Best fall road trips from Chicago
Fall is here, which means it’s time for the Midwest to shine! We’re lucky to live close to some of the best places to see the beautiful fall colors! Jill Halpin of LittleChicagoGuide.com shares where to go for the perfect fall getaway!
CHICAGO – Fall is here, and the Midwest is starting to show off! The colors are popping, the air is crisp, and this year’s weather is stretching out the season.
“The best thing is fall has kind of taken its time this year creeping in,” said Jill Halpin of LittleChicagoGuide.com. “So we’ve got lots of time to explore.”
What they’re saying:
Halpin joined Good Day Chicago to share five easy getaways just a short drive from the city—perfect for a weekend escape!
“Fall has everything you need for a perfect getaway,” she said. “The scenery is beautiful, the foliage makes it a little more magical, and you don’t have the big crowds.”
5 Midwest Fall getaways
Pikes Peak State Park, Iowa
Four hours northwest of Chicago, this park overlooks the Mississippi River with bluffs, valleys, and 11 miles of hiking trails. Halpin calls it “all lit up with that fall color. Beautiful, beautiful spot.”
Confluence of Mississippi and Wisconsin Rivers, Pike’s Peak State Park, Iowa (Joe Sohm/Visions of America/Universal Images Group via Getty Images)
Indiana Dunes, Indiana
A summer favorite that’s just as stunning in fall.
“You can still swim and I’m telling you it’s gorgeous,” Halpin said. “You’ve got the blue sky, the blue lake, the beautiful reds and golds and yellows. It’s so picture-postcard perfect.”
Bay View, Wisconsin
This Milwaukee neighborhood mixes city fun with small-town charm—lakefront parks, beer gardens, farmers markets, plus locally owned shops and restaurants. Halpin recommends Ursa, a boutique with carefully curated home goods and apparel.
View of the Indiana Sand Dunes State Park in Chesterton, IN. (Patrick Gorski/NurPhoto via Getty Images / Getty Images)
Saugatuck, Michigan
Known as Michigan’s Art Coast, this cozy town is lined with galleries, boutiques, and restaurants. For a workout with a payoff, climb 300 steps up Mount Baldhead for panoramic views of Lake Michigan and the fall colors.
M-22 Scenic Drive, Michigan
A 100-mile stretch along Lake Michigan that winds past wineries, lighthouses, and beaches.
“It’s just gorgeous,” Halpin said. “And this time of year it is stunning.”
Planning your trip
What you can do:
Want to make it more than a day trip? Halpin says many travelers are renting RVs and camper vans for weekend getaways. Some companies will even deliver and set up your camper at a site—no hassle required.
For families, Halpin says fall trips are a lot easier.
“You don’t have extreme heat or anything like that. So if you’ve got kids with you they’re maybe not whining—it’s comfortable. And it’s just a really nice time to get out there,” she said.
Her website also offers family-friendly and dog-friendly itineraries, with suggestions on where to stay, where to eat, and the must-see stops in each town.
And if these five destinations aren’t enough, Halpin has even more ideas: “We put together a downloadable PDF guide with 10 getaway options you can pull right up on your phone.”
For more getaway ideas—and a downloadable PDF guide—head to LittleChicagoGuide.com.
The Source: This story is based on an interview with Jill Halpin of LittleChicagoGuide.com, conducted Thursday, Oct. 2, 2025, on Good Day Chicago with anchors Brian Jackson and Kaitlin Cody.