Evanston Art & Big Fork Festival - Evanston, IL - Aug 13 to Aug 15, 2021
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 Gourmet - Chicago, IL - Sep 1 to Sep 30, 2021
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.
North Coast Music Festival - Chicago, IL - Sep 3 to Sep 5, 2021
Chicago Jazz Festival - Chicago, IL - Sep 4 to Sep 18, 2021
On hiatus for 2021 – enjoy a few hours of jazz (9/4) and blues (9/18) at Jay Pritzker Pavilion. Normally: Free live jazz music by local and national artists in Millenium Park and venues across the city over Labor Day weekend.
Frankfort Fall Festival - Frankfort, IL - Sep 4 to Sep 6, 2021
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 - Sep 4 to Sep 5, 2021
Celebrating 50 years in 2022. 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 8 to Sep 12, 2021
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.
Festival of the Vine - Geneva, IL - Sep 10 to Sep 12, 2021
Sample wine and food as you enjoy live music and family fun.
German American Oktoberfest - Chicago, IL - Sep 10 to Sep 12, 2021
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 11 to Sep 11, 2021
Over 15,000 visitors from Northern Illinois and Southern Wisconsin are expected to attend this regional air show.
Mundelein Arts Festival - Mundelein, IL - Sep 11 to Sep 12, 2021
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 12 to Sep 12, 2021
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 16 to Sep 19, 2021
A three-day music festival featuring various forms of punk at Douglas Park.
Des Plaines Family Festival - Des Plaines, IL - Sep 17 to Sep 19, 2021
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.
Autumn Fest - Oak Brook, IL - Sep 18 to Sep 18, 2021
For 2021: Join the Autumn Fest fun early – at 1:30pm there will be Ribbon Cutting Ceremony at the north area of Central Park to celebrate the completion of Phase 1 construction! This free, family-friendly event will start with kid entertainment from 2-3:30pm with a DJ, juggler, face painter, carnival games, arts & crafts, hayrides, and more! Feel Good Party Band will be on stage performing from 3:30-5pm. All the while there will be food, beer, and wine available for purchase.
Pere Marquette Lodge Apple Festival - Grafton, IL - Sep 19 to Sep 19, 2021
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!
Grundy County Corn Festival - Morris, IL - Sep 22 to Sep 26, 2021
Parade; Corn, grain, and flower show; hobby and handicraft contest, pie eating contest, and more
Huntley Fall Fest - Huntley, IL - Sep 23 to Sep 26, 2021
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!
The Chicago LGBT International Film Festival (Reeling) - Chicago, IL - Sep 23 to Oct 7, 2021
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.
Lansing Autumnfest - Lansing, IL - Sep 24 to Sep 26, 2021
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.
Long Grove Apple Festival - Long Grove, IL - Sep 24 to Sep 26, 2021
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
Oktoberfest Chicago - Chicago, IL - Sep 24 to Sep 26, 2021
Featuring handmade bratwurst, cold beer and authentic German music, this popular Chicago Oktoberfest hosted by St. Alphonsus Church. Received a 10Best Reader’s Choice Award from USA Today in 2015. Adult admission is $5-10.
Elim Dutch Festival - Palos Heights, IL - Sep 25 to Sep 25, 2021
Free admission and free parking for a day of fun for the whole family!
Chicago South Asian Film Festival - Chicago, IL - Sep 25 to Oct 2, 2021
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
Revolution Oktoberfest - Chicago, IL - Sep 25 to Sep 25, 2021
Head to Revolution Brewing’s Taproom for a fun day of games, contests, music, food, and of course — German beer!
Hyde Park Jazz Festival - Chicago, IL - Sep 25 to Sep 26, 2021
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. We do this by creating opportunities for a diverse community of listeners to engage with the music and its creators, and by working with artists, organizational partners and networks to celebrate the rich tradition of jazz and to support the development of new work and ideas.
Walk4Hearing Chicago - Chicago, IL - Sep 26 to Sep 26, 2021
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.
Chicago Half Marathon and 5k - Chicago, IL - Sep 26 to Sep 26, 2021
Take in breathtaking cityscape views, lakefront breezes, vibrant neighborhoods and the beauty of the Windy City in the fall. Earn a HUGE finisher medal and relish in your post race glory at the Chi town infused finish line festival.
Lincoln Square AppleFest - Chicago, IL - Oct 2 to Oct 3, 2021
A Lincoln Square tradition to celebrate fall with local musicians, children’s activities and everything apple!
Scarecrow Festival - St. Charles, IL - Oct 8 to Oct 10, 2021
Award winning event with more than 100+ hand-crafted scarecrows, live entertainment, carnival and craft show.
Highwood Pumpkin Festival - Highwood, IL - Oct 8 to Oct 10, 2021
This fan favorite event is held to not only break the Guinness World Record of 30,581 for most pumpkins carved in one place, but to take it a step further by lighting a pumpkin for everyone affected by autism in Illinois- a staggering 52,000 individuals! Imagine pumpkins lining the streets on scaffolding towering over 30 feet lit and synced to music. It’s a site to behold and the ultimate family event!
Chicago Marathon - Chicago, IL - Oct 10 to Oct 10, 2021
The Bank of America Chicago Marathon is known for its flat and fast course. The race starts and finishes in Grant Park and travels through one of the world’s most magnificent cities. The course has produced four world records, several national records and countless personal bests. Runners enjoy the support of 1.7 million spectators as they run through 29 neighborhoods.
Chicago International Film Festival - Chicago, IL - Oct 13 to Oct 24, 2021
Exhibiting films from around the world for five decades.
Wizard World Comic Con Chicago - Rosemont, IL - Oct 15 to Oct 17, 2021
Harvest Celebration at Heritage Farm - Schaumburg, IL - Oct 17 to Oct 17, 2021
Sycamore Pumpkin Festival - Sycamore, IL - Oct 27 to Oct 31, 2021
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 30 to Oct 30, 2021
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 19 to Nov 20, 2021
Musical performances and tree-lighting parade with Santa Clause, all along the Magnificent Mile. If you can’t make it, it is televised!
ZooLights at Lincoln Park Zoo - Chicago, IL - Nov 19 to Jan 2, 2022
Mesmerizing light display at the zoo. Chicago’s favorite holiday tradition is back and better than ever in 2021 with the new Pepper Family Wildlife Center at the heart of the zoo, a new holiday lights experience on the Main Mall, and an exciting new light show on the South Lawn. Also new this year: sensory-friendly visit times and an impressive 18-foot holiday tree sure to inspire festive oohs and aahs. Members only nights, free and $5 admission nights, sensory friendly nights, and other special events.
Thanksgiving Eve at Howl at the Moon Chicago - Chicago, IL - Nov 24 to Nov 24, 2021
Turkey is good, but booze is better! Celebrate the long holiday weekend with some live music, dancing and drinks, with featured drinks, games, dancing and a great night out!
Chicago Thanksgiving Parade - Chicago, IL - Nov 25 to Nov 25, 2021
Turkey Day 5K/8K Trot - Chicago, IL - Nov 25 to Nov 25, 2021
Supporting the Greater Chicago Food Depository, you will join fellow runners, joggers and walkers in some light hearted fun while ensuring no Chicagoan will go hungry this holiday season.
Dan Gibbons Turkey Trot - Elmhurst, IL - Nov 25 to Nov 25, 2021
5k fundraiser run on Thanksgiving. To date, The Dan Gibbons Foundation has donated nearly $3.9 million dollars and keeps all funds raised within the County of DuPage
North Shore Turkey Trot - Highland Park, IL - Nov 25 to Nov 25, 2021
5k and 10k on Thanksgiving
Turkey Trot 5 Mile Run - Glen Ellyn, IL - Nov 25 to Nov 25, 2021
Get active for a good cause by starting your Thanksgiving at the Turkey Trot 5-Mile Predicto Race! The top two runners who most accurately predict their finish time will win a Thanksgiving treat. Prizes will also be awarded for Best Costume. The Turkey Trot is free and open to the public
Chicago Tardis - Lombard, IL - Nov 26 to Nov 28, 2021
Held since 2000, this festival is held by fans, for fans of both the new and classic Doctor Who series, and features panels, parties, and more. The event includes guests who were stars from the show, including 2019 guest Tosin Cole, who played the thirteenth Doctor’s companion, Ryan Sinclair. Tickets are available for single-day admission for both adults and children,plus weekend access, VIP, and more, so you can choose your experience!
Grant Park Turkey Trot 5K - Chicago, IL - Nov 27 to Nov 27, 2021
5K and 10K at Grant Park with Do-Rite Donuts waiting for you at the finish line.
Taste of Polonia - Chicago, IL - Sep 2 to Sep 5, 2022
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.