Chicago is a city that never sleeps, and next week is no exception. From thrilling sports matchups and world-class performances to cultural celebrations and hands-on workshops, the Windy City is brimming with activities for every interest. Whether you’re a foodie, a music lover, a sports enthusiast, or someone who simply loves exploring, this week’s lineup has something for you. Here’s a curated guide to the top events happening in Chicago from September 28 to October 4, 2025.
Sunday, September 28: A Day of Culture and Action
- Randolph Street Fest
Kick off your week at this world-famous European-style antique and vintage market. With live music, delicious food, and a wide array of unique vendors, it’s a treasure hunter’s paradise.
Location: Randolph Street Market District - Joffrey Ballet – Carmen
Experience the Joffrey Ballet’s stunning rendition of Carmen at the Lyric Opera of Chicago. This reimagined classic is a must-see for dance and theater enthusiasts.
Location: Lyric Opera of Chicago - Life Time Chicago Half Marathon + 5K
Join thousands of runners in this iconic race through Jackson Park. Whether you’re running or cheering, the energy and excitement are contagious.
Location: Jackson Park - S. Carey, John Raymond, and Shadowlands
Enjoy an intimate evening of music at Schubas Tavern, where indie, jazz, and folk influences come together in a collaborative performance.
Location: Schubas Tavern - West Side Story (1961) Screening
Relive the magic of this classic musical film at the Chicago Public Library. Stick around for a post-screening discussion to dive deeper into its themes.
Location: Chicago Public Library - Ava – The Secret Conversations
Step into the life of Hollywood legend Ava Gardner with this play based on her memoir. Performed at the Studebaker Theater, it’s a compelling journey into the Golden Age of Hollywood.
Location: Studebaker Theater
Monday, September 29: Rock and Soul
- Garbage with Starcrawler
Rock out with alternative legends Garbage as they take the stage with Starcrawler at The Salt Shed. Expect a night of electrifying performances and nostalgic hits.
Location: The Salt Shed - Motown Showdown
Groove to the soulful sounds of Motown at City Winery Chicago. This themed music performance is sure to get you dancing in your seat.
Location: City Winery Chicago
Tuesday, September 30: Bourbon and Beyond
- 11th Annual Bourbon Fest
Celebrate Bourbon Heritage Month in style at the Untitled Supper Club. Sip on a curated selection of bourbons while enjoying a sophisticated evening of tastings and camaraderie.
Location: Untitled Supper Club
Thursday, October 2: Art and Athletics
- Halo-Halo Project
Immerse yourself in Filipino American culture at this art exhibition and event. Hosted at the Harold Washington Library Center, it’s a celebration of heritage and creativity.
Location: Harold Washington Library Center - Loyola Chicago Ramblers Women’s Soccer
Cheer on the Loyola Ramblers as they face off against the George Washington Revolutionaries. A thrilling match awaits soccer fans!
Location: Loyola Soccer Field
Friday, October 3: Sports and Sounds
- NLDS: TBD at Chicago Cubs
Baseball fans, rejoice! The Chicago Cubs kick off their National League Division Series at Wrigley Field. Don’t miss the chance to witness playoff action in one of baseball’s most iconic stadiums.
Location: Wrigley Field - Chicago Blackhawks vs. St. Louis Blues
Hockey season is back! Watch the Blackhawks take on the Blues in what promises to be an intense rivalry game.
Location: United Center - Pool Kids with Truth Club and Pony
Catch an unforgettable live music performance at Lincoln Hall. With a lineup featuring Pool Kids, Truth Club, and Pony, it’s a night of indie rock bliss.
Location: Lincoln Hall
Saturday, October 4: Creativity and Community
- WONDER Tap Dance Performance
Experience tap dance like never before with Caleb Lawrence Jackson’s innovative performance at the Harold Washington Cultural Center. This show redefines tap as a musical art form.
Location: Harold Washington Cultural Center - Vejigante Mask Collage Workshop
Get crafty at the Lincoln Belmont Branch of the Chicago Public Library. Create your own Puerto Rican Carnival mask in this family-friendly workshop.
Location: Lincoln Belmont Branch Library - WCPW®: Home!
Bring the whole family to this professional wrestling event at Inner City Impact. Expect high-energy matches and plenty of entertainment for all ages.
Location: Inner City Impact
Summary: A Week to Remember
From the vibrant Randolph Street Fest to the thrilling Chicago Cubs playoff game, next week in Chicago is packed with unforgettable experiences. Whether you’re exploring cultural events like the Halo-Halo Project, enjoying live music from Garbage or Pool Kids, or cheering on your favorite sports teams, there’s no shortage of excitement. So grab your calendar, plan your week, and get ready to make the most of everything Chicago has to offer!
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