Fall-ing for Chicago

Now that I’m back in Illinois, it does get hard to remember that all the seasonal things I got used to in Seattle (like the Washington state fair and fall foliage) don’t look the same here. But while I miss those bangers, I did manage to fill my October with some un-skippable fall festivities. Let’s just say that I jam packed my weekends over the last two months almost as much as I’ve jam packed my apartment with Halloween decor!

Instead of doing a top ten list, I just thought I’d rate ALL the fall things I did this year. I’ve been been watching a lot of four weddings and that makes me want to be a TV host and mimic that format, so I’m scoring all the things off the overall experience score, which factors in the value for money. Let’s get started!

1.) Richardson Farm

Score: 9

Richardson is an awesome experience for the whole family, with everything from zip lining to getting to hold adorable baby chicks. The thing that they’re known for though is the largest corn maze in the U.S by square footage, with three different types of trails you can take on. My favorite was the Quiz trail, where you can answer themed trivia questions (there was a kids, sports, and science based trivia when we visited) to unlock the right way to go next. It’s $30 for general admission, which includes the corn maze, train, and animal barns, but there’s a lot more elements you can add on as well. There was a really neat glass blowing booth that was a highlight, along with their delicious fall drinks and treats.

2.) Fall Foliage on the 606

Score: 7

The only reason for the slightly lower score is that it is just looking at trees which I guess you can do anywhere, but I love looking at trees, so I would highly recommend this one. I live just off the 606 (aka Bloomingdale trail) so one of my favorite weeknight activities has been just strolling it and watching the leaves change color. It’s such a great way to decompress and I may or may not be doing it as I type this out:)

3.) Chicago Ghost Tour

Score: 10

If there’s anything on this list that I can super recommend you try, it’s going on the Chicago Boos and Booze Ghost Tour in Lincoln Park. I believe this is also available in other major U.S cities (I actually did it while back in Charleston in 2022) but I preferred this one! There is so much insane history around Chicago, particularly the spooky cemeteries and haunted bars of Lincoln Park. It’s $30 and the tour guides (we had Katie) are so knowledgeable so it is worth it! I don’t think my goosebumps went away the whole time!

4.) Chicago Open House, Glass Blowing in the Pumpkin Patch

Score: 8

I’m sure a lot of you are familiar with Chicago’s open house weekend, where they open some private institutions to the public for the weekend. My mom recommended I visit Ignite Glass Studios and I loved it! They had a glass demo, a “pumpkin patch” gallery, and a gorgeous rooftop open for viewing. Such a fun, unique experience and the artists are SO talented there! They have a Friday show the first Friday of each month where they have a demo and offer glass blowing workshops as well, so highly recommend.

5.) Boo-Palooza

Score: 3

This is a small event located in Wicker Park with pumpkin decorating, community booths, music, and lots of candy! The reason it has such a low rating is that it’s definitely made for young kids - there were so many screaming children that made it difficult to enjoy the morning. That being said, there were some adorable redeeming pets dressed up and I also decorated a pretty adorable pumpkin.

6.) Goeberts Farm

Score: 6

Located in Pingree Grove with another location in Barrington, this is yet another fun fall farm/pumpkin patch with a ton to do. I personally thought when comparing it with Richardson though that there just wasn’t a ton of diversity of activities for older people-more stuff for kids! However, we did ride a hayride and pick some apples, and that was a blast! My biggest advice is to just go a little earlier in the year (September instead of October) so there’s more apples to pick from while they’re still ripe!

7.) Jacks Pumpkin Pop Up

Score: 5

One of the most hyped-up activities in Chicago potentially, Jack’s is a perfect October experience with pumpkins to choose, tons of photo ops, fun fall drinks, and a corn maze and other fun activities. My biggest disappointment with this is the value for money- there’s so few things built into the general admission! I’d say only go if you’re really into pictures, because the photo set ups are very cute, but that’s truly the only thing that’s free. The food is expensive, and all the fun carnival games, axe throwing, and other things you want to do are extra. So come prepared to spend a lot of money or I wouldn’t come at all.

8.) Movies at the Rooftop Cinema Club

Score: 9

OMG onto a great one! Since Halloween fell on a Thursday this year, my friends and I decided to spend it at Rooftop Cinema club watching Hocus Pocus. And I’d do it again a million times. The view is gorgeous, you get headphones to volume adjust to what’s comfortable for you, there’s fun snacks and drinks you can grab before the movie… all making for the coziest experience possible. I also saw Mamma Mia a few weeks ago there and I can confirm they don’t miss. RCC just wrapped for its 2024 season, but come next year, definitely check out their website because they have movies of all kids for all ages every single day.

9.) October Cafe

Score: 8

I heard about this one through TikTok and say what you will about that, but TikTok delivered! This small but memorable cafe is located in Norwood Park, Chicago and is open year round, but they specialize in fall drinks and eats, most notably their fall flight, which comes hot or iced to enjoy. We loved this spot for a fresh fall morning and the area is super cute too!

10.) Taylorween

Score: 9

This past Friday, my friends and I rounded out October with Taylor-Ween at Fatpour in Wicker Park, where we jammed to all of Taylor’s music with amazing other swiftie strangers. I loved everyone’s fun costumes and truly I don’t think there’s anything better than meeting people who can bond instantly over a shared love of ~objectively~ the best music ever.

Honorable Mentions (either didn’t make the cut or didn’t get to try this time around).

Hot Chocolate from Anne’s walks

Nightmare on Clark Street

Bergots Farm

Wicked Drag Brunch @ Kit Kat Lounge (this was one of the best things I did in October but not sure if it qualified as a “fall festivity”)

Fall Fest on the Riverwalk

Graceland Cemetery Nature

Howl at the Moon Halloween Party

Wrigleyville Halloween Bar Crawl

Art in the Dark

Haunted Halsted Parade

Streeterville Cat and Dog Parade

Buffy Vampires vs Slayers 90s Night

I will be dedicating November to seeing some cool spots around Chicago and filling you guys in on what I find, so let me know if there is anything you guys think is super worth me checking out!

I hope everyone had a safe & exhilarating Halloween week and will be back soon with another update!

Next
Next

Exploring Western Chicago