Chicago Fall Bucketlist 2021

September 29, 2021

Fall is here and the weather is perfect in Chicago! It’s that time to get your Chicago fall bucketlist together. I always tell people September/early October is really the best time to visit! The weather is some of the best we have all year, not too hot or too cold!

So I put a list together of 10 things to do this fall around the Chicagoland area this fall for everyone! They range from free to a ticketed event.

If you like any of these or go to any, tag me on @thechicagogoodlife on Instagram!

10 things to do in Chicago this fall! Add some of these to your Fall bucket list

10 things happening around Chicago this fall:

  1. The yearly popup is back at @jojosshakebar, It starts October 1st! I think it’s one of the best pop ups they have. Milkshakes, desserts, cute decor and more!

2. One of our favorite pumpkin patches is Goebbert’s Pumpkin Patch. There is so much to do for the kids like a petting zoo, pony rides, games, food and more. Definitely buy tickets ahead of time & go early!

3. If you have never done Open House Chicago with the Chicago Architecture Center, I highly recommend! This is your chance to check out buildings and parts of the city that are normally closed to the public and learn its history, etc. It’s FREE & really cool way to explore the city. This is awesome for tourists and residents to explore the city! Tickets are required just to reserve your spot because some locations fill up quickly!

4. The @thedawsonchi has the cutest patio decorated! (double check before going if they have decorated it yet!) 

boots // leggings

5. Buy tickets for @jackspumpkinpopup starts 9/23. Kids under 4 are free! Noah loves it & he’s a great age for it!

10 things to add to your Chicago bucketlist this fall like Jack's pumpkin pop upBoots // Leggings // Scarf

6. Head to the Lincoln Square Apple fest is returning October 1st weekend! This fest is one of my favorites and definitely should be on your fall bucketlist!

7. Drink some wine at the Lincoln Park Wine fest October 8th through the 10th at Jonquil Park.

8. Visit 10 apple orchards within 1-3 hours of Chicago. You can see all of them linked here on my IG page.

9. Take a Chicago Electric Boat on the Chicago River. It’s not too late to enjoy some of the nice days. My friends and I have done this a few times! We like it because you can bring your own food, drinks and drive the boat yourself!

10. Check out Gallagher Way is having a free pumpkin party on October 28th.

There is so much happening this fall and I am glad to see things are back open again! If you also like to cook, I have some fun fall hosting ideas here!

I can’t wait to see what’s on your bucketlist this fall!


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