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What to Do in Chicago During Fall

A guide of what to do in Chicago during the fall, one of the best times of year to visit the city.

Fall is one of the best times of the year to visit Chicago. The weather is warm without being too hot. Many of Chicago’s summer activities can still be enjoyed in the early fall. When the weather gets cooler, there are opportunities to go apple picking and to visit pumpkin patches.

Last updated: May 2022

What to Do in Chicago During Fall:

Seasonal Events and Activities

Jack’s Pumpkin Pop Up

An all-ages outdoor pop-up event with a corn maze, games, ax throwing, pumpkins, food, and drinks that takes place in September and October.

Visit a Pumpkin Patch

There are several pumpkin patches that are within easy driving distance from Chicago, making for a perfect day trip! Didier Farms hosts a pumpkinfest, Odyssey Fun Farm has zip-lines, a corn cannon, and a petting zoo, and Goebberts is a pumpkin patch and apple orchard with lots of activities including a corn maze, a haunted house, a train ride, and wagon rides.

Go Apple Picking

Apple Hollar, All Seasons Orchard, and Jonamac Orchard are all about an hour and a half from Chicago and offer apple picking and family-friendly activities.

Go on a Ghost Tour

Chicago Hauntings offers several ghost tours including a Devil in the White City tour and a Lincoln Park Ghost Hunt Tour.

Visit a Distillery

Check out Chicago’s new whiskey distillery, Judson & Moore. Located in Avondale, the distillery located in a former leather tannery beside the Chicago River is open for tours on Saturdays, or you can enjoy a drink at their bar on Thursdays – Saturdays.

Special Events

Chicago Gourmet

A weekend-long event showcasing some of Chicago’s best restaurants. Guests can try bites from dozens of restaurants, taste wines, and watch cooking demonstrations from well-known chefs. In 2022 the event will be held September 22-25.

Bike the Drive

On the morning of Bike the Drive, all lanes of traffic, in both directions, on Lake Shore Drive are closed so that cyclists can bike a 30-mile course. The event does require prior registration and tickets. Bike rentals are available. In 2022, the event will take place on September 4.

Chicago German American Oktoberfest

A Lincoln Square festival that takes place in September and includes live music, carnival games, performances from traditional dance groups, the Von Steuben Parade, and German food and beer. The 2022 dates for this event are September 9-11.

Revolution Brewing Oktoberfest

This beer-centric street festival that takes place on the last Friday and Saturday of September. The event features live music and Revolution Brewery’s seasonal Oktoberfest beer. In the past, metal bands played on Friday.


A collaboration between Begyle Brewing and Dovetail Brewery that celebrates Begyle’s birthday and allows Chicagoans to soak up the last of the warm weather. Special beers are tapped for the event and Oktoberfest-inspired food is served. The event benefits The Friendship Center. The event takes place in October, check Begyle’s Facebook page for details.

Riot Fest

A three-day rock music festival with five stages and over 80 bands that takes over Douglass Park on September 16-18, 2022. The lineup includes My Chemical Romance, Nine Inch Nails, Yellowcard, Yeah Yeah Yeahs, Ice Cube, Jimmy Eat World, and Alkaline Trio.

Buen Provecho! Taste of Pilsen

A September event held in conjunction with Mexican Independence Day that invites participants to taste bites from over 20 neighborhood restaurants, cafes, and bakeries. This event is different from other Chicago neighborhood food events because participants walk from restaurant to restaurant, instead of having the restaurants set up booths at a central location. 


Chicagohedge is an event when the sunrise and sunset happen to align with the skyline. It happens twice a year, usually around the spring and fall equinoxes. The fall equinox usually falls around September 22, making this event the perfect way to say farewell to summer and hello to fall.

Hyde Park Jazz Festival

A free event ($10 donation suggested) dedicated to supporting jazz music. The 2021 event showcased over two dozen bands. The next event is scheduled for September 24-25 2022.

Renegade Craft Fair

A massive market featuring art, crafts, clothing, and artisan goods that takes over Division Street in Wicker Park on September 10-11, 2022.

Chicago Artisan Market Ravenswood

The fall market featuring food, fashion, home goods, and art will take place November 26-27, 2022 at the Artifact Events Building in Ravenswood.

Open House Chicago

An annual event hosted by the Chicago Architecture Center each October. During this event significant architectural, historical, and cultural sites are open to the public for free – including some spaces that usually aren’t open to the public.

Día de los Muertos Xicágo

Hosted by the National Museum of Mexican Art at Harrison Park, this annual event takes place at the end of October and features ofrendas created by the community, art activities, and performances.

Thanksgiving Parade

An annual parade taking place on Thanksgiving morning from 8 am – 10 am. The parade route goes up State Street from Ida B. Wells Drive to Randolph Street.

West Town Art Walk

An event hosted by West Town galleries, home stores, and garden shops that celebrates local art with walking tours and special events. The 2022 dates are September 23-24.

Ravenswood Apple Fest

An October festival that welcomes autumn with live music, kid’s activities, farm stands, and a variety of apple-inspired food and drink. The event takes place on Lincoln Avenue between Lawrence and Wilson.

Ravenswood Wine Stroll

The Lincoln Square Ravenswood Chamber of Commerce hosts a wine strolls each fall. During this event, attendees get to taste wine at neighborhood shops. It is a popular event that tends to sell out – so purchase tickets in advance.

Lincoln Roscoe Beer Stroll

This event celebrates local breweries and businesses. Shop at locally owned businesses along Roscoe Street and Lincoln Avenue while tasting Chicago craft beer on Saturday October 22, 2022.

Halloween Events

Boo Palooza

An annual one-day event hosted by Mr. Dave’s Music at Wicker Park that combines live kid’s music, activities, and a costume parade.

Loyola Park Halloween Pet Parade

This event takes place from 9 am – 11 am on October 1, 2022, at Loyola Beach’s Painted Bench. There will be awards for Best Costume, Best Trick, Cutest, and Best in Show.