28 of the Best Fall Activities in Chicago

There is nothing quite like fall in the Midwest, especially in a place like Chicago. The city welcomes the change of season, with a hearty list of things to do. From apple picking in a nearby suburb to making a fresh batch of your favorite soup from scratch, this guide is perfect for enjoying the fall season indoors and outside.

Note: While we encourage you to enjoy one or all of these activities, we recommend keeping yourself and others safe by practicing safe social distancing rules and regulations.


Fall Activities

1. Pick apples at a local orchard.

2. Hike winding trails during a family outing.

3. Savor a delicious bowl of ramen

Ramen // Image by Taylor Justin

4. Make your way through a complex corn maze.

5. Select the best pumpkins at a pumpkin patch.

6. Cook a stew, chili, or soup from scratch.

7. Take a scenic drive to watch the leaves change.

8. Lounge in a cozy cabin.

9. Volunteer for a grassroots organization.

10. Go antique shopping in a swanky neighborhood.

11. Bake an apple pie from scratch—or any other fall fruit.

12. Go stargazing.

13. Make it a frightful night and visit a haunted house.

14. Mix a cozy fall cocktail during date night.

15. Go horseback riding through the countryside.

Horeseback riding in Michigan // Image by Taylor Justin

16. Snuggle up with a good book.

17. Tune in to an outdoor concert.

18. Host a costume party.

19. Take a weekend trip to a small town or cool city near you.

20. Quench your thirst with beer from a local brewery.

21. Become one with nature by camping or “glamping” in the great outdoors.

22. Attend a seasonal festival.

23. Watch your favorite scary movie at a drive-in theater.

24. Embrace fandom and attend a football game.

25. Visit a cool art gallery.

Frida Kahlo at the Cleve Carney Timeless Exhibition // Image by Taylor Justin

26. Plan an informal Friendsgiving.

27. Plant fall flowers.

28. Celebrate Oktoberfest.


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