artistry.
6. Freddie Gibbs — October 24 @ BYLINE ARAGONE BALLROOM (CLICK FOR TICKETS)
Indiana’s own Freddie Gibbs always treats Chicago like home—and the energy proves it. Known for his sharp storytelling and flawless collaborations, Gibbs brings a show that’s raw, real, and straight-up fire. Fans know: you’re guaranteed a classic night.
7. G Herbo — October 26 @ WINTRUST ARENA (CLICK FOR TICKETS)
We’re closing out the month with none other than Chicago’s own G Herbo. Nobody captures the grind of the city like Herb. When he steps on stage here at home, it’s not just a concert—it’s a celebration of Chicago culture. Expect the city to show out heavy for this one.
🎶 Final Word
October is stacked, and Chicago is the place to be if you live for rap and R&B. From Rio Da Yung OG to Giveon’s slow vibes, the city is serving nonstop reasons to step out and unwind.
👉 Don’t just hear about it—be there. Grab your tickets, mark your calendar, and let Grind and Unwind guide you to the moments you’ll never forget.