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Fall in Chicago
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26 ways to still have an amazing fall in Chicago

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

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Written by
Emma Krupp
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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

  • 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.

  • 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!

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  • Kids

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).

  • Movies
  • 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.

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  • 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.

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  • Music
  • 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.

 

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  • Travel

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.

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  • Museums

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). 

  • 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. 

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  • Restaurants

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.

  • Restaurants
  • Coffee shops

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. 

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  • 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.

  • Travel

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. 

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  • Bars

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.

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  • Art
  • 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. 

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  • Things to do
  • 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.

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More things to do this fall in Chicago

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