Autumn in Chicago mesmerizes us with its crisp breezes and holiday countdown. The city and its surrounding suburbs are bustling with pop-ups and markets, apple picking, pumpkin carving, and the beginning of numerous holiday celebrations. Check out our list of essential summer-to-fall activities, delectable foods, and captivating performances with this TOP Five Things to Do in Chicago This Fall!

Halloween in the City

Halloween in Chicago is a unique holiday, celebrated unlike any other in the city. This year, do you have a fantastic costume planned? The Annual Upside Down Halloween Parade, which kicks off Halloweek 2023, is a festive and enchanting Halloween event that encourages Chicago children and their families to become the parade by donning costumes and joining the procession down Russell Drive, which is lined with trees. The Grand Finale of Chicago's Halloweek 2023, the Arts in the Dark parade, celebrates Halloween as the artist's holiday and has been dubbed Chicago's Neighborhood Parade because it brings together cultural organizations and artists.

Image Courtesy of Chicago Thanksgiving Parade

Each Halloween, Halsted becomes a bit eerie! Join on October 31 for the annual Haunted Halsted Halloween Parade. Registration and the parade begin at Halsted and Belmont. The End of the Parade is at Halsted and Brompton.

The Annual Arts in the Dark is a mystical evening procession that brings together celebrated Chicago institutions such as the Art Institute of Chicago. It is a spectacular production that enchants 50,000 spectators with unique displays, spectacle puppets, and creative performances – all against the backdrop of State Street's historic architecture. Halloweek is a renowned annual event that attracts a large number of Chicagoans. Anyone in costume is invited to attend!

There are artistic evening spectacles, glowing pumpkin displays, spooky excursions of haunted houses, family-friendly festivals, and more in Chicago's Halloween celebrations. Check out some of the most anticipated events of this year:

Arts at Night on State Street within the Loop
Spooky Zoo and Howl-o-ween at the Lincoln Park Zoo
Boo! at the Zoo at Brookfield Zoo Seasonal Shows
Explore a unique pumpkin field

There is no autumn without a visit to a pumpkin farm. And you don't even have to leave the Chicago metropolitan area. Our seasonal pumpkin patches consist of an extravagant pop-up, an artist-driven nocturnal display, and a family-friendly zoo event.

Jack's Pumpkin Pop-up is touted as Chicago's largest fall festival. Jack's takes over Goose Island with a variety of seasonal activities, such as fortune tellers, a corn maze, food trucks, photo ops, and over 10,000 pumpkins.
This family-friendly festival continues through October at the Lincoln Park Zoo. The free event features an adorable pumpkin field, ideal for autumn photographs.
During this eerie after-dark event, pumpkins carved by artists will illuminate the Chicago Botanic Garden.

Shows for the Season

There are numerous Broadway shows that perfectly complement the eerie atmosphere of the autumn season. Nothing beats the excitement of live theater. The curtain will rise this autumn on Chicago's thriving theater scene, from our stunning downtown venues to our cozy neighborhood stores. There are numerous exciting Broadway in Chicago productions, world premieres, classic favorites, hit musicals, and family-friendly performances. Be sure to enjoy the pleasant autumn weather during the day before heading to the theater in the evening!

Observe the Autumn Leaves

Embracing the enchanting autumn foliage in Chicago is a delightful celebration of autumn's chilly, crisp air. Immerse yourself in the vibrant colors and rustling leaves by taking a leisurely promenade through some of the city's parks. From the picturesque landscapes of Lincoln Park and the natural beauty of Humboldt Park to the iconic appeal of Millennium Park and the tranquil environs of the Morton Arboretum, each location offers its own distinctive tapestry of seasonal change. As the leaves change, these cherished green spaces transform into tranquil havens, providing the ideal escape from the bustling metropolis to experience the essence of autumn. Don't overlook the expansive lagoons and wildflowers in Humboldt Park, as well as the Night of 1,000 Jack-O-Lanterns at the Chicago Botanic Garden!

Image Courtesy of ***Northalsted Halloween Parade***

The Season in the City

Chicago's holiday season is always magnificent and full of enchanting traditions. If you're in the city during Thanksgiving, don't miss the Chicago Thanksgiving Parade, which features enormous balloons, intricate vehicles, and festive performances. It is a cherished annual event that signals the start of holiday festivities.

Autumn Culinary Celebrations

The autumn brings a variety of exciting food and drink festivals to Chicago, including Chicago Gourmet, one of the city's signature culinary events. These upcoming events celebrating the city's cuisine, beer, and wine scenes will satisfy foodies' cravings:

The Chicago Gourmet event features a German beer festival, a burger competition, and a refined tasting experience.
The fall harvest is celebrated at the Lincoln Square Apple Fest with apple pie, apple cider, and other autumnal delights.
The Chicago Beer Festival showcases seasonal beverages from over 60 local breweries within the renowned Field Museum.
Guests of the Lincoln Park Wine Festival can sample wines while strolling through an open-air market featuring sommeliers, culinary samples, and live music.
The Cider and Ale Festival honors seasonal beverages at the picturesque Morton Arboretum just outside of Chicago.
At this prestigious competition, the Festival of Wood and Barrel-Aged Beers offers samples of the rarest wood and barrel-aged beers.

The crisp air and impending holiday excitement of Chicago's autumn capture us every year! Pop-ups and markets are everywhere! Apple picking, pumpkin carving, and the beginning of many holiday activities fill the city and suburbs with activity. As the season changes from summer to fall, have fun with this list of must-dos, must-eats, and must-see shows for the TOP Five Things to do in Chicago This Fall.

TOP FIVE THINGS TO DO IN CHICAGO THIS FALL