Best Fall Things To Do in Chicago: Festivals, Food, and Seasonal Fun

Chicago in the fall is pure magic. The crisp air off Lake Michigan, the colorful leaves scattered across city parks, and the cozy glow of neighborhood cafés make autumn one of the best times to explore the Windy City.

In my opinion Chicago has something for everyone. I have been living in Chicago since 2004, and from my personal experience, whether you’re a foodie chasing seasonal flavors, a culture lover excited for festivals, or someone simply looking for outdoor adventures before winter sets in, Chicago has something for everyone.

Here’s the list of the best fall things to do in Chicago that covers different kinds of festivals, food, fun activities, tours, and hotel stays to make your trip unforgettable.

1. Fall Festivals That Celebrate Chicago’s Spirit

Chicago Gourmet

Every year in September month Millennium Park transforms into a foodie’s paradise during Chicago Gourmet festival. It is a culinary festival that highlights the city’s top chefs and mixologists. You will have great time enjoying gourmet tastings, wine pairings, and live cooking demos. I feel that it’s the perfect chance to savor the creativity of Chicago’s food scene while enjoying the crisp autumn air.

📌 Pro tip: If you’re traveling in for the weekend the check out hotels near Millennium Park on Expedia.com for easy access to all the festival action.

Oktoberfest Chicago

No fall season is complete in Chicago without Oktoberfest, yes because Chicago does it big. Neighborhoods like Lincoln Square and Lakeview host lively celebrations featuring German beer, bratwurst, live music, and traditional dancing. Grab a stein, join the polka, and feel like you’ve been transported to Munich.

Open House Chicago

If you’re curious about Chicago’s stunning architecture then consider to take advantage of Open House Chicago in October. The city opens doors to hundreds of unique buildings, yes these sites include historic theaters, ornate churches, rooftop gardens, and private clubs that are usually closed to the public. It’s free, inspiring, and perfect for a fall weekend of exploring.

Want a guided take on the city’s history and skyline? Book an architecture tour on Viator to pair with the event and learn from local experts.

Apple Fest in Lincoln Square

For many of Chicagoans, nothing screams fall like apples, Yes, like I mentioned Lincoln Square’s Apple Fest has you covered. From hot apple cider and fresh apple pie to apple butter and caramel apples, this festival celebrates the season’s sweetest harvest. Add in live music and family-friendly activities, and you’ve got the perfect neighborhood outing.

2. Seasonal Food & Drinks You Can’t Miss

Cozy Up with Chicago Pizza

Deep-dish pizza is always a favorite not all the time, but I feel that in fall it feels especially comforting. Stop by Lou Malnati’s, Pequod’s, or Giordano’s and dig into a piping hot slice while the temperatures dip outside. Pair it with a local craft beer for the ultimate Chicago fall meal.

All Chicago style deep dish pizza places are good, but among all Lou Malnati’s is my favorite place to enjoy the slice.

📌 Tip for visitors: Staying near River North or the Loop makes it easy to explore famous pizzerias. I recommend to compare options on Expedia for central hotels close to all the food spots.

Farmer’s Markets in Full Swing

Fall brings a bounty of squash, apples, and root vegetables to Chicago’s local farmer’s markets. I recommend to check out Green City Market in Lincoln Park or the Logan Square Farmers Market to pick up seasonal produce, baked goods, and locally made treats. It’s a great way to support small businesses while tasting the flavors of autumn.

3. Fun Fall Activities for Everyone

Explore Chicago’s Parks and Trails

I have been living in Chicago since 2004, and every year since then have seen the beautiful fall foliage around the city. Especially Chicago’s parks turn into colorful works of art during fall. Lincoln Park offers beautiful views of the skyline framed by autumn leaves, while the Chicago Botanic Garden showcases seasonal plant displays. The 606 Trail, an elevated path through neighborhoods, is another great spot for a fall walk or bike ride.

For visitors: stay near Lincoln Park with boutique hotel options on Expedia so you’re just steps from fall foliage and local dining.

Take a Chicago River Architecture Cruise

Architecture cruises on the Chicago River are popular all year, but fall adds a special touch. You will have great time enjoying Chicago downtown views with trees adding colorful fall colors. You can check my list of popular Chicago boat tours.

Imagine floating down the river with golden leaves lining the banks and the city’s iconic buildings towering above. Many cruises even serve warm drinks so you can sip cider while learning about the city’s rich history. There are many boat companies offering Architecture cruise such as shoreline sightseeing, Chicago line cruises and many similar.

👉 Book a Chicago River Architecture Cruise on Viator to experience it with live commentary and unbeatable views.

Halloween in Chicago

Many of us know that Chicago goes all-out for Halloween. From haunted houses like 13th Floor Chicago to neighborhood trick-or-treating events, there’s spooky fun for everyone. Families can head to Lincoln Park Zoo’s “Spooky Zoo,” while adults can join bar crawls or haunted history walking tours.

👻 Don’t miss a Chicago Haunted Tour from Viator for ghost stories, creepy landmarks, and a fun seasonal adventure.

4. Cultural Events & Arts in Autumn

Chicago International Film Festival

If you are one of film buffs then you will love the Chicago International Film Festival, held every October. It showcases independent films, international features, and premieres from award-winning directors. Screenings are held across the city, making it a cultural highlight of the season.

📌 For convenience, book hotels in the River North or Loop area on Expedia so you’re close to festival theaters and nightlife.

Symphony and Theater Season

Fall marks the start of Chicago’s theater and symphony season. The Chicago Symphony Orchestra returns with world-class performances, while theaters like the Steppenwolf and Goodman Theatre debut new plays. For a lighter evening, catch a comedy show at The Second City.

5. Classic Fall Experiences Around Chicago

Pumpkin Patches and Corn Mazes

I highly recommend to take a short drive from the city to family-friendly pumpkin patches and corn mazes. Places like Goebbert’s Pumpkin Patch and Bengtson’s Pumpkin Farm offer hayrides, petting zoos, and seasonal treats like kettle corn and apple cider donuts. In my opinion it is perfect things to do for a family with young kids during one of the weekends in fall season.

🚗 Many tours and transport packages to farms and suburban fall festivals can be found on Viator—ideal if you don’t want to rent a car.

Day Trips for Fall Foliage

This is my one of the favorite things to do in Chicago during fall season. I highly recommend to consider to take a mini road trip, explore the fall foliage in nearby areas like Starved Rock State Park or the Morton Arboretum. Both locations offer breathtaking autumn views, hiking trails, and picnic spots.

📌 Stay in downtown Chicago via Expedia and plan foliage tours or day trips with pickup options directly through Viator.

So, friends from my personal experience as a Chicagoan, I feel that Chicago in the fall is a city alive with color, flavor, and energy. From world-class festivals and foodie experiences to cozy cafés, sports games, and cultural events, there’s something for everyone. Whether you’re a local planning your weekends or a visitor discovering the Windy City, fall offers endless opportunities to celebrate the season.

👉 Ready to plan your trip? Book your Chicago tours with Viator and compare the best Chicago hotel deals on Expedia today to make the most of your autumn adventure.