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My Chicago Fall Bucket List

a walk in the park should be on a Chicago fall bucket list

Above: Long walks in my favorite park– Humboldt Park! Outfit details in this post!

WOW where has the week gone? (These post-holiday weeks, man, they are always a blur!) I hope it’s flown by as quickly for you as it has for me! Seeing as September really snuck up on us, I was thinking the other day about how there are so many fun things I’d like to accomplish to get the most out of fall–one of my favorite seasons! (Although, admittedly, I’m still not ready for summer to be over!) 

I always get requests for more Chicago-centric content, so I figured it would be fun to share some items on my fall bucket list. (However, a few aren’t even Chicago related!) I hope this gives you some great ideas and inspires you to make your own! ??


Jess’ Chicago Fall 2019 Bucket List: 

Anniversary Staycation at the Waldorf 

Okay, we’re actually checking this one off this weekend. (I realize this is a bit like writing something on your to-do list after its been completed just so you can cross it off but WHATEVER! It totally counts! ?)

We’re celebrating our 2nd anniversary this weekend–it’s September 9th! ?Last year we did a staycation at our favorite hotel, The Waldorf Astoria, which is where we got engaged! We loved it so much, we wanted to make it a tradition–so we’re checking that off the bucket list this weekend. I am SO. EXCITED. I did a whole recap of our staycation last year in this post

Even if you don’t stay the night, I can’t recommend a trip to the Waldorf enough. We adore their beautiful bar and restaurant, Margaux Brasserie, and highly recommend cozying up for a cocktail there at the very least! 

Go to this pop-up corn maze bar 

I am SO EXCITED to go to this pop-up on Goose Island this year! It’s like an adult pumpkin patch (but don’t worry, kids are also allowed!) It’s a bar/corn maze/mini festival/pumpkin patch all in one. Such a great activity to do with friends, family, or with out-of-town guests! 

Squeeze in as many walks + runs outdoors as possible 

We live about 2 miles from Humboldt Park (like the park, which is, of course, in the neighborhood of Humboldt Park!) and it’s one of my favorite places ever. I love going for runs to the park in the summer, but it’s is even more magical in the fall–SO beautiful! I feel like there is such a short window we have to enjoy the beautiful fall weather, so I want to maximize it as much as possible! Goal: Grab a drink at the boathouse post-run to admire all the beautiful leaves changing colors!

Finally go apple picking! (I’ve never been!) 

How have I lived in the midwest for this long and never been apple picking!? Every time we pass Apple Holler on the highway I swear to myself that THIS WILL BE THE YEAR. So maybe in 2019, it actually will be? ?Give me ALL THE FALL HOKINESS. 

Weekend getaway in Galena 

Have you been to Galena, IL? It is the CUTEST little town just a few hours outside of Chicago–but it feels a million miles away! We went last year around this time and it was such a wonderful escape from the city. Even if it’s just for the night, it’s the perfect little getaway! Plus, it is absolutely gorgeous in the fall! See my whole Galena, IL guide here! (Also see Best Day + Weekend Getaways from Chicago!)

Do at least one more reader meet-up 

My last reader meetup (it was a “find your balance” theme with CBD + Yoga!) with Equilibria at Exchange312 was SO much fun–it also filled up within 20 minutes of being posted to IG stories–I didn’t even get a chance to post it on the blog, haha! I would love to do more of these this fall! Make sure you’re following me on Instagram, because that is where they’ll be posted first! 

Explore at least two new neighborhoods! 

Did you know that Chicago has 77 (SEVENTY-SEVEN!) different neighborhoods?! In my old age I have become so bad about never leaving my regular rotation of Wicker Park/West Loop/Lincoln Park/Gold Coast/Downtown, but there are so many other amazing places to explore! I would love to take some time to explore one new neighborhood (or at least, I mean, a neighborhood I haven’t been to in a long time!) per month for October + November. (September is basically out because we’re traveling so much! ?) I would love to re-visit Andersonville, and also get back to Pilsen–I haven’t been to either in way too long! There are also so many vintage shops I adore up north that I haven’t been able to visit in a long time! Those count, too! ?

Take a random work day off 

I used to be SO much better at this. I feel like a couple years ago, it was a lot easier to take a day or afternoon off just to do something fun by myself–but I don’t remember the last time I did this, so I would love to make this happen at least once this fall where I take some time off to do whatever I feel like–relax, explore the city, or do something that only I want to do! 

A night out at The Green Mill

I have ALWAYS, ALWAYS wanted to go to the iconic Green Mill Jazz Club, an old-school Chicago jazz club with a TON of history–stars like my favorite Billie Holiday used to perform there, and it was a popular mob hang out back in the day. (It even has an underground tunnel used by Al Capone and his boys to elude authorities). If jazz isn’t your thing, it’s also home to the famous Uptown Poetry Slam–if that’s more your style! Hoping to finally make it here once the weather gets chilly. For some reason, I feel like holing up in a jazz club has much more appeal when it’s cold outside? Just me? 

Okay–to keep things realistic, I’m wrapping up because accomplishing more than 9 things in the next two months probably isn’t that realistic. ?

Do you have any of these things on your fall bucket list? If not, I hope it inspired you to create your own!