Leaves are falling, temps are slowly dropping, and PSLs are back on the menu. That’s all we need to know to declare it officially fall in Chicago. We know you’re just as excited as we are for the best season of the year and can’t wait to check everything off your list. So let’s get right to it.
Consider this your complete guide for fall activities near you in Chicago.
Do Fall Stuff
Some of the best fall activities in Chicago take place in the Midwestern fields of the suburbs. If your fall bucket list consists of visiting a pumpkin patch, apple orchard, or corn maze, we recommend visiting one of these highly rated, picturesque locations. And make sure not to miss out on any Oktoberfest celebrations.
- Bengtson Farms – Homer Glen, IL
- Kroll’s Fall Harvest Farm – Waukegan, IL
- Goebbert’s Farm and Garden Center – South Barrington, IL
- Curtis Orchard & Pumpkin Patch – Champaign, IL
- Kuiper’s Family Farm – Maple Park, IL
- Jonamac Apple Orchard – Malta, IL
- Richardson Farm – Featuring world’s largest corn maze in Spring Grove, IL
- Pumpkin Patch at Horner Park – October 5 | 10 am – 2 pm
- Pumpkin Patch at Ada Park – October 6 | 12 pm – 4 pm
- Pumpkin Patch at Hale – October 12 | 11 am – 3 pm
- Pumpkinpalooza at Skinner – October 12 | 11 am – 3 pm
- Mini Pumpkin Patch at Bell – October 13 | 12 pm – 3 pm
- Pumpkin Patch at Sheridan – October 19 | 10 am – 1 pm
- Pumpkin Patch at Humboldt – October 19 | 10 am – 1 pm
- Pumpkin Patch at Portage Park – October 19 | 10 am – 2 pm
- Pumpkin Patch at Rainey – October 19 | 11 am – 3 pm
- Jack’s Pumpkin Pop-up at Goose Island – October 3 – November 3
Eat Food & Drink Beer
After a summer of painstaking efforts to stay fit, one of the most exciting parts about fall is having the chance to eat hearty comfort foods in front of a warm, burning fire and layer up so no one knows how much weight you’re gaining during hibernation season. There are a lot of fall activities near you in Chicago at cozy spots in the city where you can treat yourself to a delicious meal in front of an inviting fireplace.
- The Dawson
- Hubbard Inn
- North Pond
- Owen & Engine
- The Violet Hour
- Le Bar at Sofitel
- Tortoise Supper Club
- Uncommon Ground
While you’re out, here are some fall beers from Chicago brewers to look for on menus that’ll pair great with your meal.
- Revolution – Oktoberfest
- Off Color – Waddle Oktoberfest
- Solemn Oath – Oktoberface
- 3 Floyds – Munsterfest
- Goose Island – Oktoberfest
- Two Brothers – Atom Smasher
- Half Acre – Lead Feather Black Ale
You can also hit up an Oktoberfest event, which of course, screams food and beer during fall in Chicago. Check out our Oktoberfest guide to see the best ones taking place throughout the city.
Go For a Run
One of our favorite fall activities in Chicago is running in brisk fall temperatures and breaking a cool, comfortable sweat. Plus, you get to burn off all the calories you’ll put on from eating the comfort foods and drinking the beer we recommended above. Take a scenic run on the lakefront or through one of the city’s many beautiful parks. Want to join a group? Check out these Chicago runs.
- Run Mag Mile – September 7 @ Grant Park
- Chicago Marathon – October 13 @ Grant Park
- Country Sole – October 19 @ Montrose Harbor
- Hot Chocolate 5k/15k – November 3 @ Grant Park
- Chicago Turkey Trot – November 28 @ Lincoln Park
- Grant Park Turkey Trot – November 30 @ Grant Park
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Fall in Chicago means only one thing for sports fanatics. FOOTBALL. It’s Bears season and time to cheer them on with family and friends. Most Chicagoans fall bucket lists consist of hosting a tailgate or visiting some of the best sports bars in town to catch the game. If college football is more your speed, check out the best places to catch Big Ten games.
If you want to go extra hard with an event that takes tailgating to the next level, the Bacon & Beer Classic is a glorious fall celebration that’s inviting you to sport your favorite jersey and put your game face on to eat all the bacon and beer you can imagine at Soldier Field.
Coffee has a way of warming your soul on a cold day… but, like, also your body, because that’s kind of important, too. If you’re looking for a relaxing fall activity in Chicago, grab your favorite roast, a pumpkin spice latte, or a hot chocolate from a cafe in your neighborhood. Or check out our list of best iced coffee if that’s more your thing.
Either way, here’s a few to start.
- Osmium Coffee Bar – Lakeview
- Big Shoulders Coffee – West Town
- Filter Cafe – Wicker Park
- Jupiter Outpost Coffee – West Loop
- Gaslight Coffee Roasters – Logan Square
Take In Some Culture
Autumn is a season that makes people feel inspired. If it gets too chilly outside, appreciating art, culture, and education is the perfect indoor fall activity near you in Chicago to celebrate the season. Here are some awesome events coming up this fall, and you can always hit up museum free days when they’re available.
Duh, obviously fall means Halloween time. You can’t have one without the other! This can be a very overwhelming holiday, especially in a city like Chicago where there’s so much going on. Stay tuned for our upcoming guide to everything happening for Halloween in Chicago. Every. Single. Thing.
In the meantime, check out these witchy places to get into the spirit.
- Bucket O’ Blood Books & Records
- Shadow Emporium Apothecary & Shoppe
- Occult Bookstore
- Sideshow Gallery
5 Activities to Add to Your Official Chicago Fall Bucket List
There are plenty of ways to have fun during the fall season in the city of Chicago. We recommend adding these items to your official bucket list.
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