Chicago is perfect in the fall. Summer’s heat and humidity have gone away, and they haven’t quite been replaced by winter’s harsh chill. The parks are gorgeous, since all of the leaves are changing color and carpeting the ground below. Wind speeds range from moderate to impressive, depending on how close you are to the lakefront, and everyone is decked out in Chicago Bears and Blackhawk’s sports fan gear.

There’s no better time of year to spend your days taking in all that Chicago has to offer– here are some fall activities to get both, longtime locals and visitors started:

View From Above

Top Fall Activities in Chicago - View from Above

If you’re looking to get a look at the fall foliage, do it from over 1,300 feet in the air! Willis Tower’s SkyDeck is an enclosed, all-glass balcony that goes four feet off the edge of the building’s 103rd floor. There’s no better place to take a look at the city, as well as the changing colors on the trees throughout Chicago.

Too nervous to step out onto SkyDeck’s glass floor? You can still get a great view from the top of the tower.

Sampling Refreshments

Top Fall Activities in Chicago - Sampling Refreshments

There are lots of breweries in Chicago, and fall is when they roll out some of their seasonal beers. Consider going on a brewery tour to get a feel for one particular brand, or hit up different bars through town to try some of the different drinks on tap.

If you’re not sure where to start, check out the Chicago Brew Bus. This bus takes you on a tour of local breweries, giving you the chance to try beers from multiple locations in one event. This is the perfect choice for someone new to Chicago’s beer scene, or who simply wants to try a wide variety of beers.

Apple Picking

Top Fall Activities in Chicago - Apple Picking

Although you won’t find apple trees in Millennium Park, there are plenty of orchards an hour or so outside of town. The Heinz Orchard is only 37 miles away– you can pick a variety of apples there, including McIntosh, Jonathan, and Golden Delicious.

They don’t have hay rides or other fall activities, but they’re the perfect place to get right down to the main event– pulling fruit off of trees. After all, that’s all anyone really wants out of life.


Top Fall Activities in Chicago - Shopping

Head down the Magnificent Mile to find all the hottest fashions and stock up for next season. The shops along this stretch of Michigan Avenue have options for every style and budget.

If you’re not tied to trends, late autumn is the perfect time of year to pick up fall clothes. All of the season’s best will be on discount, which means you can spend less and be well-prepared for next year.

Getting Lost

Top Fall Activities in Chicago - Getting Lost

One of the coolest things you can do during the fall is lose yourself in a corn maze. Luckily for Chicagoans, there’s a 4-acre corn maze about an hour and a half drive from the city. Dollinger Farms boasts the enormous maze, which has a different theme each year and promises hours of fun.

Once you’re through the maze, you can head over to the farm’s petting zoo. There you can feed and pet goats, sheep, pigs and rabbits. Don’t forget to check out the gift shop on the way out– you can buy toys, gifts, local honey, and the farm’s habanero pickles.

Zoo Trips


The Lincoln Park Zoo is open all year round, but there’s something special about visiting in the fall. In the first few months of the season, the mild weather makes it perfect for spending a few hours outdoors. Later in autumn, the zoo features its ZooLights show, a holiday-themed light display that’s sure to impress.


Top Fall Activities in Chicago - Whirlyball

When the weather gets cold, head inside to try your hand at Chicago’s most ridiculous sport. Whirlyball is a cross between basketball, lacrosse, and hockey that’s played in bumper cars.

I’ll just let that sink in.

Here’s a more detailed description: You use hand-held scoops to move a whiffle ball down the court and into the goal. You travel up and down the court in bumper cars that have been modified for speed and agility. You’re probably not going to be good at Whirlyball– few are– but you’ll have a great time being terrible at it alongside friends or strangers.

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