Chicago Fall Fun: Top Things to Do in the Windy City in Autumn

Camryn Cutinello Avatar
Pumpkin carved with the word "Chicago"
Chicago has no shortage of fun fall activities that people of all ages will enjoy. Photo credit: Lincoln Park Zoo.

Fall colors, pumpkin patches, haunted houses, great architecture and a Day of the Dead celebration are just a few of the fun things to do in Chicago in the fall. It’s one of the best times of the year to be in the Windy City. The summer humidity is gone and the fresh breeze off of Lake Michigan makes it a good time to bundle up in a sweater and walk along the lakefront or try one of these fun fall activities.

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A line of jack-o-lanterns created by professional artists on display at Chicago Botanic Garden.
A line of jack-o-lanterns created by professional artists is available for viewing during the Night of 1000 Jack-O-Lanterns at the Chicago Botanic Garden. Photo credit: Chicago Botanic Garden.

Chicago Botanic Garden

For visitors looking to spend some time outside and see the fall foliage, the Chicago Botanic Garden in north suburban Glencoe hosts a variety of fall-themed nature walks. Held throughout the season, these walks give guests time to experience nature and view the changing colors the Chicago area has to offer.

The gardens also host a Fall Festival and Bulb Sale on Oct. 4-6, which is full of live music, a hay-bale maze and a harvest market. For those planning ahead for their garden, bulbs from more than 200 varieties of flowers will be available for purchase.

Later in October, the gardens will be taken over by pumpkins for the Night of 1000 Jack-O-Lanterns. These aren’t your neighborhood kids’ pumpkin carvings. These jack-o-lanterns are carved by professional artists. The 2024 dates are October 16 – 20 & 23 – 27.

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Happy Jack, Goebbert’s mascot
Happy Jack, Goebbert’s mascot, watches over the farm and festival. Photo credit: Goebbert’s Pumpkin Patch and Apple Orchard

Goebbert’s Pumpkin Patch and Apple Orchard

With apple picking, a corn maze and a pumpkin-eating dinosaur, Goebbert’s Pumpkin Patch is a great way to spend a fall day.

With locations in Pingree Grove and South Barrington, there’s also a kid-friendly haunted house, hayrides and that fall must-have: apple cider donuts. Kids can also enjoy chicken and pig races, and even get the chance to ride a pony or a camel.

The Fall Fest is open daily through Halloween. Also be sure to check out the Harvest Market for produce from local farms.

Dia de los Muertos exhibit at the National Museum of Mexican Art in Chicago
School children learn about the Day of the Dead celebration in Mexican culture. Photo credit: National Museum of Mexican Art

National Museum of Mexican Art

Located in Pilsen, the National Museum of Mexican Art offers the opportunity to see art that spans more than 3,600 years. The museum’s annual Dia de los Muertos: Love Never Dies exhibit opens on Sept. 20 and runs through early November.

SheBuysTravel Tip: Parking can be a challenge in Pilsen. Leave the car and take the Pink Line L train from the Loop. It’s the best deal in town for just $2.25 a ride!

Oktoberfest in Chicago
The beer garden and one of the two stages at Chicago’s Oktoberfest. Photo credit: Special Events Management.

Chicago Oktoberfest

Oktoberfest has become one of the biggest fall events hosted in Chicago. The three-day festival boasts live music, traditional German dancers and, of course, cold brews.

The festival is not just for beer lovers! The Kinderfest section of the festival features family-friendly games and kids’ activities. When you get hungry, there is plenty of hand-made brats and other German foods available for sale.

Taking place on the grounds of one of Chicago’s oldest churches, St Alphonsus, 1429 W. Wellington Ave., the event features German bands, dancers and even some sing-alongs. Event dates for 2024 are Sept. 27-29. Admission is a suggested donation of $10.

Woman and man with a wagon walks past Fall Fest sign at Lincoln Park Zoo in Chicago.
Lincoln Park Zoo hosts a Fall Fest for people of all ages to see the animals and enjoy the fall spirit. Photo credit: Lincoln Park Zoo.

Lincoln Park Zoo

Lincoln Park Zoo, one of the last free zoos in the country, celebrates the fall season with a Fall Fest. The free event takes place Fridays-Sundays, September 27–October 27.

Walk through the harvest maze and the pumpkin walk, go on the kid-friendly rides and see the zoo from atop the Ferris wheel. The event also boasts live music, professional pumpkin carvers and, of course, the zoo animals.

Ghost story lovers can also take part in a Haunted History Tour every Tuesday and Wednesday of October and learn about some of the history behind Lincoln Park.

The zoo also will offer trick-or-treating on Oct. 19, beginning at 10am and lasting until the treats are gone. An adults-only Howl-O-Ween event is set for 6:30-10pm Oct. 24. The paid ticketed event is a fundraiser for the zoo.

Chicago Ghost Tours

For spooky fall fun, try Chicago Ghost Tours from Free Tours by Foot. The adults-only walking tours explore the haunted history of the city and the greater Chicagoland area.

The tours begin at the haunted Congress Hotel, and then visit some of Chicago’s other haunted spots. Learn about serial killers H.H. Holmes and John Wayne Gacy, and take a journey through the history of Chicago’s Red Light District and Death Alley.

Tours take place 3-4 times a week and begin at 6 p.m. It’s a name-your-own-price tour, so guests can decide afterward what it was worth. The tour is spooky — don’t bring the kids!

People buying apples at Apple Fest in Chicago's Lincoln neighborhood
So, Many. Apples! All on sale at Apple Fest in Chicago in the fall. Photo credit: Lincoln Square Ravenswood Chamber of Commerce.

Lincoln Square Ravenswood Apple Fest

The annual Lincoln Square Ravenswood Apple Fest features food from local restaurants, tables with goods from local businesses and plenty of activities and entertainment.

Mouth-watering food highlights include: dessert apple tacos, apple cinnamon rolls, apple empanadas and the American classic, apple pie. The fest also features booths from local farms, specialty food vendors and local small businesses.

The 2024 event takes place Oct. 5 and 6 and also features live music and a Kids Zone.

Gorgeous fall colors on a tree at Morton Arboretum near Chicago.
The Morton Arboretum, located in west suburban Lisle, has walking paths, hiking trails and gorgeous fall colors. Photo credit: The Morton Arboretum

Morton Arboretum

The Morton Arboretum is beautiful any time of the year. but it’s breathtaking in the fall. This is a spot to take a contemplative walk among the trees. Or attend of the many special events planned for fall. There’s the annual bulb sale that starts on Sept. 20 and runs through October. On Oct. 5, it’s the Cider and Ale Festival. The weekend of Oct. 11-13 is the time to see the amazing Glass Pumpkin Patch You can watch glass-blowing demonstrations, see their beautiful creations on display and buy one to take home.

On Oct. 26, the Arboretum will host its Fall Color 5K Run and Walk. Register online in advance of race day.

Wil Color exhibit at the Field Museum in Chicago in the fall
The Wild Color exhibit at the Field Museum explores the science of nature’s colors. Photo credit: Field Museum.

Chicago’s Museums

The city has no shortage of museums to keep adults and kids entertained, while also learning something. Here are the fall highlights.

  • The Field Museum will host “Boo with Sue,” a family-friendly after-hours exploration of the creepy crawlers and spooky specimens in the museum’s collection. Costumes encouraged!
  • The Griffin Museum of Science and Industry will host BOO Fest on Oct. 24.
  • The Art Institute of Chicago will host “Dia de los Muertos: Cel;ebrating LIfe” at 2pm on Nov. 1. Available in both English and Spanish, the event will highlight works of art throughout the museum.
Docent leading a Chicago architectural tour
Learn about historic buildings surrounding the Chicago River during the Chicago Architecture Center’s walking tour. Photo credit: The Chicago Architecture Center.

Chicago Architecture Center

Beyond the usual walking and boat tours offered by the Chicago Architecture Center, the center hosts Open House Chicago every October. One of the largest events of its kind in the world, the 2024 dates are October 19 and 20.

The free public festival offers self-guided history and architecture tours throughout Chicago,including behind-the-scenes access to architecturally, historically and culturally significant sites across the city.

Camryn Cutinello graduated from Columbia College Chicago in May with her bachelor’s in journalism, and is currently working on her master’s degree at the University of Illinois Springfield in Public Affairs Reporting. She loves to write about anything and everything, especially Chicago city life, politics and sports. When Camryn isn’t writing, you can find her out running, hiking or spending time with friends and family.
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