Schaumburg Senior Expo (Schaumburg): Free

  • Date: Tuesday, September 15, 2026 (10 AM–1 PM)

  • Venue: Schaumburg Sport Center, 1141 West Irving Park Road, Schaumburg, IL 60193

  • This free resource expo connects older adults, caregivers, and families with local businesses and organizations offering wellness information, senior services, health-related resources, and community support. It is designed as a practical one-stop information event, with exhibitors and service providers available for direct conversations and referrals.

Happy Times Pumpkin Fest (Lincolnshire): Free

  • Date: Wednesday, September 16 – Saturday, October 31, 2026, 10 AM - 6 PM (Closed Tuesdays)

  • Venue: Didier Farms, 16678 Aptakisic Rd., Lincolnshire, IL 60069

  • Enjoy a classic fall day with pumpkin picking, a corn maze, Pumpkin Playland, Animal Land Zoo, amusement rides, pony and camel rides, fall treats, apple cider donuts, and more. Admission and parking are free; individual attractions require tickets.

Fall Food Truck Festival 2026 (Bartlett): Free

  • Date: Thursday, September 17, 2026 (5 PM – 9 PM)

  • Venue: Hanover Township, 250 Illinois Route 59, Bartlett, IL 60103

  • Bartlett’s Fall Food Truck Festival is a free-admission evening event centered on food-truck dining at Hanover Township. The official Village calendar confirms the date and hours; vendor lineup, entertainment, and activity details should be checked again close to the event date.

3rd Annual Fall Resource Fair (Elgin): Free

  • Date: Thursday, September 17, 2026 (5 PM - 7 PM)

  • Venue: Centre of Elgin, Heritage Ballroom, 100 Symphony Way, Elgin, IL 60120

  • Connect with local organizations and discover community resources and services at this free family literacy and resource fair hosted by The Literacy Connection.

Oktoberfest (Crystal Lake) :$8

  • Date: Friday, September 18 – Saturday, September 19, 2026 (Friday 3 PM - 11 PM, Saturday 1 PM - 11 PM)

  • Venue: Crystal Lake Brewing, 150 N. Main St., Crystal Lake, IL 60014

  • Enjoy Oktoberfest celebrations with live music, food trucks, and a festive atmosphere at Crystal Lake Brewing. The $8 cover includes a take-home 1/2-liter stein.

Sketchbook Brewing Annual Oktoberfest (Skokie): Free

  • Date: Friday, September 18 – Sunday, September 20, 2026 (Friday 11 AM - 8 PM, Saturday 11 AM - 8 PM, Sunday 11 AM - 8 PM)

  • Venue: Sketchbook Brewing Co., 4901 Main St., Skokie, IL 60077

  • Enjoy a festive weekend with food trucks, live music, games, and family-friendly activities, including a kids’ fall art activity Saturday and Sunday from 2–4 PM.

Plein Air Festival (Arlington Heights): Free

  • Date: Friday, September 18 – Sunday, September 27, 2026

  • Venue: Outdoor locations throughout Arlington Heights

  • Watch local artists bring Arlington Heights to life through outdoor painting, creating original artwork inspired by the community and its surroundings. The festival gives art lovers a chance to see artists working on location and explore finished pieces created during the event. Original artwork will also be available for purchase.

Rotary Club of Palatine Oktoberfest (Palatine): Free

  • Date: Friday, September 18 – Sunday, September 20, 2026 (Friday 5 PM - 12 AM, Saturday 12 PM - 12 AM, Sunday 12 PM - 6 PM)

  • Venue: Downtown Palatine, Smith and Slade Streets, Palatine, IL 60067

  • Enjoy a family-friendly Oktoberfest celebration featuring live German music, traditional food, a large outdoor gathering area, and plenty of festive fall atmosphere throughout downtown Palatine. Saturday is Family Day with activities geared toward younger visitors.

Fall Fest (Des Plaines): Free

  • Date: Friday, September 18 – Sunday, September 20, 2026 (Friday 6 PM - 11 PM, Saturday 12 PM - 11 PM, Sunday 12 PM - 7 PM)

  • Venue: Lake Park, 2200 Lee St., Des Plaines, IL 60018

  • A major three-day community harvest festival set alongside scenic Lake Opeka featuring a full carnival midway with rides and games for all age levels. The event includes a live entertainment stage headlined by Hillbilly Rockstarz and ARRA, a KidZone with a petting zoo and pumpkin painting, local civic sponsor booths, and an array of food and beer concessions.

Elk Grove Village Oktoberfest (Elk Grove Village): Free

  • Date: Friday, September 18 – Saturday, September 19, 2026 (Friday 6 PM - 10:30 PM, Saturday 3 PM - 11 PM)

  • Venue: Rotary Green, 164 Lions Dr., Elk Grove Village, IL 60007

  • A lively Bavarian-style community festival featuring authentic German beer, Bavarian pretzels, and specialties under an expansive tent. Live traditional music is led by Die Musikmeisters, while Saturday afternoon hosts the FamilyFest with free bounce attractions, games, and kid-friendly entertainment.

Mount Prospect Downtown Oktoberfest & Fall Festival (Mount Prospect): Free

  • Date: Friday, September 18 – Saturday, September 19, 2026 (Friday 4 PM - 11 PM, Saturday 1 PM - 11 PM)

  • Venue: Downtown Mount Prospect (Intersection of Emerson St. & Busse Ave.), Mount Prospect, IL 60056

  • The Mount Prospect Downtown Merchants Association presents a two-day autumn festival celebrating local heritage. Friday and Saturday evenings highlight German culture with bratwurst, pretzels, Oktoberfest beers, and live polka/German music from bands like Paloma. Saturday afternoon is dedicated to family fun with pony rides, hayrides, crafts, pumpkin decorating, and a root beer garden.

Sim Gaming Expo (Schaumburg): $35+

  • Date: Friday, September 18 – Sunday, September 20, 2026 (Friday 12 PM - 8 PM, Saturday 10 AM - 6 PM, Sunday 10 AM - 5 PM)

  • Venue: Schaumburg Renaissance Convention Center, 1551 Thoreau Dr. N., Schaumburg, IL 60173

  • Experience a weekend dedicated to simulation gaming, featuring the latest sim racing, flight simulation, and VR technology, hands-on demos, competitions, exhibitors, content creators, and industry panels.

Brews, Blues, & BBQ (Wood Dale): Free

  • Date: Friday, September 18, 2026 (5 PM - 8 PM)

  • Venue: White Oaks Park, 111 S. Wood Dale Rd., Wood Dale, IL 60191

  • Enjoy an evening of live blues music, BBQ, and a relaxed outdoor festival atmosphere at White Oaks Park, featuring live music from Andrew Diehl at 6 PM.

Elgin Short Film Festival (Elgin): $11.50+

  • Date: Saturday, September 19, 2026 (6 PM - 9:30 PM)

  • Venue: The Hemmens Cultural Center, 45 Symphony Way, Elgin, IL 60120

  • Enjoy an evening celebrating independent filmmaking with a premiere-style red carpet, pre-show entertainment, screenings of the top six short films from filmmakers around the U.S. and beyond, and live audience voting for the People’s Choice Award. Bar and concessions will be available.

4th Annual Pepper Road Fall Fest & Barn Fest (Lake Barrington): Free

  • Date: Saturday, September 19, 2026 (11 AM - 3 PM)

  • Venue: N. Pepper Road Business Corridor, Lake Barrington, IL 60010

  • Celebrate the start of fall with a community-wide autumn block party featuring a large artisan market, vintage and resale finds, the annual Barn Fest at All American Reclaim, food trucks, live classic rock, interactive games, and an open house hosted by the Barrington Countryside Fire District.

Heritage Fest (Arlington Heights): Free

  • Date: Saturday, September 19, 2026 (9 AM - 12 PM)

  • Venue: Arlington Heights Historical Museum, 110 W. Fremont St., Arlington Heights, IL 60004

  • Celebrate the cultural diversity of Arlington Heights with live music and dance performances, cultural exhibits and demonstrations, international food, and activities from local cultural organizations. The Arlington Heights Farmers Market will also be open nearby during the event.

Fall Fest (Carpentersville): Free

  • Date: Saturday, September 19, 2026 (11 AM - 3 PM)

  • Venue: Carpenter Park, 300 Carpenter Blvd., Carpentersville, IL 60110

  • Enjoy a fall afternoon with 50+ local vendors, handmade goods, food and treats, kids’ attractions, fall activities, and a DJ creating a fun community atmosphere.

Heritage Fest Artisan Fair (West Dundee): Free

  • Date: Friday, September 18 – Sunday, September 20, 2026 (Friday 6 PM - 11 PM, Saturday 10 AM - 6 PM, Sunday 10 AM - 5 PM)

  • Venue: N. Third St. & Lincoln Ave., West Dundee, IL 60118

  • Browse handcrafted work from approximately 90 artisans, including jewelry, stained glass, apparel, paper crafts, metal art, woodwork, soaps, honey products, and more, along with food, entertainment, and family activities.

15th Annual Mundelein Fine Arts Festival (Mundelein): Free

  • Date: Saturday, September 19 – Sunday, September 20, 2026 (10 AM - 5 PM)

  • Venue: Courtland Commons, 431 N. Lake St., Mundelein, IL 60060

  • Browse original artwork from approximately 50 juried fine artists and craftspeople, while enjoying live music, food, and a variety of artwork across different mediums. The festival also features student artwork from local high schools.

All Things Aquascaping Aquatic Plant Sale (Lake Zurich): Free

  • Date: Saturday, September 19, 2026, beginning at 9:00 AM to noon

  • Venue: American Legion Post 964, 51 Lions Drive, Lake Zurich, IL 60047

  • All Things Aquascaping is a specialty aquatic-hobby market and workshop featuring aquatic and terrarium plants sold directly by local growers, small tropical fish, hardscape materials, aquarium supplies, and aquascaping products. The free all-ages event also includes aquascaping workshops and supports the group’s project to build an aquarium for the Lake Zurich American Legion; free parking is available.

Harvest & Hops Fall Festival (Crystal Lake): $5

  • Date: Saturday, September 19, 2026 (3 PM - 10:30 PM)

  • Venue: The Dole, 401 Country Club Road, Crystal Lake, IL 60014

  • Set against the historic backdrop of The Dole landmark property, this family-friendly autumn festival blends seasonal harvest fun with a craft beer showcase. The event grounds feature live music, local craft vendors, a public pumpkin patch, and a highly interactive children's petting zoo. Adults can purchase tickets for an immersive beer-tasting experience highlighting unique seasonal releases from four prominent regional craft breweries.

Be The One Expo (Des Plaines): Free

  • Date: Sunday, September 20, 2026 (10:30 AM–5 PM)

  • Venue: The GENCenter, formerly the Des Plaines Elks Lodge, 52 East Northwest Highway, Des Plaines, IL 60016

  • Hosted by American Legion Auxiliary Unit 36 in partnership with Des Plaines American Legion Post 36, this free community resource expo centers on suicide prevention, mental-health awareness, veteran and military-family support, caregiver resources, and connection to local service providers. The event honors people lost to suicide while encouraging attendees, businesses, and organizations to support the American Legion’s “Be The One” message: notice someone in need, ask, listen, and help connect them to assistance.

JapanFest NW (Hoffman Estates): Free

  • Date: Sunday, September 20, 2026 (1 PM - 4 PM)

  • Venue: Hideaway Brew Garden, Village Green, 5510 Prairie Stone Pkwy., Hoffman Estates, IL 60192

  • Experience Japanese culture through live performances, martial arts demonstrations, calligraphy, origami, anime drawing, traditional arts, and other hands-on activities for the whole family.

Craft & Vendor Fair (Mount Prospect): Free

  • Date: Sunday, September 20, 2026 (10 AM - 4 PM)

  • Venue: Prospect Moose Lodge #660, 601 N. Main St., Mount Prospect, IL 60056

  • Browse a variety of handmade crafts, unique gifts, and products from local vendors while supporting small businesses and makers.

Fallapalooza (Wheeling): Free

  • Date: Sunday, September 20, 2026 (1 PM – 5 PM)

  • Venue: Heritage Park Performance Pavilion, 100 Community Boulevard, Wheeling, IL 60090

  • Wheeling’s Fallapalooza is a family-oriented fall afternoon with carnival-style games, hayrides, inflatables, pumpkin decorating, and other kid-friendly activities. The Park District lists the event among its free community programs, making it a strong no-cost fall option for families.