Fall in Chicago is a great time to visit. There are plenty of sunny days still left to enjoy. Heading out of summer, the weather can range between 4-23–degrees between September and November. So you’ll want to pack a sweater for September and something much warmer and waterproof by November. As the crowds are heading home, it’s one of the best times to explore the city and to join in the fun and festivities. And of course, the perfect time to hop aboard an open-top bus tour.

If you plan to be in Chicago in fall, we’ve rounded up our top picks of things to do:

Take a look around

During this shoulder season, you’ll find yourself enjoying fall in October with the locals as opposed to the tourists. So do take a minute to appreciate the calm and just look around. Take in the autumnal colour palette and head to nature’s beautiful spots to see it at its best. Stroll along the Riverwalk and check out the art and fountains along the way. Pack a picnic (and a jacket) and head to Grant Park for a lazy afternoon. Or if you’re feeling a little more energetic, hike through the city along the 606. Twice the length of New York’s High Line, this former railroad has been converted into a great space for hiking or cycling, with iconic sights in full view en route.

For Grant Park:
The Big Loop – Red Route, Stop: Hilton Chicago & Grant Park

Get Festive

Fall in Chicago is festival season, with themes covering food, culture and music, to name a few. If you’re a foodie you won’t want to miss Chicago Gourmet at the end of September. Fine wine, gourmet food, and over 150 talented chefs. When you get thirsty head to Oktoberfest, a traditional German beer festival that also lines up live bands and family events. And at the end of November, the Holiday Flower Show opens. The Lincoln Park Conservatory is transformed into a Winter Wonderland filled with poinsettias, trees and twinkling lights.


In mid-November, the city starts to warm up for the holiday season, a clear sign it’s fall in Chicago. And Christkindlmarket kicks off the festivities. Taking inspiration from the 16th century Christmas market in Germany, it is now the largest of its kind in the United States with over a million guests flocking to them across the country. It’s free to enter and browse the many stalls offering hand-blown ornaments, crafts, toys for all ages, traditional food and drink. A great place to do your Christmas shopping.

The Big Loop – Red Route, Stop: The Loop & State St.

Celebrate Thanksgiving

If you happen to be in Chicago in November, you’ll get to witness the Thanksgiving Parade and all the celebrations around this important holiday. A Chicago tradition since 1934, creative floats, gigantic balloon and marching bands parade up State Street. You’ll see incredible performances and even a visit from Santa Claus! The energy is high and the vibe is excitable. Make sure you show up early to bag a good spot. 

Movies in the park

At the beginning of fall in Chicago, you can still catch a movie in the park. Hosted in parks across the city, watch the sky light up as recent films as well as old classics are screened. Millennium Park is a particularly popular destination, playing movies in the Jay Pritzker Pavilion every Tuesday night. Bring a blanket, some tasty supplies, something to drink, and you’ll be set for a lovely evening.

For Millennium Park:
The Big Loop – Red Route, Stop: Maggie Daley Park

So there you have our list of must-do activities during fall in Chicago. A time when summer starts to fade and the city gears up for lots of festive fun. And on a sunny day, you can grab a top-deck seat on a Big Bus tour, and we’ll take you to see the best sights and attractions Chicago is famous for. For more inspiration on how to fill the rest of your time in the Windy City, check out our guide to the Top 10 Things to do in Chicago.