Chicago Food Truck Fest
September 21st – 22nd
LaBagh Woods
25 food trucks will flood this event with free smells and great food. There will also be music, games and sangria to pair with your meal.
Chicago Food Truck Fall Festival
September 21st – 22nd
Saint Paul’s Woods in Morton Grove
promises 40 food trucks, live bands, DJs, beer, wine, and sangria
Glendale Heights Oktoberfest
September 20th – 22nd
Camera Park in Glendale Heights
Head to this suburban German fest complete with food, beer, music and more!
Andersonville Arts Week
September 20th – 22nd
Andersonville
A weekend of events includes an art walk, an art street fest and evening receptions during the Night of 100 Parties on Saturday.
Oaktoberfest
September 20th – 21st
Oak Park
This free fest features live entertainment, music, food, beer and root beer for the kids!
The International Exposition of Contemporary & Modern Art (Expo Chicago)
September 20th – 22nd
Navy Pier
A very cool collection of artists and their work will fill this indoor event. There’s lots to see and even plenty to buy too!
Chicago Japanese Matsuri
September 20th – 22nd
The plaza of NewCity at 1457 N. Halsted Street
This is the event of the weekend for those who LOVE Japanese food. You’ll get an authentic cultural experience complete with drinks, live performances, art and more.
American Craft Exposition
September 20th – 22nd
Chicago Botanic Garden
Walk through the garden and encounter works by more that 140 artists. See the art and chat with their creators too!
Bengtson’s Pumpkin Fest
Through November 3rd
Homer Glen
With a haunted house for older kids and adults and Fun Barn for the whole family, there’s something for everyone at the old pumpkin farm. Bengston’s features all sorts of activities included pig races, a pumpkin chucker, rides, a petting zoo and more haunted fun!
Fall Arts & Crafts Adventure
September 21st
Hodges Park in Park Ridge
This free outdoor art show will have plenty of works for sale. Come with a full wallet and wall space at home to fill…
Lakeview Taco Fest
September 21st – 22nd
Southport Avenue (from Addison to Roscoe)
Who makes the best taco in town? You’ll likely find out at this event. There will be dozens of tacos to try, live music and even Luchadores! (Mexican Wrestlers). When you’ve tried all the tacos at the fest, make sure to vote for your favorite.
Englewood Jazz Festival
September 21st – 22nd
Hamilton Park in Englewood
This free concert series will feature dozens of acts throughout the weekend.
Northshore Affordable Art Sale
September 21st – 22nd
Westfield Old Orchard Mall in Skokie
Art, live music, kids activities and food will all be available at this free outdoor event.
Riverwalk Fine Art Fair
September 21st – 22nd
Hamilton Park in Englewood
After you’ve heard some music at the Jazz fest, you can take a short trip to the park to see this free art show.
Harvest Pow Wow
September 21st – 22nd
Naper Settlement in Naperville
This Native American fest invites you to celebrate the culture with various activities including dance, music, art, storytelling and shopping.
