Chicago Fall Guide: Weather, What to Take & Top Things to Do

As a lifelong Chicagoan, I’ve spent many fall days uncovering the best ways to enjoy the city, and in this guide, I’m sharing all the essentials.

You’ll find out what kind of weather to expect, what to pack (including my go-to layers), and my top picks for what to see and do in the city from September through November.

Whether you’re here for cozy cafes, seasonal events, or just a walk under golden leaves, here’s everything you need to make the most of a Chicago fall.

A Chicago Fall: What to Expect

When planning a fall trip to Chicago, it’s helpful to know which are the official autumn months, and what it’s like to be here during the post-summer period. 

What month is fall in Chicago?

September, October and November are the fall months in Chicago. 

Is Chicago good to visit in the fall? 

A Chicago fall is wonderful, with colorful leaves and many events to experience. During the day, temperatures are mild and pleasant, though it can be cool during the night, early morning, and evening hours. 

Overall, it’s warmer in fall than during spring, with temperatures and hours of daylight gradually dropping between September and November.  

Daily highs range from around 73°F (23°C) in September to about 50°F (10°C) during November. It’s colder at night, but usually well above freezing. During fall in Chicago, you can expect around five days of rain per month on average. 

Best Things to Do in Fall in Chicago

This is my handpicked list of the best things to do and places to go when visiting Chicago in September, October or November. 

1. Open House Chicago

One thing I love about Chicago is the impressive architecture. You can’t miss it, as it’ll be all around you. But once a year, there’s a citywide event that highlights architectural gems across the city even more.

Open House Chicago is an annual event that occurs in mid-October. It showcases the city’s stunning architecture by offering free insider tours of more than 170 buildings in more than 20 neighborhoods.

The sites range from private homes to historic structures and modern skyscrapers. It’s also a perfect solo thing to do in Chicago. The last time I participated, I explored the interior of the Elks Monument in the Lincoln Park neighborhood.

I also visited a church and a residential building usually closed to general public. It’s a great way to get an in depth look at different parts of the city.  

2. Sample seasonal drinks at Chicago cafes and bars

Chicago’s local and best coffee shops and bars offer an appealing array of seasonal drinks to sample during fall. From a caffeinated pick-me-up to cocktail hour, local places always try to outdo one another with their autumnal creations. 

During the day, get a giant mug of hot chocolate topped with a giant homemade marshmallow at Mindy’s in Wicker Park.

After dark, try Billy Sunday or the Market Bar at Time Out Market for flavorsome concoctions, or cozy up at The Violet Hour to experience cozy fall feels. 

3. Pick-your-own at a pumpkin patch

There are plenty of places to pick your own pumpkin around Chicago. But if a spot within the city would be more convenient, look out for Jack’s Pumpkin Pop-Up. It’s held every September at Goose Island in downtown. 

I was lucky enough to go the very first year the pop-up patch began, and it was so fun! There are plenty of photo opps, some incredibly artistic carved pumpkins, a corn maze, seasonal treats and drinks. This was both kid and adult-friendly, I know my niece would love it!

4. Chicago Ghosts & Haunted History Tour

Despite its lively energy, Chicago has a darkside as well. Immerse yourself in a spooky, scary walking tour where you’ll learn about the city’s haunted past (and present!) led by an expert local guide. 

👻 Click to reserve your spot on the tour

5. Day of the Dead

Why not celebrate Día De Los Muertos in Chicago? The historic, character-packed Pilsen neighborhood is where the annual fall race, Carrera de los Muertos, takes place at the start of November. It’s held at Dvorak Park, with a lively festival following the race. 

The National Museum of Mexican Art, also in Pilsen, also hosts an annual Day of the Dead exhibition in the main gallery, between mid-September and mid-November. 

Personally, I believe this museum should be required viewing anyway. It’s fast to go through and fascinating. The Pilsen neighborhood is also such a gem, so if you need a Halloween excuse to get out there then take advantage of it.

6. See spectacular fall foliage 

Chicago’s parks and gardens put on a stunning display of fall colors every year. The best time to see it is between the middle of October and the beginning of November. 

Head to Lincoln Park, the Botanic Gardens, the Lakefront Trail, or any neighborhood park to see the finest foliage during mid-to-late fall. 

7. Enjoy seasonal events

Halloween events are held all over Chicago during fall. Options include Spooky Zoo at Lincoln Park Zoo, and Brookfield Zoo’s Boo at the Zoo.

There’s also the Northalsted Halloween Parade and Arts in the Dark on State Street in The Loop, both of which take place after nightfall. 

If you won’t be here for Halloween, pick between a variety of seasonal food festivals. From Chicago Gourmet or Lincoln Square Apple Fest to Chicago Beer Festival, Lincoln Park Wine Festival, and Oktoberfest, there are plenty of options to whet your appetite.

8. Find your way through a corn maze

A popular local activity in Illinois during fall is to visit a corn maze. There are lots to choose from close to Chicago, including the biggest corn maze in the world at Richardson Adventure Farm.

This sprawling place offers almost 10 miles of trails in total, made up of four smaller mazes. 

9. Harvest season at the farmers markets

While shopping at a Chicago farmers market is a pleasure at any time of year, fall is the perfect time to pick up the best seasonal produce. 

Local favorites include the Green City Farmers Market in Lincoln Park, as well as those at Glenwood, Logan Square, Wicker Park and Lincoln Square. 

10. Head outdoors

Chicago in fall provides ideal conditions for lovers of outdoor activities. Whether you want to take a leisurely stroll through a city park or bike, hike, or run along by the lake, autumn is ideal for exploring the great outdoors.

Temperatures are comfortable, the city is beautiful and people are still buzzing from a post-summer high (you know, before we all go into winter hibernation!).

That plus the fact that I get to celebrate my fall birthday in Chicago make this one of my favorite times of year to enjoy the city.

What to Pack when Visiting Chicago in the Fall

For a fall trip to Chicago, paying attention to weatherproofing and layering is the best approach. Packing pants and jeans is a good idea, plus some short and long-sleeved tops. 

Sweaters

Take a couple of hoodies or sweaters to layer over your outfits when it’s chilly – such as during early mornings and late evenings. 

Weatherproof jacket

On top of your t-shirt or sweater you can also layer a lightweight or fleece-lined rain jacket, which will protect you from wet and windy weather.

Accessories 

According to what the weather brings, add sunglasses or a scarf, hat, and gloves to help make conditions more comfortable. 

Comfortable shoes

Exploring Chicago typically involves a lot of walking, so take at least one pair of comfortable, sturdy shoes.

Final Thoughts on Enjoying a Chicago Fall

I hope this guide has helped you decide whether a fall trip to Chicago could be for you.

With the absence of summer crowds and lower winter temperatures, September, October, or November can be the ideal time to visit the Windy City. To set yourself up for a successful visit any time of year, don’t miss my top Chicago travel tips.