20+ things to do in Chicago this October

October is upon us, which means it’s time to break out the cozy scarf and boots to enjoy some of the city’s finest fall festivities. While this season may look different from years past, there are still plenty of ways to celebrate the arrival of sweater weather in Chicago. From drive-in film festivals and Halloween celebrations to a historic art exhibit, socially distanced fall fest, and more, here are our top picks for Chicago activities to enjoy this October.

Run a safe 5K through gorgeous fall foliage

Photo courtesy Morton Arboretum

The Morton Arboretum in Lisle is the perfect fall backdrop for a socially distanced Fall Color 5K run and walk. On Oct. 3 and 4, you can choose to participate in a safe 5K course throughout the park or run virtually in support of the Arboretum’s efforts to protect and plant hundreds of trees. The race starts at 7 a.m. and runners will be safely distanced to ensure safety protocols are kept in place. Register for the race here.

Check out a movie (or three) at a fall film festival

Photo by Jona

This October, multiple exciting film festivals bring new films for streaming and drive-in movie experiences across Chicago. The 56th annual Chicago International Film Festival is North America’s largest international film fest, sharing over 100 films in both virtual and drive-in experience format.

Check out other Chicago film festivals this month:

South Side Film Festival: Celebrate the city’s South Side on film with shorts, documentaries, animation and music videos available for streaming now through Oct. 4.
Reeling: The Chicago LGBTQ+ International Film Festival: This annual fest highlights a variety of LGBTQ+ films and videos for moviegoers virtually through Oct. 4.
Asian Pop-Up Cinema: For their 11th season, Asian Pop-Up Cinema is hosting a hybrid film festival with online and in-person screenings through Oct. 31.
Chicago Festival of Israeli Cinema: One of just a few all-Israeli film fests in the country, the online event includes documentaries, feature films, shorts, and more.

Listen to live music under the stars

The Lakeshore Drive-In has created a space for Chicagoans to enjoy live music safely. Enjoy a variety of live music shows from the comfort of your car with incredible skyline views to boot. The drive-in is located at the Adler Planetarium and events are Thursday through Sunday nights all month long. Tickets start at $160 for four tickets and a car pass. Learn more about the events and get your ticket.

Learn food and drink tips from Chicago’s best chefs

Foodies rejoice: Fulton Market will be transformed into Harvest Fest: A Socially Distanced Celebration from Oct. 15 – 18. Led by chef Stephanie Izard, the all-outdoor weekend will include an all-star cast of Chicago chefs, including Sarah Grueneberg, Brian Jupiter, Rick Bayless, Paul Kahan, and more.

The weekend’s events include live cooking demonstrations, exclusive chef-led meals, beverage classes, wine tastings, and more. Check out the full lineup of events here and reserve your ticket in advance to enjoy the fall-themed food and beverage fun.

Explore the art of Claude Monet

Claude Monet. Water Lily Pond, 1900. The Art Institute of Chicago, Mr. and Mrs. Lewis Larned Coburn Memorial Collection.

The Art Institute is proudly home to the largest collection of work by Claude Monet outside of Paris. The new unique exhibit, Monet and Chicago, showcases over 70 pieces of work, including paintings and drawings that span the artist’s lifelong career heralded as the Father of Impressionism. Social distancing protocols are in place and the exhibit requires a $7 ticket purchased in advance.

Head to the drive-in for Halloween favorites

One of Lakeview’s most popular movie theatres, the Music Box Theatre, will be trading its annual 24-hour movie marathon “Music Box of Horrors” for a month-long drive-in movie experience, titled 31 Nights of Drive-In Terror. The theatre will take over the Chi-Town Movies Drive-In all month long to showcase spooky favorites such as Carrie, Nightmare on Elm Street, The Texas Chainsaw Massacre and more. Get your tickets here.

Enjoy a circus show in the park

Who said circus shows were only made for tents? Midnight Circus brings the high-flying adventure to a local level, with intimate circus performances at Welles Park in Lincoln Square on Oct. 3 and Douglass Park in Lawndale on Oct 10. The fun and whimsical 45-minute show is free for admission, but does require online reservations for seats to ensure proper social distancing. Browse shows and reserve your seat here.

Stock up on fall’s best produce

Photo by Bozhin Karaivanov

Lincoln Square’s Apple Fest may look a little different from last year, but that doesn’t mean you need to be deprived of the season’s crisp apples, craft cider, and artisan goods. This year, Apple Fest has gone fully virtual with an online market of produce and packages available for purchase. Additionally, there will be a weekend farmers market on Oct. 3rd and 4th where items will be available for pre-order and pick-up.

Taste some of Chicago’s best wings

If you’re a fan of wings (and who isn’t come football season?) you’ll want to mark your calendars for WingOut Chicago. Starting on Oct. 14 and continuing weekly through November, you can enjoy endless wings with drink specials, a rating card and more from a lineup of Chicago’s top wing providers. The featured restaurants include Broken Barrel Bar, OG’s, Woodie’s, Joe’s on Weed, and Whiskey Business.

Check out more exciting October events: