top of page
  • Writer's pictureLFaits

4 Ways to Make the Most of Chicago this Fall

It is officially my favorite season: Fall! Growing up in New England, I have always loved the crisp air, comfy sweaters, and apple picking that come along with Autumn. Here in Chicago, however, things are done a little differently. Here are some of the must-sees this season in the Windy City:


Get your hands on your finest lederhosen, polish up your biggest stein, and dive in to a smorgasbord of schnitzel, sausage, & sauerkraut. St. Alphonsus is probably the most well-known place to celebrate Oktoberfest (September 29-October 1,) but there are so many more places to embrace German culture. Festivals are going on all over the city, so jump on Google and search them out!

If  full-on festivals aren’t your speed, you can still grab some great food & drinks. Some of the most famous locations include Chicago Brauhaus, The Berghoff Restaurant, and The Radler.

2. Fall flavors, the Chicago way

We all know that Fall hasn’t truly arrived until apple cider and pumpkin spice make their way into every drink and pastry around town. This fall, do apples and pumpkin right with these Chicago institutions. I’ve searched high and low to find the absolute best Chicago has to offer, and these are it!

If pumpkin spice is your thing, try the pumpkin patch latte at Ipsento Coffee on 2035 N. Western Ave. You’re going to want to pair that latte with a sweet fall treat, as well. Have no fear! I have you covered!

Stan’s Donuts is home to some of Chicago’s best donuts, so it should be of no surprise that they making some of the best Apple Cider donuts this fall. Grab them at any one of the many locations around Chicago.

If pumpkin pie is more your speed, don’t fret! Check out the Hoosier Mama Pie Company in Ukrainian Village for all the best pies including seasonal favorites.

3. Da BEARS & Cubbies

There’s nothing quite like a football game in the Fall. Soldier Field is one of the best arenas to experience it in. Make sure to grab your favorite sunglasses and practice your Super Bowl Shuffle before you see the Chicago Bears!

If football isn’t your speed, be sure to check out the defending World Champion Chicago Cubs at Wrigley Field. The over 100-year-old stadium is one of the most beautiful around. As the October playoffs quickly approach, there’s no better time to visit! Make sure to toss back any opponent home run balls that might come your way though. Who knows? You just might make the team after showing off your impressive arm!

4. Go for a run!

Do you like running? Neither do I. How about watching other people run? Well then, the Chicago Marathon is for you! As one of the most prestigious races in America, make sure to follow this event on October 8.

26.2 isn’t quite your speed? How about something a bit shorter… and spookier?

Check out the Pumpkins in the Park 5k on October 21 in Lincoln Park. Throw on your favorite running gear (or costume if that’s your style) and race toward Halloween!

So, grab your favorite flannel & your best wool knit beanie because Fall is HERE. Go out and see all Chicago has to offer.

Comment below with your favorite seasonal Chicago happenings!

bottom of page