Evanston Art & Big Fork Festival - Evanston, IL - Aug 16 to Aug 18, 2019
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 23 to Sep 1, 2019
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 - Aug 30 to Sep 2, 2019
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 - Aug 30 to Aug 31, 2019
Frankfort Fall Festival - Frankfort, IL - Aug 31 to Sep 2, 2019
Each year during Labor Day weekend, over 250,000 visitors gather to the charming Village of Frankfort to enjoy the Frankfort Fall Festival. The festival welcomes over 300 artisans from all over the United States to exhibit their elite products and services. In addition, many of Frankfort’s local organizations collaborate by sponsoring special events that highlight Frankfort Fall Festivities. There is something for everyone from carnival rides to main stage entertainment, to walking tacos and funnel cakes, and more
Septemberfest - Schaumberg, IA - Aug 31 to Sep 2, 2019
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 4 to Sep 8, 2019
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.
Berghoff Oktoberfest - Chicago, IL - Sep 4 to Oct 4, 2019
The annual festival from this longtime favorite German restaurant in Chicago. Keg tapping ceremony. Special menu and beer tasting. Free admission.
Festival of the Vine - Geneva, IL - Sep 6 to Sep 8, 2019
Sample wine and food as you enjoy live music and family fun.
German American Oktoberfest - Chicago, IL - Sep 6 to Sep 8, 2019
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 7 to Sep 7, 2019
Over 15,000 visitors from Northern Illinois and Southern Wisconsin are expected to attend this regional air show.
Mundelein Arts Festival - Mundelein, IL - Sep 7 to Sep 8, 2019
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.
DeKalb Kite Fest - DeKalb, IL - Sep 8 to Sep 8, 2019
Free admission to enjoy the colorful kites that take to the sky, including giant inflatable kites, dancing kites, and stunt kites attract kite enthusiasts and families – bring your own kite or make on there!
Riot Fest - Chicago, IL - Sep 13 to Sep 15, 2019
A three-day music festival featuring various forms of punk at Douglas Park.
Des Plaines Family Festival - Des Plaines, IL - Sep 13 to Sep 15, 2019
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.
Chicago South Asian Film Festival - Chicago, IL - Sep 19 to Sep 22, 2019
The film festival aims to advance diversity in Chicagoland through cinema, conversation, and culture, and gives South Asian talent, stories, and themes a world platform. Held in several venues in downtown Chicago, the festival includes screenings of films, panel discussions, and other opportunities for attendees to connect with filmakers, and attend musical performances, industry workshops, tributes to major artists and awards galas
The Chicago LGBT International Film Festival (Reeling) - Chicago, IL - Sep 19 to Sep 29, 2019
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.
Huntley Fall Fest - Huntley, IL - Sep 20 to Sep 22, 2019
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 Fest - Long Grove, IL - Sep 20 to Sep 22, 2019
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 merchants, three stages of live entertainment, Kid Zone, and more
Oaktoberfest Oak Park - Oak Park, IL - Sep 20 to Sep 21, 2019
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!
Midwest Wizard of Oz Festival - Tinley Park, IL - Sep 21 to Sep 22, 2019
The event, which started in 1982, has been moved to Tinley Park (Chicago) to celebrate the classic American movie, The Wizard of Oz. Vendors, costume characters, speakers, zip line, theater guild, contests, and attractions from Odyssey Fun Farm.
Autumn Fest - Oak Brook, IL - Sep 21 to Sep 21, 2019
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 22 to Sep 22, 2019
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!
Chicago Gourmet - Chicago, IL - Sep 24 to Sep 29, 2019
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.
Grundy County Corn Festival - Morris, IL - Sep 25 to Sep 29, 2019
Parade; Corn, grain, and flower show; hobby and handicraft contest, pie eating contest, and more
ChangeFest Film Festival - Chicago, IL - Sep 28 to Sep 30, 2019
Enjoy films that promote ideas with action.
Walk4Hearing Chicago - Chicago, IL - Sep 28 to Sep 28, 2019
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.
Elim Dutch Festival - Palos Heights, IL - Sep 29 to Sep 28, 2019
Free admission and free parking for a day of fun for the whole family!
Shaw’s Oyster Fest - Chicago, IL - Oct 1 to Oct 31, 2019
30th annual – which is the “Pearl” anniversary! Enjoy fresh oysters and craft beer at this event produced by Shaw’s Crab House. Enjoy a full week of events at their Chicago and Shaumburg locations, including happy hours, pop up 50c oyter hours, slurp-off competitions, and more.
Witches and Warlocks - Schaumburg, IL - Oct 1 to Oct 1, 2019
Come down to the Pat Shepard Center and enjoy a snack and some fun before a photo scavanger hunt around the grounds. All children must be registered – and don’t forget a camera/cell phone for pictures!
Lincoln Square AppleFest - Chicago, IL - Oct 5 to Oct 6, 2019
A Lincoln Square tradition to celebrate fall with local musicians, children’s activities and everything apple!
Lansing Autumnfest - Lansing, IL - Oct 11 to Oct 13, 2019
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.
Scarecrow Festival - St. Charles, IL - Oct 11 to Oct 13, 2019
Award winning event with more than 100+ hand-crafted scarecrows, live entertainment, carnival and craft show.
Chicago Ideas Week - Chicago, IL - Oct 12 to Oct 17, 2019
The world’s largest affordable ideas festival comes to Chicago, with events taking place at Harris Theater, Venue SIX10, and MCA, covering topics that affect Chicago and beyond. Guests can hear from politicians, actors, writers, and many more.
Chicago International Film Festival - Chicago, IL - Oct 16 to Oct 27, 2019
Exhibiting films from around the world for five decades.
Sycamore Pumpkin Festival - Sycamore, IL - Oct 23 to Oct 27, 2019
Annual decorated pumpkin display with parade, carnivals and indoor craft show. The festival started in 1956 to offer a creative outlet for the students of Sycamore has grown into a city wide event
Batfest - Batavia, IL - Oct 26 to Oct 26, 2019
Bataviaâ€™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 22 to Nov 23, 2019
Musical performances and tree-lighting parade with Santa Clause, all along the Magnificent Mile. If you can’t make it, it is televised!