The Ultimate Chicago Fall Bucket List: 10 Unique & Fun Things to Do This Season
Fall in Chicago is pure magic - it might be cliché to say but it is my favorite time of year. And it’s hands down and also my favorite season for fashion. The crisp air, golden leaves along the lakefront, and seasonal events make it the perfect time to explore the city. Whether you’re a local or visiting for a weekend getaway, this Chicago fall bucket list will guide you through the best seasonal activities the city has to offer.
1) TAKE A COOKING CLASS
I love taking cooking classes but I have yet to do one in Chicago. And here, there are an unlimited amount of cooking classes in the city so it’s hard to narrow it down to just one.. The Chopping Block is probably the most notable place to take a cooking class. They have an endless list of offerings from knife skills to bootcamps to specific themed-food genre classes.
If you’re more into wine and pasta (who isn’t?), Eataly hosts incredible Italian-inspired cooking and wine-pairing experiences. Both make for the perfect cozy indoor fall activity in Chicago.
2) SIP SOME SEASONAL DRINKS
If you love PSL’s, then you probably love fall flavored cocktails. And I know a few places you can try them. At the Starbucks Reserve Roastery on Michigan Avenue, they’re currently serving seasonal cocktails like Pumpkin Espresso Martinis and Apple Spiced Negronis — the perfect fall vibe.
For something more hands-on (and a little spooky), check out Frankenstein’s Mad Scientist Cocktail Lab — an immersive Halloween pop-up where you actually get to “finish” your own creepy cocktails.
3) WATCH A BEARS GAME
Fall means football. Even if you don’t like sports lol. But I do love going to sporting events because I like the vibe, the snacks, and the most important part: the tailgate’s! There’s nothing like cheering on the home team at Soldier Field. I’ve never been to a Bears game myself, but this might finally be the year, especially now that Simone Biles’ husband plays for the team :)
4) LAUGH AT A COMEDY SHOW
Chicago is a comedy capital. Second City is such an iconic theatre where all your favorite comedians have put their time in on stage. What’s better when it’s cold outside than to be inside laughing at comedians?!
For something different, try Drunk Shakespeare — an interactive show where one actor takes five shots of whiskey and attempts to perform Shakespeare while the rest of the cast tries to keep the play on track. It’s chaotic, hilarious, and totally worth adding to your fall in Chicago bucket list. It’s definitely on mine.
5) EXPLORE A PUMPKIN PATCH
Yes, I know it’s basic but so what? It’s fun!!
Yes, it’s basic — but who cares? Pumpkin patches are pure fall fun. You can make a day trip out of it and head to Goebbert’s Pumpkin Patch or stay local with Jack’s Pumpkin Pop-Up in the city. The epitome of fall is picking pumpkins, sipping cider, or snapping fall photos.
6) ENJOY A TASTING DINNER
There is 1 tasting menu I have my sights set on: Class Act. It’s a newer concept where you are sat at a community table and served a multi-course tasting menu. EThis is also the PERFECT solo date idea. You can enjoy a meal with a group of people and make some friends vs. sitting alone at a table.
7) TAKE A HAUNTED CHICAGO GHOST TOUR
A ghost tour is the ultimate spooky activity. Chicago Ghost Tour is the perfect way to get in the Halloween spirit. There are tons of options — from walking tours through haunted neighborhoods to boat tours along the river that explore Chicago’s darker side.
8) SEE A BROADWAY PLAY
Call me a theater nerd but I love a Broadway show. Check the lineup on Broadway in Chicago for the latest performances. This season, I have my eye on Six, and honestly, it’s also one of the best solo activities in Chicago if you want a cozy, cultural night out.
9) TRY A CANDLE-MAKING CLASS
Fall scents are probably my all-time favorite. Pumpkin, vanilla, bourbon, it’s the best scents! It’s so hard to find the most perfect candle so why not make your own? Take a workshop at AURA Candle Bar or Chicago Candle Studio to pour your own signature scent.
10) LISTEN TO MUSIC AT SALT SHED
For the perfect end to your Chicago fall adventures, grab tickets to a show at The Salt Shed. The riverside venue hosts an incredible lineup of concerts and events, combining industrial-cool vibes with skyline views — especially stunning under the fall sunset.
Fall in Chicago doesn’t have to be about drinking. There are plenty of ways to try new things, and soak up the beauty of the city before winter hits. Whether you’re sipping a pumpkin cocktail, cheering on the Bears, or making your own candle, this Chicago fall bucket list is packed with activities that make the season unforgettable.
