Introduction
Chicago is a city that never sleeps, and this week is no exception! From September 22 to 28, 2025, the Windy City is packed with exciting events, festivals, live music, cultural experiences, and sports. Whether you’re a foodie, a music lover, an art enthusiast, or a sports fan, there’s something for everyone to enjoy. Here’s your ultimate guide to the top things to do in Chicago this week.
Festivals and Special Events
1. Chicago Gourmet
Indulge in a food lover’s paradise at Chicago Gourmet, the city’s premier culinary festival. This multi-day event features food tastings, cooking demonstrations, and exclusive dinners hosted by renowned chefs. Whether you’re a foodie or just looking to treat your taste buds, this festival is a must-attend.
- When: September 25–28
- Where: Various locations
2. Musika SamaSama Filipino Festival
Celebrate Filipino culture at this free, family-friendly festival. Enjoy delicious Filipino food, shop for crafts, and groove to live music from the SamaSama Project. It’s a vibrant celebration of community and heritage.
- When: Saturday, September 27
- Where: Eugene Field Park
3. Hubbard Haus Oktoberfest Street Festival
Raise a stein and toast to Oktoberfest in River North! This lively street festival features authentic German food, drinks, and live bands, bringing a slice of Bavaria to Chicago.
- When: Saturday, September 27
- Where: Hubbard Street
4. Randolph Street Market Festival
Step into a European-style antique and vintage market in the heart of the West Loop. Browse unique finds, enjoy live music, and savor delicious food at this beloved market festival.
- When: September 27–28
- Where: West Loop
5. Imagine, Create, Activate!
Dive into an immersive experience exploring the transformative power of arts and culture. This event features curated programs, networking opportunities, and hands-on activities designed to inspire creativity and community engagement.
- When: September 22–24
- Where: Harris Theater for Music and Dance
Music and Nightlife
6. Nourished By Time
Kick off your week with a live performance by the artist Nourished By Time at Lincoln Hall. Expect an intimate evening of soulful music and captivating vibes.
- When: Monday, September 22
- Where: Lincoln Hall
7. Deltron 3030
Catch the legendary hip-hop group Deltron 3030 at the House of Blues. Known for their futuristic beats and thought-provoking lyrics, this is a show you won’t want to miss.
- When: Tuesday, September 23
- Where: House of Blues Chicago
8. The Blessed Madonna
Dance the night away to the electronic beats of The Blessed Madonna at Smart Bar. This is the perfect way to let loose and enjoy Chicago’s vibrant nightlife.
- When: Saturday, September 27
- Where: Metro / Smart Bar
9. Lil Tracy with Cold Mountain
End your Saturday with a high-energy performance by Lil Tracy and Cold Mountain at the House of Blues. Their unique sound and dynamic stage presence promise an unforgettable night.
- When: Saturday, September 27
- Where: House of Blues Chicago
Arts and Culture
10. Ghost Fetus
Experience the darkly comedic play Ghost Fetus, presented by Trap Door Theatre. This intriguing story of a ghost seeking revenge is sure to leave you thinking long after the curtain falls.
- When: September 25–27
- Where: Trap Door Theatre
11. Carmen (Joffrey Ballet)
Witness the U.S. premiere of Liam Scarlett’s reimagining of Carmen, performed by the Joffrey Ballet. This stunning production combines the timeless music of Georges Bizet with breathtaking choreography.
- When: September 25–28
- Where: Lyric Opera of Chicago
12. Tom & Eliza
Reflect on life’s choices with Tom & Eliza, a thought-provoking play by TUTA Theatre. This production offers a unique perspective on the ever-spinning world we live in.
- When: September 25–28
- Where: TUTA Theatre Chicago
13. Messages & Mediums: Decorative Arts from South Asia
Explore the rich decorative arts of South Asia in this new exhibition at the South Asia Institute. From intricate designs to cultural themes, this exhibit is a feast for the eyes and the mind.
- When: Opening Thursday, September 25
- Where: South Asia Institute (SAI)
Sports
14. Chicago Bears vs. Dallas Cowboys
Cheer on the Chicago Bears as they take on the Dallas Cowboys in an exciting Monday night NFL game at Soldier Field. The energy of the crowd is sure to be electric!
- When: Monday, September 22
- Where: Soldier Field
15. Bloomingdale Trail 5K
Lace up your running shoes for the Bloomingdale Trail 5K. This timed race offers a scenic route along the trail, with shorter dashes available for kids.
- When: Saturday, September 27
16. Tough Cup XI
Watch rowers of all classes compete in a thrilling 6k race on Chicago’s waterways. The Tough Cup XI is a unique sporting event that showcases the city’s love for water sports.
- When: Saturday, September 27
Summary
This week in Chicago is packed with unforgettable experiences, from culinary delights and cultural celebrations to live music, theater, and sports. Whether you’re exploring the Randolph Street Market, dancing to The Blessed Madonna, or cheering on the Chicago Bears, there’s no shortage of excitement. Make the most of your week by diving into these incredible events and creating memories in the Windy City!
Want more events? Check out: https://www.enjoyillinois.com/things-to-do/festivals-and-events/
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