Looking for things to do in Chicago during the fall? I’ve got you covered! I used to think that things die down when the weather got cold, but this list will prove to you that there is still some fun things to check out even with a little bit of chill outside. Here are 10+ activities that I think are worth dealing with a cold and checking out in Chicago during the fall time:
10+ Activities You Should Try in Chicago During the Fall
Architecture River Cruise
🎟️ Admission Cost: $40–$55 per adult depending on cruise type/time.
🚗 Parking Cost: Paid parking near the docks.
ℹ️ Helpful Tip: Choose an evening cruise for a sunset skyline experience.
You can find more information about the Chicago Architecture River Cruise on the official website here.
Bike Ride on Lakefront Trail
🎟️ Admission Cost: Free.
🚗 Parking Cost: Metered parking along the lakefront or nearby garages.
ℹ️ Helpful Tip: Go early in the morning for less foot traffic and calm lake views.
You can find more information about Lakefront Trail on the official website here.
Fall Fest on Riverwalk with Hot Cider
🎟️ Admission Cost: Free entry; vendor prices vary.
🚗 Parking Cost: Metered parking or nearby garages.
ℹ️ Helpful Tip: Try the apple cider donuts from local pop-up vendors.
You can find more information about Fall Fest on Riverwalk on the official website here.
Farmer’s Markets
🎟️ Admission Cost: Free entry.
🚗 Parking Cost: Varies by location; limited street parking available.
ℹ️ Helpful Tip: Bring your favorite tote and arrive early for the best produce.
You can find more information about Chicago Farmer’s Markets on the City of Chicago official website here.
Gangsters & Ghost Tour
🎟️ Admission Cost: Around $35 per person.
🚗 Parking Cost: Paid street or garage parking nearby.
ℹ️ Helpful Tip: Bring comfortable walking shoes and dress warmly for night tours.
You can find more information about Gangsters & Ghost Tour on the official website here.
Gourmet Festival
🎟️ Admission Cost: Around $25–$40 depending on day and activities.
🚗 Parking Cost: Nearby paid garages or public transit recommended.
ℹ️ Helpful Tip: Purchase tasting tickets in advance to skip long lines.
📅 Dates: September 25-28
You can find more information about Gourmet Festival and the vendors on the Choose Chicago official website here.
Jack’s Pumpkin Pop Up
🎟️ Admission Cost: ~$22-30
🚗 Parking Cost: Limited street parking; rideshare recommended.
ℹ️ Helpful Tip: Go at sunset for the best golden-hour photos.
📅 Dates: Until November 2nd
You can find more information about Jack’s Pumpkin Pop Up and purchase your tickets on the official website here.
Night of 1,000 Jack O’ Lanterns at Chicago Botanic Garden
🎟️ Admission Cost: ~$25 online – $27 day of with a $3 fee
🚗 Parking Cost: Public Parking Available
ℹ️ Helpful Tip: Bring a tripod or low-light camera setting for glowing pumpkin photos.
📅 Dates: October 8 through the 12th, 15th through the 19th, 22nd through the 26th.
You can find more information about Night of 1,000 Jack O’ Lanterns on the official website here.
Oktoberfest
🎟️ Admission Cost: Usually $10–$20 depending on the location.
🚗 Parking Cost: Limited parking; take public transit or rideshare.
ℹ️ Helpful Tip: Arrive early for the live music and best beer garden seats.
You can find more information about Chicago Oktoberfest on the official website here.
Ride Navy Pier’s Ferris Wheel at Night
🎟️ Admission Cost: About $18 per adult.
🚗 Parking Cost: Garage parking available at Navy Pier ($20–$30).
ℹ️ Helpful Tip: The best skyline view is from the top during sunset or after dark.
You can find more information about Navy Pier’s Centennial Wheel on the official website here.
Spooky Lincoln Park Zoo Fall Fest
🎟️ Admission Cost: Free admission, but there are tickets for a specific attractions
🚗 Parking Cost: Paid parking available at the zoo lot, but parking is free on the street
ℹ️ Helpful Tip: Weekday mornings are less crowded for families with kids.
📅 Dates: September 26–October 26
You can find more information about Lincoln Park Zoo Fall Fest on the official website here.
🔗 All links create a new tab + go to the official website/social media for each event; no affiliates, no redirects, just helping you have a good time.
What did you end up picking for this weekend?
Ultimately, don’t let a little bit of chill stop you from having a good time. There’s still so much to do in Chicago and the weather is not stopping anything. If you’re looking for things to do in the Chicagoland area, I highly suggest adding a few of these to your list to check out; if you think I missed something cool that’s happening this year, comment below so I can add it to the list.
