Evanston Art & Big Fork Festival - Evanston, IL - Aug 21 to Aug 23, 2020
A weekend-long celebration of local art and flavorful fare including painting, sculpture, and photography along with handmade jewelry, one-of-a-kind furniture, and home accessories.
Chicago Jazz Festival - Chicago, IL - Aug 28 to Sep 6, 2020
Free live jazz music by local and national artists in Millenium Park and venues across the city over Labor Day weekend.
Taste of Polonia - Chicago, IL - Sep 4 to Sep 7, 2020
This annual Labor Day weekend festival at the Copernicus Center in Chicago’s Jefferson Park offers live music, Polish food, and fun for four days.
North Coast Music Festival - Chicago, IL - Sep 4 to Sep 6, 2020
Septemberfest - Schaumberg, IA - Sep 5 to Sep 7, 2020
Arts & crafts show, craft beer & wine tent, carnival, 3 stages of live entertainment, Taste of Schaumburg, parade, fireworks and more at the municipal center on Schaumburg Ct. Free admission
Sandwich Fair - Sandwich, IL - Sep 9 to Sep 13, 2020
The Dekalb County fair is the oldest continuing fair in the State of Illinois. It is also the largest display of agricultural and home arts exhibits in the Midwest. Since 1888.
Riot Fest - Chicago, IL - Sep 11 to Sep 13, 2020
A three-day music festival featuring various forms of punk at Douglas Park.
Festival of the Vine - Geneva, IL - Sep 11 to Sep 13, 2020
Sample wine and food as you enjoy live music and family fun.
German American Oktoberfest - Chicago, IL - Sep 11 to Sep 13, 2020
A parade, German hospitality, food and fun hosted by the United German-American Societies of Greater Chicago at Lincoln Square
Wings Over Waukegan - Waukegan, IL - Sep 12 to Sep 12, 2020
Over 15,000 visitors from Northern Illinois and Southern Wisconsin are expected to attend this regional air show.
Mundelein Arts Festival - Mundelein, IL - Sep 12 to Sep 13, 2020
A two-day juried art event with tasty food, local musicians and 45 top artists, plus artwork from local high school students, all at Kracklauer Park.
Des Plaines Family Festival - Des Plaines, IL - Sep 18 to Sep 20, 2020
Free admission, musical entertainment and parking at this Lake Park fair with carnival, KidZone, car show, festival food, pie eating contest and open air market.
Oaktoberfest Oak Park - Oak Park, IL - Sep 18 to Sep 19, 2020
Celebrate the changing seasons at Oaktoberfest! Enjoy a premier music line up, delicious fall foods, specialty craft beers, and a kids’ root beer garden! Free admission!
Autumn Fest - Oak Brook, IL - Sep 19 to Sep 19, 2020
Fun for all, with live music, kids’ activities including a magician, food vendors, beer and wine, and the Wagon N’ Wine Tour, a wagon ride with a glass of wine!
Pere Marquette Lodge Apple Festival - Grafton, IL - Sep 20 to Sep 20, 2020
Warm apple pie, hand-dipped caramel apples, handmade crafts, live music and fresh produce are just a few of the offerings at the Apple Festival at Pere Marquette. The festivities also includes apple wine tasting, kid’s activities and restaurant favorites. An apple pie walk (similar to a cake walk) will be held where visitors will purchase tickets and take a walk for a chance to take home a fresh baked apple pie. Proceeds for the apple pie walk will be donated to the Friends of Pere Marquette Foundation. The Lodge also hosts the annual Pumpkin Roll. Participants can bring their own pumpkin or purchase one at the festival to decorate for a competitive roll down the hill in front of the Lodge. Second and third place participants will win gift certificates for the Restaurant and the fastest pumpkin will win the grand prize of a free nights stay at the historic Lodge. Best of all, there’s free admission!
The Chicago LGBT International Film Festival (Reeling) - Chicago, IL - Sep 24 to Oct 4, 2020
The first Chicago LGBTQ+ International Film Festival took place in April 2018 in a 90-seat folding-chair screening room, with nearly every screening sold out. The demand and enthusiasm for the festival made it an annual event that has been going strong ever since. The mission of Reeling is to recognize the important artistic contributions that lesbian, gay, bisexual, and transgender filmmakers have made, educate the general population, and investigate the history of LGBTQ+ film, and to counteract this sterotyping with valid, meaningful and diverse portrayals of those in the LGBTQ+ community.
Chicago Gourmet - Chicago, IL - Sep 25 to Sep 27, 2020
Celebrate food and wine in downtown Chicago with this Bon Appetit event featuring more than 100 wineries, breweries and spirit makers as well as more than 150 top restaurants and chefs.
Lansing Autumnfest - Lansing, IL - Sep 25 to Sep 27, 2020
Over 20,000 people come out each year to enjoy a weekend of great food, children’s activities, military tribute, a Marketplace, beer garden, and 2 stages of live entertainment.
Huntley Fall Fest - Huntley, IL - Sep 25 to Sep 27, 2020
A three day community celebration with entertainment, a beer garden, food vendors, a full carnival midway, plenty of fall activities, and a spectacular fireworks display on Saturday night! Free admission!
Long Grove Apple Festival - Long Grove, IL - Sep 25 to Sep 27, 2020
Welcome Autumn with this annual apple festival! From apple popcorn to apple lattes, enjoy hundreds of apple-inspired treats, a pop-up apple orchard with local merchangs, three stages of live entertainment, Kid Zone, and more
Elim Dutch Festival - Palos Heights, IL - Sep 26 to Sep 26, 2020
Free admission and free parking for a day of fun for the whole family!
Walk4Hearing Chicago - Chicago, IL - Sep 26 to Sep 26, 2020
Empowers and inspires those affected by hearing loss while raising money for national and local programs that provide information, education, support, and advocacy. Vendors will be on site to provide resources for individuals and families affected by hearing loss.
Lincoln Square AppleFest - Chicago, IL - Oct 3 to Oct 4, 2020
A Lincoln Square tradition to celebrate fall with local musicians, children’s activities and everything apple!
Scarecrow Festival - St. Charles, IL - Oct 9 to Oct 11, 2020
Award winning event with more than 100+ hand-crafted scarecrows, live entertainment, carnival and craft show.
Chicago International Film Festival - Chicago, IL - Oct 14 to Oct 25, 2020
Exhibiting films from around the world for five decades.
Batfest - Batavia, IL - Oct 31 to Oct 31, 2020
Batavia’s annual Halloween themed family event attracts over 2,500 for downtown trick-or-treating, parade, pumpkin bowl, contests, art, games, and more
The Magnificent Mile Festival of Lights - Chicago, IL - Nov 20 to Nov 21, 2020
Musical performances and tree-lighting parade with Santa Clause, all along the Magnificent Mile. If you can’t make it, it is televised!