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Fall in Chicago
Photograph: Shutterstock

26 ways to still have an amazing fall in Chicago

Our guide to socially-distanced fall fun in and around the city.

By Emma Krupp

As far as seasons go, summertime in Chicago usually steals the spotlight (and okay, fair enough). But even so, you can't deny the appeal of fall in the city, when we get to trade hot weather for colorful leaves, crisp air, spiced beverages and plenty of spooky Halloween fun. Like everything else in 2020, fall in Chicago is going to look a little different this time around; nonetheless, you can still count on new, socially distanced versions of your favorite autumn pasttimes to make every bit of the fleeting season count. This list spotlights all the fall activities that we can safely partake in this year, from apple picking near Chicago to orange-and-red foliage spotting and beyond. Prefer to hang closer to home? Cozy up with some fall-friendly takeout and tune into the huge variety of at-home streaming content from Chicago venues and theaters. Here are the 26 ways you can still make the most of fall in Chicago. 

RECOMMENDED: Discover more of the best things to do in Chicago

How to still have an amazing fall in Chicago

Millennium Park
Photograph: Shutterstock

Check out the colorful display of fall foliage

Things to do

Nothing says autumn quite like a tree full of red, orange and yellow leaves—and luckily, we've got enough parks and foliage-filled outdoor areas to make tree spotting an especially easy autumn pastime. The first leaves start to go yellow in September, but wait until the first two weeks of October to catch Chicago's deciduous foliage in its full fiery splendor.

apple picking
Photograph: Shutterstock

Head to the countryside to pick apples

Things to do

Many of the best apple orchards in the Chicago area (and just over the border in Wisconsin and Indiana) are still open to the public with mask requirements, meaning you can spend an entire afternoon picking bushels of this fall-friendly fruit. Don't forget to grab a pint of cider and some cinnamon-dusted doughnuts on your way out!

Photograph: Mark Duffel

Visit a pumpkin patch


What's extra-convenient about apple orchards is that they're often home to pumpkin patches, too—so you can do some scouting for later in the season, when pumpkins and plump autumn gourds ripen on the vine. Stop by one of these farms for pumpkin picking, hay rides, corn mazes and tons of photo ops (just be sure to visit each spot's website ahead of your visit to review safety precautions, like timed reservations and capacity limits).

The Exorcist
Photograph: Courtesy Warner Bros

Get your screams in at the Music Box’s outdoor drive-in horror movie fest

News Movies

Traditionally, the Music Box of Horrors is a 24-hour horror movie marathon that takes place at the Southport theater, allowing attendees to take in an eclectic lineup of obscure, rarely screened films. This year's iteration takes the fest outside to Pilsen's Chi-Town Movies Drive-In for nightly screenings of grindhouse gems, spooky sequels and double features throughout the month of October.

Drive-in movie theater
Photograph: Shutterstock

Catch a drive-in flick on the big screen

Things to do

Not so into horror movies? Many of the drive-in movie theaters throughout the city and suburbs will remain open well into fall. Hop in a car, grab some comfy blankets and settle in for a screening (or double feature) of classic movies and recently released blockbusters.

Thimpson Strawberry Farm
Photograph: Courtesy Scott Thompson

Get lost in a golden sunflower field

Things to do

Sunflowers, the world's most cheerful flowers, have several blooming cycles that extend into mid- to late September, and you can visit a number of fields in the Chicago area to wander among their tall expanses. Be sure to check online to make sure the fields are open before visiting—and if you've missed their blooming period, many of these farms are also to other fun fall activities.

Tasha onstage at Hideout
Photograph: Sarah Larson

Stream a live show at the Hideout

News Music

With no safe way of allowing guests back into its relatively small performance space and no financial relief for music venues, the Hideout is doubling down on streaming programming. Teaming up with artist-friendly streaming platform NoonChorus, the Hideout is bringing all of its existing streaming content, plus new shows, to an online locale. On the NoonChorus platform, gaining access to a streaming show requires viewers to purchase a ticket. You can buy tickets à la carte, but hardcore Hideout fans might want to spring for a monthly subscription.


etta, jaclyn rivas, food, restaurant, wicker park, pizza
Photograph: Jaclyn Rivas

Order takeout or delivery from your favorite Chicago restaurants


Once the first October cold snap hits, cozying up on the couch with takeout will become all the more appealing—and what's more, it's a great way to safely support local businesses. We've put together a list of our go-to options here, ranging from takeout standbys to restaurants with brand new takeout menus. 

Pilot Project patio
Photograph: Courtesy Pilot Project

Sip craft brews in a beer garden


The city's regular roster of Oktoberfest celebrations are largely on hold this year, but you can recreate the pleasure of nursing a mighty stein of Pilsner (or any brew of your choice, really) at a number of beer gardens spread throughout Chicago. Don't forget to bring a jacket!

St. Louis
Photograph: Shutterstock

Skip town for a weekend


The Midwest is especially beautiful in autumn, so why not hit the road for a bit? With COVID-19 restrictions flattening normal travel plans, a road trip is an ideal way to beat wanderlust and see some new sights in the region, from bustling metropolises to quaint towns. Remember to keep an eye out for city travel orders and other public health office recommendations regarding COVID-19 before you visit.

Field Museum lobby
Photograph: Courtesy the Field Museum

See the sights in a newly re-opened museum


Many of Chicago's most iconic cultural institutions, like the Art Institute and Field Museum, have opened their doors with new safety guidelines in place. On the fence about whether you want to spend time in an enclosed space right now? Check out this guide to COVID-era safety measures to see how local museums are adapting (and if you're still uncomfortable, no worries: You can always explore some of Chicago's best museums from your couch). 

route 66, state street, illinois route 66, downtown, street sign, chicago, shutterstock
Photograph: Shutterstock

Go for a scenic drive

Things to do

Tour the city's sights in full autumn display on these gorgeous car trips, which weave through parks, downtown buildings and the lakefront. As always, be sure to bring a mask if you want to get out and explore. 

Photograph: Anjali Pinto

Have a slice of pie


Indulging in fall's favorite dessert is as easy as—well, pie—when you visit these local bakeries, which offer as much pecan, pumpkin, apple and otherwise spiced pie as you can muster eating. Order a slice for an afternoon treat or pick up an entire pie to bring home and share.

Finom Coffee
Photograph: Jaclyn Rivas

Get your pumpkin spice fix at a local coffee shop


Setting aside the occasionally polarizing PSL—which many of these spots have a homespun version of, if that's something you're into—fall is an ideal time to try out new coffee spots. We've rounded up some of our favorite cafes here: Pick up a steaming cup on your morning walk, step on some crunchy leaves and breathe in that crisp autumn air. 

Matthiessen State Park
Photograph: Shutterstock

Hit the trails at these nearby hiking spots

Things to do

There's arguably no better time to go for a long hike in the Chicago area than when the weather cools off and the leaves start to turn. Fortunately, you don't have to go far to find some pretty incredible trails for experiencing nature in autumn—some of the spots on this list are even within city limits. Remember to check ahead for closures and other safety requirements.

Courtesy Airbnb

Rent a cabin in the woods


Want to see some fall foliage up close? Book a weekend at these secluded Airbnb cabins located within a short drive of Cook County, where you can cozy up and relax among the trees. Some spots even provide outdoorsy tools—like fishing rods and kayaks—for built-in quiet recreation. 

elske patio
Photograph: Carolina Mariana Rodríguez

Bundle up and have a meal outside


We know what you're thinking: Why would anyone want to eat outside in Chicago once the weather turns? Putting aside the possibility of balmy fall days—which also swing around once in a while—it's worth noting that many Chicago restaurants will weather-proof their outdoor dining areas to prolong the possibility of alfresco meals. The city's even put out a call for proposals to extend outdoor dining through winter, so you can expect some form of patio seating throughout the season.

Skylanding, Yoko Ono
Photograph: Neal O'Bryan

Explore the city's abundance of public art

Things to do

You can view works by the likes of Picasso, Calder and Hebru Brantley on Chicago's plazas and street corners, if only you know where to look. From sculptures to murals and beyond, these tremendous public artworks are always free to visit.

Wiz Khalifa
Photograph: Shutterstock

Try Wiz Khalifa's new stoner-friendly, delivery-only restaurant

News Eating

Recreational weed has been legal in Illinois since the beginning of this year. Come October, though, Chicago stoners will be able to quelch the munchies with the help of HotBox by Wiz, Wiz Khalifa's new delivery-only restaurant that plans to serve up some of the rapper-weed entrepreneur's favorite dishes to eat while blazed. 

Garfield Park Conservatory
Photograph: Brian Kinyon Photography

See the flowers that inspired Monet at Garfield Park Conservatory's new outdoor exhibit

News Art

In conjunction with the "Monet and Chicago" exhibition at the Art Institute, the Garfield Park Conservatory is hosting a concurrent outdoor exhibit featuring all the flowers—asters, dahlias, nasturtiums and roses—that have been featured in Monet's paintings. Make a timed reservation and bring a mask; the flower-filled exhibit will remain open as long as weather permits. 

Central Perk
Photograph: Marc Berry

Tour a “Friends”-themed interactive exhibit

News City Life

You won't be able to binge-watch Friends on Netflix this fall—instead, head to this experiential pop-up that's coming to Michigan Avenue beginning October 1, where you can tour exhibits related to the iconic sitcom's history. Book ahead for a timed, socially-distanced session in the pop-up.

Chicago Archiecture Center boat tour
Photograph: Courtesy Chicago Architecture Foundation

Cruise down Lake Michigan or the Chicago River

Things to do Walks and tours

Many of Chicago's best boat tours reopened this summer at 50 percent capacity, which means you can once again cruise down the Chicago River or Lake Michigan to learn about history and architecture while you take in city sights—even on a chilly fall day. Bring a warm jacket and a mask and prepare to see Chicago from a new point of view.

harold washington, harold washington library, library, chicago library, CPL, loop, downtown, the loop, shutterstock
Photograph: Shutterstock

Check out books from home with an electronic Chicago Public Library card

News City Life

Most Chicago Public Library locations have reopened, but if you prefer to minimize your time in public places, you can still check out tons of e-books online from the comfort of your home. Head to CPL's website to browse the available selection of digital books (and brace yourself for a bit of a wait for newer titles).

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