Things to Do in Chicago in Fall
· Updated · BootsnAll
I can't say it enough. Fall is my favorite time of year in Chicago. The sweltering days of summer have passed, and the freezing cold of winter has yet to arrive. There's a special feeling in the air as warm days give way to cool nights and the leaves turn red, yellow and orange. In my opinion, fall is one of the best times to be a tourist in Chicago, too. You can still spend plenty of time outside without shivering, and you don't have to fight off heat exhaustion or the summer crowds. And those bright leaves look even better from 94 floors up at 360 Chicago, the observation deck in the old John Hancock Center (now called 875 North Michigan Avenue). The Signature Room restaurant and its 96th-floor lounge, long a popular way to get that view with a drink in hand, closed in September 2023.
Here are some of my favorite fall activities in Chicago, plus what each month brings.
Fall, month by month
September still feels like summer. Highs average 75.5°F by the 1991-2020 normals at O'Hare. The Chicago Jazz Festival takes over Millennium Park and the Chicago Cultural Center on Labor Day weekend, Lincoln Square throws its German American Oktoberfest, and the beaches are still there to walk even after the lifeguards leave on Labor Day. See things to do in Chicago in September.
October cools to an average high of 62.7°F, and it's the busiest fall month. The Chicago Marathon runs on a Sunday in early to mid-October, Open House Chicago opens more than 200 buildings for a free weekend, the Chicago International Film Festival runs in the second half, and the Halloween season brings the Arts in the Dark parade downtown and the Haunted Halsted parade in Northalsted. See Chicago in October and things to do in Chicago in October.
November gets cold fast, with an average high of 48.4°F and the first snow possible. The holiday season kicks off the week before Thanksgiving. Christkindlmarket opens in Daley Plaza on the Friday before Thanksgiving, the Magnificent Mile Lights Festival follows the next day, and the Chicago Thanksgiving Parade goes down State Street on Thanksgiving morning. See things to do in Chicago in November.
Across all three months, Chicago Humanities (the old Chicago Humanities Festival) runs its fall season of talks and performances, and the city lists its own festival dates on the DCASE dates page. Our holidays and events page has the whole year.
Farmers markets
Green City Market is held year round, but the winter indoor market just doesn't compare with the outdoor one in Lincoln Park. It used to wrap up in October. These days the outdoor season runs into late November, both at the Lincoln Park market at 1817 N. Clark St. (Wednesdays and Saturdays, 7am to 1pm) and in the West Loop at 900 W. Monroe St. (Saturdays, 8am to 1pm), according to the market. Going on one of the last weekends is still a lovely, bittersweet thing. It's your last chance of the year to eat breakfast from the food stalls on a park bench, wander the rows sampling farm cheeses, and stock up on apples and squash straight from the farmers who grew them. More markets are on our farmers markets page.
Fall color, apples and pumpkins
The trees in Lincoln Park and along the lakefront are the easy option. For a full day of it, drive to The Morton Arboretum in Lisle, 1,700 acres of trees that Joy Morton of Morton Salt set aside in 1922. The arboretum says mid-to-late October is generally the peak, give or take a couple of weeks, and its Maple Collection is the place to be when it hits. Buy tickets online before you go.
Farther west, Kuipers Family Farm in Maple Park and Jonamac Orchard in Malta both do U-pick apples and pumpkins, and you'll need a car for either.
Sightseeing tours
There are dozens of sightseeing tours to choose from, like the Chicago Architecture Center's river cruise aboard the First Lady (the organization was the Chicago Architecture Foundation when this page was first written). Many sell out in summer. In the fall you can wait until the last minute to see what the weather does, and the cruise runs through November. It's 90 minutes and tickets start at $57. Bus tours and indoor tours are good rainy-day options.
>> more on sightseeing tours in Chicago and unusual tours in Chicago
Outdoor dining
Plenty of restaurants keep their patios and rooftop decks open into October, knowing there can still be quite a few nice days before fall really sets in. Call ahead once the weather turns, since a patio that's open on a 70-degree Tuesday can be closed on a windy Friday. There's nothing like lingering over a bottle of wine outside and soaking up the last warm days of the season. See the best outdoor dining spots in Chicago.
The Lincoln Park Zoo
I've always thought that the Lincoln Park Zoo is best visited in the spring and fall. The kids are back in school, so you can walk without tripping over a stroller, and the animals seem to have a bit more energy when the temperatures drop. It's free and open every day of the year. In late October the zoo throws an adults-only Halloween party, and ZooLights, its holiday light show, opens in late November. Check the zoo's calendar for dates.
Museums and a warm greenhouse
Fall brings its share of rainy days, which are the times to head indoors to one of Chicago's museums. Many are free on certain days (mostly for Illinois residents), and a few are always free, like the National Museum of Mexican Art in Pilsen, which puts up a Día de los Muertos exhibition every fall. When the gray gets to you, the Garfield Park Conservatory is the fix, a greenhouse full of palms and tropical plants on the West Side. It's free for Chicago residents and $10 for visiting adults, and reservations are strongly recommended.
>> more on Chicago museums and things to do on rainy days
Shopping
Bring an umbrella and dress for it (a raincoat and waterproof boots earn their suitcase space in a Chicago fall), and shopping turns into a good rainy-day plan. For high-end designers and the big chains, head to Michigan Avenue. If you'd rather dig through racks, the Brown Elephant resale shops, including one in Andersonville, raise money for Howard Brown Health, an LGBTQ+ health center. In Chicago, there's a shopping street for every taste and budget.
>> more on shopping in Chicago
Theater, comedy and music
Chicago has a thriving theater scene, and a cold autumn night is a good excuse to lose yourself in a show. Many companies open their new seasons in September and October. For the bigger, popular shows you'll need tickets in advance, but many smaller companies sell tickets on the day, often for less.
Bears, Blackhawks and Bulls
By October, all three teams are playing. The Bears play at Soldier Field from September, and the Blackhawks and Bulls start their seasons at the United Center in October. Dress warmer than you think for a Bears game in November. Soldier Field sits right on the lake.
For the weather and what to pack, see Chicago weather and what to wear in Chicago in fall.
Photos by: kern.justin, JanetandPhil