Events · Chicago & Suburbs · October 2026
Your Weekend Guide to Chicago & the Suburbs —
October 2–4, 2026
Happy Wednesday! Get set for a weekend packed with diverse activities across Chicago and its suburbs! From cultural festivals to exciting outdoor events, there's something for everyone to enjoy. Check out the exciting events happening this weekend!
Sumo + Sushi
Spend an unforgettable evening experiencing the excitement, history, and traditions of Japan’s national sport—hosted by sumo legend Konishiki. Through engaging storytelling, live demonstrations, and powerful exhibition matches, you’ll gain a deeper understanding of sumo while witnessing the incredible athleticism of the wrestlers up close.
Lincoln Square Ravenswood Apple Fest 2026
The 39th Annual Apple Fest runs on N. Lincoln Avenue between W. Lawrence and W. Sunnyside Avenues in Lincoln Square. Shop fresh-picked apples, cider and seasonal favorites from Midwest farms, try apple-inspired dishes from local restaurants and food vendors, and sip hard and non-alcoholic ciders and seasonal beers.
Bill Burr
Get ready to laugh! Comedian Bill Burr is bringing his signature stand-up to the Chicago area this week for a series of live shows.
The Chicks: Taking the Long Way 20th Anniversary
Thirteen-time Grammy® Award winners The Chicks celebrate two decades of the critically acclaimed album that topped the Billboard 200 chart and earned The Chicks five Grammy® Awards, including Album of the Year, Record of the Year, and Song of the Year with the Taking the Long Way 20th Anniversary Tour.
DePaul Men's Soccer
Join us as we celebrate the 25th anniversary of Big Vinny, the iconic mural of Saint Vincent de Paul overlooking Wish Field. Created by Brother Mark Elder, Big Vinny has become a beloved symbol of DePaul University and a familiar presence for generations of Blue Demon student-athletes and fans.
West Town Art Walk
Celebrate Chicago’s creative community at the 16th Annual West Town Art Walk, a free, neighborhood-wide celebration featuring local artists, galleries, small businesses, music, food and special promotions throughout West Town.
Family Fall Night
Spend the evening exploring the corn maze, enjoying the farm activities, gathering around the bonfires, and listening to live music as the sun goes down. We’ll be grilling up food, making s’mores, and serving plenty of your favorite TOM’S fall treats and drinks available for purchase.
Touch-A-Truck
Grab a hard hat and join us for this free family event that allows children to see, touch and explore a variety of trucks and emergency vehicles from our Public Works and Public Safety fleets. Please note that this event includes many loud noises, horns and sirens, but the last hour of the event will be a “sensory hour” with no lights, sirens or horns. Activities for kids include painting and naming a vehicle in the Village's fleet, riding in the aerial truck (waiver required), and more!
Cider and Ale Festival
This fall, treat yourself to a curated selection of hard cider and seasonal beer from more than 30 local breweries and cideries at the Cider and Ale Festival. Take in the crisp autumn air as you sip and stroll through The Morton Arboretum’s stunning tree-filled landscapes.
Northbrook Autumnfest 2026
Celebrate the season with this free family event at Northbrook Autumnfest! Enjoy a variety of activities, including bounce houses, pumpkin chucking, arts and crafts, a horse trolley, a petting zoo, free pumpkins (one per child attendee, while supplies last), apple cider, food trucks, and Culinary Gangster.
Downtown Wheaton Chili Cookoff
The Chili Cookoff returns to Downtown Wheaton this October! Your favorite downtown eateries compete for your vote with their unique spin on this fan-favorite dish. Ticketholders will enjoy unlimited chili tastings before voting on the tastiest recipe. Don't miss this festive fall event—admission includes live music and unlimited tastings, so bring your appetite. This event will sell out, so buy your tickets now!
Bears Backyard Tailgate
Join fellow fans at Washington Park as the Bears take on the competition live on a giant outdoor screen, sponsored by Pixel Fleet. Bring your favorite tailgate setup and enjoy an afternoon of football, food, and fun. During halftime and commercial breaks, keep the excitement going with football-themed games, contests, and activities for fans of all ages.
Allie Payne Group at Compass
Enjoy Your Weekend —
And If Home Is on Your Mind, Let's Talk.
Whether you're exploring a new neighborhood this weekend or thinking about what comes next, we're always here to help you navigate it.
