Chicago Fall Bucket List

Things To Do In Chicago In The Fall

You guys, I don’t like Pumpkin Spice Lattes. Or anything pumpkin flavored, for that matter, unless it’s pumpkin pie and/or bread. HOWEVER (gotten back into your chair yet?), I do love fall. Of course.

Things To Do In Chicago In The Fall

Being from Arizona, I never really got to experience fall until I started school at Northern Arizona University, and even then I was so engrossed in classes and my sorority that I didn’t get to enjoy it nearly as much as I do in Chicago. This is my 3rd fall in Chi-town (eeks!) and I refuse to let another year go by without doing at least some of these activities that have been on my list! So without further ado, I present to you my Chicago fall bucket list.


Visit Madison, WI for the weekend
So many of my friends went to University of Wisconsin for college, and so many of them can never stop talking about how magical it was (you know who you are). It’s just a few hours from Chicago, and I think it’s time for a visit. Any things I have to do while there?

Go apple picking
Once again, in AZ this is not a thing. And I don’t really understand the appeal… yet. Time will tell, but for now I’m keeping a close eye on this list of places to go apple picking in Chicago, and I’m already preparing for some amazing apple cider donuts.

Host a pumpkin carving party
I LOOOVE carving pumpkins–everything except scraping out the goop. Aren’t these designs cute?!

Lincoln Park Zoo Fall Fest
This is a submission from my friend Ilana — it’s a family event, so there’s bound to be quite a few kids, but it still sounds like some good, wholesome fun! It runs over a few weekends, so chances are you can make it.

Create (another) amazing Halloween costume
Last year my roommate and I dressed as Annie and Hallie from The Parent Trap. We learned the handshake, and carried oreos + peanut butter around to the bars with us and offered them to strangers. Probably my best costume yet, so this year will be hard to top! Stay tuned.

Things To Do In Chicago In The Fall

Lakeview Taco Fest. 
‘Nuff said. September 17th and 18th on Southport. I can’t make it this year, but I thought you should know about it. Also, my good friend met her boyfriend there and are still dating, so… that festival is magical. Right, Kara?!

Northalsted Halloween Parade
I’ve gone to this every year it’s always so good. It’s in Boystown, and the cast of characters that perform is so unique and talented! I can’t wait for this year.

Chicago Botanic Garden’s Night of 1,000 Jack-O-Lanterns
I haven’t been to this before, but it looks so fun! Chicagoans — you can take the Metra there pretty easily. :)

Check out Chicago Museum Week
I’m a total Chicago museum nerd, and plan to be taking advantage of the discounts available during this week! First on my list is the Chicago History Museum. What’s yours?


Things To Do In Chicago In The Fall

Alright, fellow fall lovers… what am I missing? Let me know in the comments below! Oh and if you need me, I’ll be living in this outfit until May. This shirt is sold out, but I’ve linked identical options here, here, and here. Happy fall!


Photos: Taryn Rosenberg