Fall in Chicago is worth the trip all on its own: golden leaves in Millennium Park, crisp air off the lake, and apple cider donuts worth driving for. And the centerpiece of my fall calendar is Fall Fest on the Riverwalk at Island Party Hut, back every Saturday from September 19 through October 31, 2026, from noon to 8 PM.
This is one of the city’s most fun autumn traditions, and it is built for everyone. Bring your friends for fall cocktails on the water, or bring the whole family for a stress-free day along the river. Tickets are on Eventbrite starting at just $5, and buying early saves you money since prices go up as dates get closer. It is a timed-entry event, so pick the entry window that works for you, then stay as long as you like until 8 PM. Use code TWTR at checkout for a discount.
What to Expect at Fall Fest on the Riverwalk
- Hayrides on the River: Hop on a cozy hayride and cruise along the scenic Chicago Riverwalk.
- Live Music: Upbeat tunes and soulful melodies from 1 to 4 PM and 5 to 8 PM.
- Pumpkin Patch: Pick out the perfect pumpkin to carve or decorate.
- Fall Treats: Fall cocktails and craft beer, warm apple cider donuts, and hot chocolate starting in October. Word is there is a secret bar at the end of the corn maze. See if you can find it.
- Games, Photo Ops & More: Friendly competition, great photo moments, and activities for all ages.
Your ticket includes admission plus a welcome shot for guests 21 and over, or a welcome drink for kids and non-drinkers, like a Fall Shirley Temple, apple cider, or hot chocolate. One thing to know: every guest needs a ticket, including infants and toddlers, and tickets cannot be moved to a different date. So plan ahead and grab yours early.
Mark Your Calendar: HOWL-O-WEEN on October 31
The season finale on Saturday, October 31 is DOG HOWL-O-WEEN, a tail-wagging dog costume party and parade. Dress your pup in their spookiest, silliest, or most pawsome costume, catch a parade at 2 PM, 3:30 PM, or 5 PM, and enter the photo contest by tagging @IPHFallFest with #FallFest for a shot at prizes like party cruise tickets and wine and martini tastings.
Get your Fall Fest tickets on Eventbrite and do not forget code TWTR at checkout for a discount.
More Fall Fun in Chicago
Want even more fall plans? Here are a few more ways to make the most of the season:
- Explore the fall foliage: Take a scenic stroll through Millennium Park, Lincoln Park, or Garfield Park when the leaves turn.
- Visit a pumpkin patch: Pick your pumpkin and make a day of the other fall activities while you are there.
- Celebrate Halloween: Get into the spooky spirit with haunted houses, costume contests, and trick-or-treating around the city.
- Indulge in fall flavors: Savor pumpkin spice lattes, apple cider donuts, and everything warm and cozy.
Coming into town for it? My $8 guide, Your Best 3 Days In Chicago, lays out a full local’s itinerary so you can plan your trip in minutes.
Fall in Chicago is short and sweet, so get out and enjoy it while it lasts. I hope to see you on the Riverwalk. And if you are visiting from out of town, find the perfect accommodation to make your fall trip extra special.
