While Chicago may be famous for its euphoric summertimes, fall still has plenty to offer before the gauntlet of pain better known as “winter” arrives. As a Chicagoan of 14 years and born-and-raised Midwesterner, I don’t think fall gets nearly as much love as it deserves: The seasonal foods are richer, the calendar of things to do is superior, and who doesn’t love cozying up to watch a scary movie while eating candy by the handful? I’ll kindly step off my soapbox and offer you 15 more reasons why fall in Chicago is an unimpeachable delight.
1. Leaf peeping season is in full swing.
According to Explore Fall, fall colors will paint Chicago’s foliage throughout October, so now is prime time to start planning your leaf peeping expeditions. Head to some of the more well-known Chicago parks and gardens to see towering oaks and fiery red Japanese maples, or take a contemplative stroll through a cemetery to watch yellow weeping willows drape over a leaf-filled pond. If you’re itching to take a quick day trip from Chicago, you’ll find several suburban conservatories and arboretums on our list of the best spots to admire fall foliage.
2. Drinks taste better in a beer garden (that’s just science).
Sometimes the best beer pairing isn’t burgers and fries—it’s a cool breeze and sunshine dappling your face. Luckily for us Chicagoans, there are plenty of beer gardens—most of which are dog-friendly—for alfresco boozing and schmoozing. We even compiled a full list of Chicago’s best beer gardens just for you.
3. Strolling through a cemetery is seasonally on-brand.
If you’re angling to spend an afternoon soaking in nature's quiet, look no further than Chicago’s cemeteries. These contemplative environs serve as the final resting spots of countless famous Chicagoans—so many, in fact, that you could spend hours getting lost among the stately tombstones and crypts studding their manicured grounds, which rival even the most scenic Chicago parks. Unsurprisingly, many of these spots also number among the most haunted places in Chicago, so try not get too scared when you visit the most beautiful cemeteries in Chicago.
4. It’s finally apple picking season.
Few things are as glorious as the bragging rights that come with bringing home a basket of apples you picked with your bare hands. If you’re not much of an outdoors person, pick up a bag of pre-picked apples and a box of cinnamon donuts from an orchard and feel like a hero. Whichever path you choose, we’ve done some extensive research and found 14 delightful apple orchards for all of your seasonal fruit-related needs.
5. Club shows take precedent over music festivals.
Sure, sweating and stage-hopping at one of Chicago’s many outdoor music festivals is its own type of fun, but fall brings with it special shows at venerable Chicago venues like Metro, Empty Bottle, Outset and more. This year, the Empty Bottle is celebrating its 33 ⅓rd anniversary with a slew of solid underplays (The Pains of Being Pure at Heart; Cindy Lee), while Metro is hosting some indie favorites (Purity Ring; Minus the Bear) and ‘80s throwback acts (Andy Bell of Erasure).
6. You can carve a jack-o’-lantern from a pumpkin you picked yourself.
Sure, rolling up to Jewel to pluck a dusty ol’ pumpkin from their parking lot bin is sufficient, but that’s forfeiting the thrill of bobbing and weaving through a vine-covered pumpkin patch, piping hot cider in hand. Bask in the bounty of Chicagoland’s many pumpkin patches and pick up a locally grown gourd for your carving pleasure. Most pumpkin patches offer fresh baked goods, hay rides and more, so you easily can—and should—make a day of it.
7. There’s no shortage of drive-in movies.
It’s no secret that Chicagoans love their outdoor movies—from Movies in the Parks to Music Box Theatre’s Garden Movies series. If you're looking to take your alfresco moviegoing to the next level, might we recommend the humble drive-in movie? One of the most satisfying autumnal activities is loading up a car with as many snacks as your dashboard can hold, setting up a tailgate-style spread with friends or getting cozy for an old-school date at one of the best drive-in theaters near Chicago. Just make sure those windshields are spotless.
8. It’s prime time to hike.
Looking for an outdoorsy experience that’s a bit more adventurous than rambling through your neighborhood park? Cross state lines to visit the gorgeous Indiana Dunes along Lake Michigan, explore the ruins of a steel mill in Joliet or tackle the sprawling 30-mile Ice Age Trail at Kettle Moraine State Forest in Wisconsin. If you’re yearning for a quick escape from the city, put on your best boots and hit the trails at some of the best places for hiking near Chicago.
9. Candy is technically a food group for the month of October.
As the recovering child of a health-nut household, autumn feels like sweet revenge with candy overflowing from grocery aisles and the city’s best confectionaries. Whether you’re looking for silky caramels or cloud-like marshmallows for the most decadent s’mores on this side of the Mississippi there’s plenty of ways to satisfy that sweet tooth at the best candy and chocolate shops in Chicago.
10. Night of 1,000 Jack-o’-Lanterns returns.
On of the best times to visit the Chicago Botanic Garden is in the midst of its annual ghoulish makeover. Night of 1,000 Jack-o’-Lanterns corrals more than 1,000 LED-lit pumpkins—some weighing up to 150 pounds—and stages them along the garden’s pathway. Just over half of those pumpkins will be intricately carved with themes including tributes to Chicago sports teams, beloved pets and much more. Seasonal snacks and drinks are available for purchase, in case all that wandering makes you hungry.
11. Street festivals galore.
From Oktoberfest celebrations and makers’ markets to Halloween parades, street festivals pack Chicagoans’ calendars all season long. Some personal favorites include Sundays on State, Arts in the Dark and Begyle and Dovetail Brewing’s joint birthday party Oktoberfestiversary. To make sure you never miss a Chicago street festival, bookmark our Things to Do section.
12. Chicago International Film Festival dominates your favorite movie theaters.
Some of the latest and greatest movies to hit the festival circuit arrive in the Midwest during the Chicago International Film Festival, which typically presents a lineup of around 100 dramas, documentaries, comedies and foreign films, plus several short film programs. Don’t miss the opening night screening of One Golden Summer, a documentary about Chicago’s Jackie Robinson West Little League—the first all-Black team to win the Little League U.S. Baseball Championship. Learn about other programming on the Chicago International Film Festival website.
13. Museums transform into haunted houses.
Chicago’s museums take Halloween seriously: The Shedd Aquarium transforms into a haunted house for the 21-plus crowd, Chicago Shakespeare Theater is bringing a stage adaption of Paranormal Activity to its stage, the Field Museum returns with its spooky after-hours event and much more.
14. We can all be ghost hunters, even just for a day.
If you’ve ever wanted to have a real paranormal encounter, Chicago has plenty of destinations where you can cosplay as a ghost hunter. I’m not just talking historic buildings with reported hauntings—music venues, cemeteries and hotels throughout Chicago all have ghost stories surrounding them, too. If you’re ready for activities of the supernatural persuasion, check out our list of the 26 most haunted places in Chicago.
15. Open House Chicago is back.
Want to peep past the doors of iconic Chicago buildings like the Chicago Board of Trade Building or Walt Disney's childhood home? You'll have your chance to get a free, behind-the-scenes look when the Chicago Architecture Center’s annual festival Open House Chicago returns, opening up more than 170 architectural wonders across the city for free tours. This year marks the 15th anniversary of the always-free public festival—with the anniversary comes new locations, a transit plan and more.