The best fall activities in Chicago

Who else is ecstatic for fall to be here?  I’d love to hear about some of your favorite fall activities!Well, it’s officially that time of year again. Happy Fall ya’ll, which means it’s time to pull out all of my oversized sweaters and flannels, I firmly believe one can never have too many flannels.

I love stepping outside into the crisp autumn air, seeing the leaves starting to turn from green to red and of course pumpkin flavored EVERYTHING.

I'm ready for pumpkin season.

Yes, I’m that girl. Stop judging. I’ve even been pestering my local coffee shop about when they were going to add seasonal lattes to their menu,  I’m that obsessed. Eventually the pumpkin pecan latte was born and it is heavenly, check it out at Oromo Cafe.

If you’re planning a visit to Chicago any time of year is great but it’s extra special during the fall.   

Check out my round up some of the best fall activities in Chicago happening this year that you cannot miss!

Fall activities in Chicago

Jack’s Pumpkin Nights -A Pop Up

For an exclusive fall experience in Chicago check out this one of a kind pop up from October to the first week of November at Jack’s Pumpkin Nights near Goose Island.

Get cozy around a bonfire, sip on cider and seasonal brews and maybe get lost in a corn maze searching for those brews. Don’t miss this one of a kind opportunity inside the city where all your fall dreams will come true! Get your tickets here.

Get your sweet tooth fix at Apple Fest

Fall is a great time of year to hang out at apple festivals, drink apple cider, and visit an apple orchard!

Thammie Cascales

What better way to welcome fall in Chicago than going to an apple festival. The Lincoln Square neighborhood hosts the only apple festival in Chicago.

Wander down Lincoln Avenue and inhale the apple aromas while you shop and eat some of  amazing treats. The apple pie and hot apple cider is to die for. OH! I can’t forget about the monstrous candy apples, something about a candy apple makes me feel like a kid again.

I always have to bring home a jar of apple butter and apple cider.

Book a Ghost Tour

I can’t think of a better time of year to give yourself a little fright. Bundle up with your family and friends and go on a ghost tour. Chicago has many historical buildings that are said to be very haunted. Book with Chicago Hauntings for bone chilling accounts of Chicago’s famous ghosts and sites led by two Chicago historians and paranormal researchers.

Take advantage of Open House Chicago

Explore amazing Chicago architecture at Open House Chicago every year in October.

Max Bender

One of the best FREE Chicago attractions to do during the fall is tour some of the city’s greatest architectural achievements. At Open House Chicago some 200+ buildings are open to the public for an in depth behind the scenes tour that is normally closed to the public. 

I also highly recommend a Chicago architecture boat tour (not free but worth every penny). It’s a real crowd pleaser!

Attend Oktober Fest

Get your German fix at Oktober fest on your trip to Chicago during the fall.


If you’re looking for a TURE party, stop by Dank Haus at the German American Cultural Center to celebrate Oktober fest Chicago. Come ready to party German style dressed in your best dirndl or trachten. Maybe you’re brave enough to flex your beer muscles in the stein holding contest? Be sure not to miss Oktoberfest for a damn good party.

Go to a Magic Show

What sounds better than an evening of magic at the historic Palmer House Hotel? For an intimate, magical experience book a show at The Magic Parlour and get ready for some serious fun.

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Planning a trip to Chicago in autumn? Be sure to check out these 6 awesome fall activities in Chicago.

Who else is ecstatic for fall to be here?  I’d love to hear about some of your favorite fall activities!

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