Events · Chicago & Suburbs · October 2026
Your Weekend Guide to Chicago & the Suburbs —
October 9–11, 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!
Chicago Fashion Week
Now in its third year, Chicago’s Fashion Week showcases the city’s creativity, culture, and couture.
Lincoln Park Wine Fest
The 10th annual Lincoln Park Wine Fest is a can’t-miss event for wine lovers, with wine tastings, local food vendors, and stunning fall vibes.
Chicago Blackhawks vs Carolina Hurricanes
Hockey is back! Come see the Blackhawks take on the Carolina Hurricanes.
Bank of America Chicago Marathon
Over 55,000 runners will partake in this special event. This is 1 of only 7 World Marathon Majors with 1.7 million estimated annual spectators.
If You Give a Mouse a Cookie
Do not give this Mouse a cookie! Because if you do, you’re in for milk, messes, and wildly entertaining mayhem! YPT launches its milestone 5th Anniversary Season with a fast-paced, cookie-fueled celebration of theatrical imagination, laughter, and joyful bedlam. Bring the whole family for some mouse-sized mischief—and get ready to laugh your whiskers off!
Olivia Rodrigo: The Unraveled Tour
The Unraveled Tour follows the success of Olivia Rodrigo’s 2022 debut, The SOUR Tour, and her first headline arena run, the GUTS world tour, which spanned more than 60 cities across 20+ countries throughout 2024 and 2025. The GUTS world tour marked her largest tour to date, with 95 sold-out shows and over 1.4 million fans in attendance.
Fall Festival
Don't miss the Forest Preserve District’s largest event of the year! Festivities will include trick riding, vaulting, carriage driving, a drill team, and equine therapy demonstrations by various performers. Families can enjoy wagon rides, pony rides, barn tours, hands-on nature activities, and more.
Autumn Harvest Fest
Don’t miss fall family fun with crafts, games, hayrides, a scarecrow building contest, live music and entertainment, and food available for purchase from Garibaldi’s Pizza, Kori’s Koop and Poppin’ T’s Kettlecorn.
Northwestern vs Ball State
The Northwestern Wildcats host The Ball State Cardinals. The Wildcats offer some of the best Division 1 college sports action in the Midwest, featuring 12 teams competing in the Big Ten Conference.
Dinner Detective Murder Mystery
The Dinner Detective is an interactive true crime mystery show set in the present day and based on real cold cases. Feast on a fantastic dinner, but just beware... the killer is hiding somewhere in the room, and you may find yourself as a Prime Suspect. Our Detectives proceed to interrogate everyone in attendance and discover clues as more victims are revealed. At the end of the night, prizes are awarded to the Top Sleuth who solves the crime!
Mocktoberfest
Ticket includes unlimited 3-oz samples of NA beverages, including limited-edition Oktoberfest NA beer drops, zero-proof cocktails, teas & more. Enjoy a local vendor market featuring Chicago-area makers and small businesses, live music with rock/pop energy and just enough polka to keep things festive, plus Oktoberfest-style seating, décor, and table games.
Fall-A-Palooza
Celebrate the best of the season at Fall-A-Palooza 2026 — your ultimate autumn adventure for the whole family! Join us for a festive day packed with fall favorites and outdoor fun!
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.
