The Haute Seeker

11 Chicago Fall Festivals to Look Forward to

Chicago’s summer festivals are undoubtedly amazing experiences, but there’s more to enjoy beyond that season. In fact, the fall season also boasts a variety of festivals that you can look forward to.

Some of my favorite festivals take place in the fall, here are ones that you shouldn’t miss this year.

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Fall Festivals in Chicago

1. WingOut Chicago

WingOut Fall Festivals Chicago The Haute Seeker
Vendor Cooking Wings // Image via WingOut Chicago

Whether you prefer Classic Buffalo or Habanero, you can indulge in your favorite wing flavor at WingOut Chicago located at Gallagher Way. This fall festival caters to wing lovers and showcases wings from the top bars and restaurants in the Chicagoland area from September 2nd – 3rd.

Admission: $20 – $149

2. Taste of Polina

Taste of Polina Promotional Video // Via Youtube

Experience the largest Polish festival in the United States without leaving the city of Chicago. The Taste of Polina takes place September 2nd – 5th offering non-stop live music, food, entertainment, and fun for four days. The popular family-friendly event is a one-of-a-kind food festival in Chicago and includes plenty of activities for kids of all ages to enjoy, including tasting and cooking classes, carnival rides, a casino, a climbing wall, and more. Experience a true cultural experience with authentic Polish food, exhibitions, and more in Chicago.

Haute Tip: Park and ride for free. Shuttle services are available all weekend from the Irish American Heritage Center.

Admission: $15, Kids 12 and under are FREE.

3. African Festival of the Arts

Vendors at The African Festival of the Arts // Image via Facebook

Experience culture from various African Diasporas at the African Festival of the Arts. The annual Labor Day weekend festival takes over Chicago’s Washington Park from September 1st through the 4th as a simulated African village. Attendees are transported across the Diaspora with interactive engagements, vibrant drumming, museum quality and collectible artifacts, colorful and rich handwoven fabric and textile, and other program spaces and Interactive spaces.

Admission: $0 – $375

4. Taste of Chicago

Guests at the Taste of Chicago // Image via DCASE

Returning to its Grant Park home near Buckingham Fountain for 2023, Taste of Chicago will once again showcase the vibrant diversity of the City of Chicago’s culinary offerings alongside world-class musical performances, drawing visitors from across the country and around the globe. This fall festival takes places Friday, September 8 – Sunday 10 from 11 a.m. to 9 p.m.

Admission: Free Entry

5. World Dumpling Fest

World Dumpling Fall Festivals Chicago The Haute Seeker
Vendors at the World Dumpling Fest // Image Chicago Cultural Alliance

Get ready to immerse yourself in a cultural extravaganza in Chicago, where music, dance, and a delectable variety of dumplings from 15 different cultures await you. The World Dumpling Fest brings vibrant and diverse communities together on September 9th and 10th in Logan Square.

Admission: $25 – $50 includes a sampler pack of tickets. Each ticket can be redeemed from a vendor for one serving of dumplings.

6. Hyde Park Jazz Festival

Enjoy world-renowned jazz artists for free at the annual Hyde Park Jazz Festival. The Hyde Park Jazz Festival is a collaborative platform dedicated to supporting the presentation and ongoing development of jazz, particularly on the South Side of Chicago. Watch your favorite performers and discover new artists from September 23rd through the 24th.

Admission: Entry is Free; $10 Donation Appreciated

7. Chicago Gourmet

Chicago Gourmet Fall Festivals Chicago The Haute Seeker
Attendees at Chicago Gourmet // Image via Illinois Restaurant Association

Chicago Gourmet is one of the most highly anticipated culinary events of the year. This year’s lineup features travel-inspired culinary experiences, a world-class roster of featured chefs, and more. Great adventure and fantastic food await at this year’s festival. Experience the culinary journey from September 21st through 24th in Grant Park.

Admission: $70 – $1,999

What Else We’re Reading

8. Oktoberfest Chicago

Guests at Oktoberfest Chicago Fall Festival The Haute Seeker
Guests at Oktoberfest Chicago // Image via St. Alphonsus Facebook Page

Bring on autumn and pull out the lederhosen! One of Chicago’s most popular celebrations of fall and all things Bavarian — Oktoberfest Chicago at St. Alphonsus — returns for its 20th year of seasonal revelry from September 22nd – 24th. It takes place both in and outside the iconic church located in Chicago’s West Lakeview neighborhood.

Admission: $10 Entry

9. Apple Fest

Chicago Apple Fest Promotional Video // Via Youtube

Join the Lincoln Square Ravenswood Chamber of Commerce in welcoming fall with their 36th Annual Apple Fest. The event will be held on Saturday, September 30th, and Sunday, October 1st from 9 a.m. to 6 p.m. The Apple Fest is a beloved tradition in Lincoln Square, where locals come together to indulge in apple delights and the start of the fall season.

Admission: $5 Suggested Donation

10. Lincoln Park Wine Fest

Attendees at the Lincoln Park Wine Fest // Image Wrightwood Neighbors Associate

Sample wines from around the world during this cool(literally) fall festival October 6th – 8th. The Lincoln Park Wine Fest transforms tranquil Jonquil Park into an open-air market featuring wine and food pavilions.

Admission: $35 – $98

11. Open House Chicago

Penthouse at Hyde Park, photo by Anna Munzesheimer⁠ Fall Festivals The Haute Seeker

Ever wonder what was behind the doors of some of Chicago’s most iconic architectural landmarks? Get a peek inside with Open House Chicago. A personal favorite fall festival, the Chicago Architecture Center hosts a free public festival that offers self-guided history and architecture trails throughout Chicago, talks and programming, and behind-the-scenes access to architecturally, historically, and culturally significant sites across the city.

Discover 20 Chicago neighborhoods and 150 sites during this event on October 14th-15th. Explore themes of neighborhood investment, community engagement, and historic preservation.


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