Chicago is full of excitement this weekend, with events that bring together food lovers, sports enthusiasts, and festival-goers alike. Whether you’re indulging in global dumplings, racing to Wrigley for a good cause, enjoying Oktoberfest festivities, or watching swimmers take on the Chicago River, there’s no shortage of ways to get out and experience the city.
🥟 World Dumpling Festival 2025
📍 Location: Illinois Centennial Monument, 3200 W Logan Blvd, Chicago, IL 60647
📅 Date: Sunday, September 21, 2025
⏰ Event Hours: 12:00 PM – 9:00 PM
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The World Dumpling Festival, hosted by the Chicago Cultural Alliance at the Illinois Centennial Monument in Logan Square, celebrates global dumpling traditions. Attendees can sample dumplings from over 10 neighborhood restaurants—from Latin American empanadas to Polish pierogi and Asian varieties—while enjoying live music, cultural dance performances, and interactive crafts. Admission is free, with food tickets available in advance or on-site. The festival supports the Alliance’s mission to promote and advocate for Chicago’s cultural heritage centers.
🏃♂️ Race to Wrigley 5K Charity Run 2025
📍 Location: 1060 W Addison St, Chicago, IL 60613
📅 Date: Sunday, September 21, 2025
⏰ Event Hours: 8:00 AM – Finish Festival concludes at 10:30 AM
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The 20th Annual Race to Wrigley 5K Charity Run, presented by AbbVie, invites runners and walkers to traverse the Lakeview neighborhood before finishing just steps from the iconic Wrigley Field marquee. Participants have the unique experience of running on the warning track inside the stadium. The event supports Cubs Charities, funding programs that benefit Chicago youth. Registration includes both in-person and virtual 5K options, with discounted rates for children ages 0–10. Spectators are welcome to enjoy the post-race festivities and awards ceremony.
🍺 Oktoberfest with the Cubs 2025
📍 Location: Toyota Camry Lot, 1126 W. Grace St., Chicago, IL 60613
📅 Date: Friday–Sunday, September 19–21, 2025
⏰ Event Hours:
- Friday, September 19: 4:00 PM – 10:00 PM
- Saturday, September 20: 11:00 AM – 10:00 PM
- Sunday, September 21: 12:00 PM – 7:00 PM
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The Chicago Cubs are hosting their inaugural Oktoberfest at Wrigleyville’s Toyota Camry Lot, bringing Bavarian fun to the North Side. This family-friendly event features a ceremonial keg tap, carnival rides, beer tents, German cuisine, live music, and competitions. Attendees are encouraged to wear lederhosen or dirndls. General admission is $15, while VIP tickets ($75) include reserved seating, a free beer, a branded stein, ride tickets, and dedicated restrooms. Guests can also donate nonperishable items to local food pantry Nourishing Hope.
🏊 Chicago River Swim 2025
📍 Location: Chicago Riverwalk, 70 West Wacker Drive, Chicago, IL
📅 Date: Sunday, September 21, 2025
⏰ Event Hours: Athlete Check-In 5:15 AM – Finish Festival Concludes 10:30 AM
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The Chicago River Swim marks the first open-water swim in the Chicago River in nearly a century. Organized by A Long Swim, the event celebrates the river’s environmental revitalization while raising funds for ALS research and youth swim education programs. Swimmers complete a 1–2 mile course from the Dearborn Street Bridge to the Clark Street Bridge. While participation is limited to 500 registered swimmers, the Finish Festival and Awards Ceremony are open to the public, offering a chance for spectators to enjoy the festivities and cheer on the athletes.
No matter what you choose, Chicago offers something fun and memorable for everyone this weekend. Grab your friends or family, explore the city, and make the most of these unique experiences. You never know what new favorite tradition you might discover!
Curious what you missed? Check out last weekend’s events to see all the fun Chicago had to offer!