Explore Fun Fall Activities in Chicago

Coffee BreakSeptember 8, 2022

Chicagoland is wonderful all year-round, but there’s something about fall in Chicago that is uniquely special. Whether you want to ‘Ooh’ and ‘Ahh’ over the bright fall colors, pick out your own pumpkin for a sweet or scary jack-o’-lantern, celebrate Halloween with fun costumes, or face the frights at a local haunted house, here are some fun ways to thoroughly enjoy your fall evenings and weekends.

While you’re taking in all the season has to offer, don’t forget to use your GLCU debit card for your paid activities! Whenever you use your GLCU debit card, you’ll automatically be entered to win our exciting fall giveaway, started for the back-to-school season! For this giveaway, GLCU will cover $150 in debit card expenses for ten winners, with one winning member chosen each week until September 19, 2022.

As always, you’ll earn free debit rewards and a competitively high APY on your free checking account balance, just for swiping your GLCU debit card on everyday purchases. Be sure to get your GLCU debit card by visiting your local GLCU branch, or order one by calling us at 800-982-7850.

Benefit from these perks by using your GLCU debit card on one (or more!) of the exciting events going on this fall near you.

Fall-themed tours

Self-guided and Walking Tours

One of the best ways to get out and enjoy the cool breeze and enjoy the Fall colors in Chicago is to take a self-guided or guided walking tour of various neighborhoods or maybe a specialty tour like an evening Ghost Tour to learn about Chicago's Haunting History.

If walking isn’t your thing, there are other options:

Here are some top places to see fall colors in and around Chicago:

  • Lincoln Park, particularly the area around North Pond and South Pond
  • Jackson Park and the gorgeous Garden of the Phoenix
  • Morton Arboretum just a short train ride away

Explore more: Read the full fall colors guide to Chicagoland.

Open House Chicago

Once a year, from October 1-31, the city opens up to the public for Open House Chicago to explore the incredible architecture from the inside. Go behind-the-scenes to more than 250 buildings in Chicago during this free public festival, from skyscrapers to private residences.

Ghost Tours

Chicago has a spooky history and you can have some fun exploring the past. Check out the Chicago Ghost Tour Pub Crawl by Nightly Spirits and feel the hair on the back of your neck raise as you discover what lurks behind the shadows. Keen to explore more? Find the full guide to haunted Chicago tours here. Or create your own DIY walking tour with this list of Chicago’s most haunted places.

Festivals and Parades

Fall brings an exciting blend of food and drink events to Chicago. Check out these crowd-pleasing choices:

Oktoberfest

This German tradition continues for another year in the Windy City. Grab some cold beer, bratwurst, and pretzels as you enjoy the authentic German bands and culture. For a true Oktoberfest experience, check out the German-American Oktoberfest in September.

Chicago Gourmet 

This three-day event, taking place from September 23 to September 25, hosts a German beer festival, a burger competition, and an elevated tasting experience.

While you’re out, be sure to stop for some Craft Brews at Lincoln Park Zoo – this event lets you sip local beer in a historic setting.

Halloween Festivities

Chicago celebrates Halloween with its own innovative style, with artistic evening spectacles. Attend the Arts in the Dark Halloween Parade on State Street before you wander down the Congress Hotel for the Haunted Halloween Ball. 

Trick-or-treating

Trick-or-treating with kids on Halloween is a must! Try a different neighborhood this year, as some communities have a whole host of activities for kids.

Night of a 1,000 Jack-o-lanterns at the Chicago Botanic Gardens is a must-do for the whole family. They have an entire calendar of spooky, educational fun.

Ravenswood Manor: check out this historic district to admire the houses as well as collect candy. In the past, it's also won the reputation of the best neighborhood to trick-or-treat in.

Lincoln Park Zoo hosts the very popular annual Spooky Zoo, an event that hosts a number of free activities for kids of all ages. 

Northalsted Halloween Parade in North Halsted (aka Boystown)

Boo! at the Zoo at Brookfield Zoo

You can also celebrate Halloween in the parks!

Interested in a more culturally themed event after October comes to a close? Attend the Día de los Muertos: Love Never Dies Ball on November 5, at the National Museum of Mexican Art and enjoy culinary treats from some of Chicago’s best restaurants, sip on delicious adult beverages, and dance the night away to one of Chicago’s best DJs.

Explore more: Check out this guide to Halloween events and activities for more.

Special thanks to Free Tours By Foot : https://freetoursbyfoot.com/chicago-in-the-fall/  and Choose Chicago: https://www.choosechicago.com.

Concerts and Theatre

There are plenty of great shows happening in Chicago this fall. Going to a concert is a great way to cap off an evening after spending the day touring the glittering city of broad shoulders.

Some big names coming to Chicago this fall:

September:

October:

As for live theatre in the fall in Chicago—can’t beat the dynamic theatre scene! Catch pre-Broadway runs, world premieres, classic favorites, cutting-edge shows, and more.

Explore more: Find theatre events and shows all over Chicago.

Family-Friendly Fall Activities

Pop Ups, Patches, and Picking

Nothing says fall quite like pumpkin patches, corn mazes, and apple picking. Check out some local pop-ups and nearby farms for hayrides for the kids and apple cider for the adults.

Pop-Ups

Local Farms

Explore more: Fill your basket with apples and other seasonal produce at your nearest Chicago farmers market.

Festivals and Parades

The Lincoln Park Zoo is hosting Fall Fest, a celebration of fall running from Sept.27-October 27, Friday-Sundays. The event is free and guests can enjoy viewing the animals, taking their picture with a giant pumpkin, and delicious snacks. While a lot of activities are free, there are ticketed events as well, like a corn maze, inflatable obstacle course, and more!

More popular fall festivals:

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