There’s nothing quite like fall in Chicago, honestly, it’s a great time of the year to be in the Windy City.
The crisp air, changing leaves, and the city’s mix of outdoor adventures and cozy indoor escapes make it the perfect season.
With so many things to do, it can feel overwhelming—but don’t worry. I’ve rounded up the best fall activities in and around Chicago, from wandering corn mazes and catching outdoor concerts to finding your next favorite fall read or exploring free museum days.
This guide is designed to help you make the most of the season.
Best Fall Activities in Chicago
Where to See Fall Colors in and Around Chicago
Cool air and changing leaves are reason enough to explore outdoors. Here’s how to experience fall foliage in the city and nearby areas:
In the City
- Chicago Riverwalk: Stroll along the water and admire the colorful trees before the walk closes for the season.
- Lakefront Trail: Bike or walk the trail during mid-October for peak color.
- Neighborhood Parks:Humboldt Park, Lincoln Park, and Jackson Park are the best for a quiet fall stroll without leaving the city.
Day Trips Near Chicago
- Morton Arboretum (Lisle): Stunning tree displays and trail walks for all skill levels.
- Starved Rock State Park (Utica): Hike waterfalls and canyons while surrounded by fall foliage.
- Matthiessen State Park: A quieter option to Starved Rock, with waterfalls, canyons, and brilliant fall foliage, minus the big crowds.
Celebrate Fall Festivals Across the City
Chicago doesn’t just do fall — it celebrates it. Each neighborhood offers a diverse range of festivals, music, art, and food experiences.
Downtown / Millennium Park
- Chicago Jazz Festival (August 28 – 31, 2025) – Free performances by world-class jazz artists across Millennium Park and the Chicago Cultural Center.
- Chicago Gourmet (September 25 – 28,2025) – A foodie must-do with celebrity chefs, tastings, and wine experiences in one of the city’s most iconic locations. Pro Tip: Buy tickets early for limited tasting sessions.
South Side
- African Festival of the Arts (August 31 – September 1, 2025) – A four-day celebration of Black art, music, and culture, including crafts, food, and performances.
- 79th Street Renaissance Festival (September 6, 2025) – Family-friendly block party featuring local food, games, and live entertainment. Free admission.
- Hyde Park Jazz Festival (September 27 – 28, 2025) – Free, intimate jazz performances across Hyde Park’s cultural landmarks, including Rockefeller Chapel.
North Side
- Lincoln Square Apple Fest (October 4-5, 2025) – Classic fall vibes with apple cider, local vendors, and live music along Lincoln Avenue. Pro Tip: Check the schedule for cooking demonstrations and apple pie contests.
Citywide / Other Neighborhoods
- Chicago Humanities Festival (September – November) – Conversations, lectures, and performances with leading thinkers, authors, and artists across multiple venues.
- Open House Chicago (October 18 – 19, 2025) – One weekend only: explore historic homes, architectural gems, and usually off-limits buildings. Pro Tip: Reserve spots for popular locations in advance.
- Chicago Fashion Week® 2025 (October 9 – 19): A week-long celebration bringing together fashion designers, models, and creatives to showcase the city’s growing influence in global style.
- The 61st Chicago International Film Festival 2025: A city-wide celebration of global cinema featuring dramas, documentaries, comedies, and programs highlighting Illinois filmmakers, with in-person screenings across multiple theaters and venues.
Outdoor Adventures & Activities
Fall is a great time to get outside. Here are neighborhood and suburb-based adventures for all ages:
Pumpkin Patches & Corn Mazes
- County Line Orchard (Hobart, IN): Apple picking, pumpkin patch, and seasonal treats.
- Kuipers Farm: Early-season apples, flowers, and seasonal drinks.
- Sonny Acres Farm: Classic pumpkin patch fun and hayrides.
Watch an Outdoor Movie
- Catch your favorite film at the Rooftop Cinema Club at the Emily Hotel with cozy blankets and stunning city views.
Halloween & Haunted Tours
- 13th Floor Haunted House and Statesville Haunted Prison: Chicago’s biggest haunted attractions with movie-quality scares.
- Explore Chicago’s spooky side with Lincoln Park and South Side ghost tours, the Medieval Torture Museum, and the Chicago Crime & Mob Bus Tour.
Haute Tip:Dress in layers for fluctuating fall temperatures and wear comfortable shoes for walking and hiking.
Food & Drink Experiences This Fall
Chicago’s culinary scene shines in autumn with pop-ups, seasonal menus, and neighborhood favorites:
- Sip Seasonal Drinks at Local Cafes: You can enjoy Pumpkin spice lattes, apple cider, and fall-inspired pastries at neighborhood favorites like Goddess & the Baker, Cadinho, and Afro Joe’s.
- Pop-Up Bars & Speakeasies: Hidden gems like Blind Barber, The Sparrow, and popular Jack Pumpkin serve seasonal cocktails in intimate, cozy settings.
Arts, Culture, & Cozy Indoor Experiences
When it’s chilly, Chicago’s indoor activities will keep you warm. Here are some of the best ways to enjoy fall indoors:
- Visit Chicago Museums on Free Days: Field Museum, Shedd Aquarium, and Museum of Science & Industry all offer free admission days, perfect for exploring culture without breaking the bank.
- Browse Neighborhood Bookstores: Women & Children First or Da Book Joint make fall reading adventures extra cozy.
- Try a Seasonal Cooking or Baking Class: Learn new recipes with pumpkin, apple, and other fall ingredients from spaces like Bettie’s Chicago.
Chicago’s Top 7 Fall Buckelist Activities for 2025
- See fall foliage at the Morton Arboretum or Starved Rock.
- Attend at least one fall festival per month — music, food, or arts-focused.
- Pick apples or pumpkins at a nearby farm.
- Try a seasonal pop-up dining experience or cocktail bar.
- Take a scenic drive or neighborhood walk to enjoy autumn colors.
- Visit a museum or gallery on a crisp fall day.
- Cozy up indoors with a fall-inspired dinner, a good book, or your favorite local cafe.
