UrbanMatter’s Complete Guide to All Things Fall in Chicago

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. 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.


Do Fall Stuff

fall in chicago

Easily the best part of fall is heading out into Midwestern fields to pick your share of autumn’s bounty. Plan your day to visit a pumpkin patch, apple orchard, or corn maze at one of these highly rated, picturesque locations. And make sure not to miss out on any Oktoberfest celebrations.



  • Pumpkin Patch at Portage Park
  • Pumpkin Patch at Ada Park
  • Pumpkin Patch at Horner Park
  • Pumpkin Patch at Veteran’s Memorial


Eat Food & Drink Beer

fall in chicago
Photo Credit: Zagat

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. Spend an evening at one of these cozy spots in the city where you can treat yourself to a delicious meal in front of an inviting fireplace.

While you’re out, here are some fall beers from Chicago brewers to look for on menus that’ll pair great with your meal.

You can also hit up an Oktoberfest event, which of course, screams food and beer. Check out our Oktoberfest guide to see the best ones taking place throughout the city.


Go For a Run

fall in chicago

There’s nothing like 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.



fall in chicago
Photo Credit: Just Make Pictures

Who’s ready for some football? It’s Bears season and time to cheer them on with family and friends. If you aren’t hosting a party in your yard or living room, we know 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.


Drink Coffee

fall in chicago

Coffee has a way of warming your soul on a cold day… but, like, also your body, because that’s kind of important, too. So 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.


Take In Some Culture

fall in chicago
Photo Credit: Pbase

Autumn is a season that makes people feel inspired. If it gets too chilly outside, appreciating art, culture, and education is the perfect indoor activity. Here are some awesome events coming up this fall, and you can always hit up museum free days when they’re available.


Get Spooky

fall in chicago

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.


What are your favorite fall activities in the city? Tell us about them below!


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