Things to Do in Chicago in Fall

I can’t say it enough. Fall is my favorite time of year in Chicago. The sweltering days of summer have passed; the freezing cold temperatures of winter have yet to arrive. There’s a special feeling in the air as warm days give way to cool nights, and hues of red, yellow and orange color the leaves. In my opinion, fall is one of  the best times to be a tourist in Chicago as well. You can still spend plenty of time outside without shivering, but you don’t have to worry about battling heat exhaustion (or the other hordes of tourists either). Prices on flights to Chicago are lower, and those brightly colored leaves I just mentioned – yeah, they look pretty spectacular from the 96th floor of the John Hancock building. Here are some of my favorite fall activities in Chicago.

Farmer’s Markets

Green City Market is held year round, but the winter indoor market just doesn’t compare with the one held outdoors in Lincoln Park from late May to October. The market closes this month, and it’s a lovely bittersweet feeling to attend one of the last weekends, a last chance to grab a crepe or elk burger and picnic in the park, a last chance to wander from stall to stall sampling farm-fresh cheeses, and a last chance to support local farmers while stocking up on the best produce, meat, and breads.

Sightseeing tours
There are dozens of sightseeing tours – like the Chicago Architecture Foundation River cruise or the Chicago Film Tour – to choose from, but many are completely packed (and even sell out) in the summer. During the fall months you can wait until the last minute (to see how the weather will be) to book without fear of missing out, and some of the tours that take place entirely indoors or within a bus, are perfect activities for rainy days.

>> more on sightseeing tours in Chicago

Outdoor dining

Many restaurants keep their patios and rooftop decks open for dining and drinking until the end of October, knowing that there can still be quite a few nice days before fall really sets in.  There’s nothing like lingering over a bottle of wine on an outdoor patio, soaking up the last warm days of the season.

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 actually walk without tripping over a stroller, and it seems like the animals have a bit more energy when the temperatures drop.


Of course, with fall comes a few rainy days, which are the times you should head indoors to check out some of Chicago’s best museums.  Many of these museums are free or offer free days throughout the year, and no matter what type of art, history, or science you are interested in, you’ll find a museum that caters to it.

>> more on Chicago museums


Bring an umbrella and dress accordingly (a raincoat and a pair of waterproof wellie boots are vital during Chicago’s fall season), and you’ll find that shopping can be an excellent rainy-day activity. If you’re looking for high end designers (along with some more accessible chains), head to Michigan Avenue. Prefer the thrift stores? Check out the Lakeview ‘hood around Broadway. 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 theatre scene, and cold autumn nights are perfect for losing yourself in a show inside a dark theatre. For some of the bigger, more popular shows, you’ll need to buy tickets in advance, but many of the smaller shows and performances spaces sell tickets the day of the show, often at a discount.

>> more on theater in Chicago

Photos by: kern.justin, JanetandPhil