10 Fall Road Trips from Chicago

August 26, 2022

Fall road trip season here and it’s my favorite time to explore new midwest towns! There are so many places under 4 hours from Chicago to visit for changing leaves, things do, eat and see. Below is a list of a few places we have been and think are great this time of year!

Saugatuck, MI

One of my favorite road trips is to Saugatuck, Michigan! Maybe the best time of the year to visit is fall. In fact, it’s the only time we have been! It’s beautiful! It’s about 3 hours away from Chicago and there is so much to do. Dune rides (for a little older kids), beaches, lots of great restaurants, ferry ride, shops, & art galleries! There’s Crane’s Orchard which we apple picked, went on small rides, did a corn maze, etc. We even hiked the Saugatuck Dunes with both kids, the trails are pretty easy. I have two full blog posts here- for families or a couples trip to the area!

Take the ferry ride in Saugatuck.
Crane's Farm is a 3 hour drive from Chicago and great for apple picking. It's the best fall road trip destination!
Downtown Saugatuck makes a great road trip in the fall from Chicago!


One of our most favorite getaways is Galena! I feel like it makes the ideal fall road trip. The town is really old and set’s the perfect backdrop for fall! They also throw their annual Halloween parade every year and it’s the largest in the midwest! We have done it and it’s very fun! The town goes ALL OUT for Halloween!

They also have Octoberfest happening October 1st, Galena Country Fair October 8th-9th, and the 43rd annual parade in October 29th.

It’s an easy drive – just a little over 3 hours from Chicago with lots to do and see. We have stayed at an AirBNB or the townhomes at Eagle Ridge Resort, which is then a short drive to downtown. But they do have a shuttle service during Halloween weekend (or at least used to!). Grab a coffee and take the trolley on a scenic, historic tour of Galena where you’ll see many of the original early nineteenth century buildings. You can do yoga with or take a walk with goats, and then shop the small boutiques & cafes that line the main streets. I love Bread and Vine for breakfast, brunch, or lunch, Isabella Ltd for gifts and home decor, bloody mary’s at Fried Green Tomatoes and Poopsies for toys and gifts.

People start to line up super early in the day for the parade and everyone dresses up!

Rockford, IL

Rockford, Illinois is just about under 100 miles northwest from Chicago. We love to walk through and see the 12 acres of gardens, waterfalls, ponds, and tea house at the Anderson Japanese Gardens, @andersonjapanesegardens. This is BEAUTIFUL in the fall with the changing leaves. Perfect fall road trip. They do close October 31st, so make sure you go before then!

When you’re ready to fill your belly, head over to The Norwegian, @thenorwegianrockford, which is only a 3 minute drive from the Gardens. They serve delicious drinks, brunch, and dinner in the summer. Don’t skip the Danish pancake balls and housemade jam! Walk off your meal and shop next door at the cutest midcentry modern shop, Rooted, @rooted_rkfd, for gifts and home decor.  If the weather is good and you’re there on a weekend, check out The Top Rooftop Bar & Lounge at Embassy Suites for views of historical downtown, drinks, and apps! If you’re traveling with kids, you can’t go wrong with the Discovery Center Museum. If you are a member of any Illinois children’s museums, you can get into this one for free! It’s especially great for ages 5-12 with lots of hands-on STEAM activities. Highly recommend!

Milwaukee, MI

Milwaukee, Wisconsin is SO close to Chicago which makes it such an easy fall road trip day! MKE serves up great restaurants with lots of shopping! You can brewery hop or walk around downtown. If it’s a cooler day, visit the Public Market for some wine while you shop cheeses, breads, etc. Lakefront Brewery is also popular and you can sit outside on their large patio. Visit Broadway Paper (paper and gift store) and MOD GEN (gorgeous plants), and then brunch at the popular and delicious Sweetdiner! This can be done in a day or stay for the weekend! I’ve taken the Amtrak there and it’s such an easy ride!

Sawyer/Three Oaks, MI

Located just outside New Buffalo, MI, Sawyer and Three Oaks are such cute cute towns! You can do a whiskey tasting at Journeyman Distillery. We did one (I was the DD) and we loved it! They give a full tour of the grounds and it’s beautiful. There’s small pumpkin farms, bakeries along Arrowhead Highway (Swedish Bakery is so good!) and we love stopping at Sawyer Garden Center. It’s also right next to Greenbush Brewery, which is great for tastings, love their food and have an outdoor area!

Either stop by Indiana Dunes or the Galien River County Park which is pretty cool for taking long walks! The trees are just beautiful!

Galien River County Park

Sawyer Market has everything from Christmas trees, wine, decor, snacks and more!

Starved Rock/Matthiessen Park, IL

I just recently went to Starved Rock, Illinois and had the best time! It is about 2 hours away from Chicago and a pretty easy road trip! It’s great for hiking with or without the kids. I would recommend taking older kids though, because part of the trail is pretty difficult. It took about one hour each way to complete one hike. Then, there is a restaurant we grabbed lunch at on the top of Starved Rock. It was pretty good and had pretty views of the canyon!

I haven’t been to Matthiessen but I had so many suggestions after I posted Starved Rock to check it out. It’s close to Starved Rock, apparently less crowded and the trails are easier for kids!

You can also stop by the town of Utica on your way out and it’s so cute! It’s small but there are cute shops and wineries to check out.

I have stayed at Camp Aramoni, which is not far from Starved Rock. These are tents that are totally built up on the inside with several beds, air conditioning, bathroom and more! I would say this is much more of a luxurious type of trip and pricey. They do book up fast! I think it would make a fun girls trip to all split a tent!

Camp Aramoni is easy to get to from Chicago and makes a great fall road trip destination! Outside of the tent at Camp Aramoni

Camp Aramoni is easy to get to from Chicago and makes a great fall road trip destination! Inside the tent at Camp Aramoni

Holland, Michigan

It’s just the cutest little town! There’s so much to see and do between the dunes, the beach, the tulips and the windmills! It’s definitely an even better place to visit in the fall too! Downtown Holland has many great restaurants and shops. Don’t miss Lemonjello’s for college shop vibes, coffee and pastries, The Holland Peanut Store, an old school candy shop, Neli’s Dutch Village, a Netherlands theme park with a great gift shop, and Deboer Bakery for amazing cronuts. For dinner, we love New Holland Brewery, Boatwerks (the only waterfront restaurant in town), and Beechwood.

Marquette County, Wisconsin

A Wisconsin Supper Club about 10 minutes from the campground

Manny and I did this trip together a few months ago and to our surprise, we really had such a great time! I worked with Travel Wisconsin on this project and I am so thankful! This is a very, very small county in Wisconsin, about 3 hours away from Chicago just outside of Madison. We stayed at Lake Arrowhead Campground. This is nothing fancy! You can tent or rent a trailer, our’s was really nice! It’s in a completely wooded area close to water. There were wild turkeys, hens, deer, etc. In the fall, I bet it’s beautiful with all the changing leaves. Make campfires, go to Wisconsin Supper Clubs, check out Amish country (one of the best bakeries I’VE EVER BEEN TO was on this Amish farm!) and really unplug surrounded by nature.

Marquette County makes an easy road trip idea! They have AC, small kitchen, bathroom and this one had two tiny bedrooms

Oregon, IL

We took a family road trip to Oregon, Illinois two years ago in September and stayed at @pinecreekescape cabins. They are fairly big, come with a fire pit, grill and on a pretty big area of land. These are log cabins across from White Pines State Park and so pretty to hike among the changing leaves! There is a playground for kids and there are different leveled trails from easy to difficult. Check out the Bison at Nachusa Grasslands where you can see Bison roam free. It’s pretty cool! There’s really not much else to do but disconnect and be outside!

These log cabins are so cute with a wooded backdrop for the perfect fall road trip from Chicago!
Oregon IL makes a great fall road trip from Chicago

Hobart, Indiana

I am including this on the list for two reasons. There is an apple orchard (County Line Orchard) and pumpkin patch/produce farm (Johnson’s Produce Farm). You could literally do all the fall activities in one day. We did Johnson’s Farm and then visited the town, Valparaiso, which is maybe 20 minutes away? It’s got cute shops and restaurants. There’s Four Father’s brewery and a winery too! You could totally spend a full day doing all of this.

Indiana Dunes State Park, IN

This is such an easy, day fall road trip from Chicago! It’s for hiking and getting some fresh air at the Indiana State Dunes State Park! Over 2,000 acres and trails that overlook Lake Michigan, it’s a quick trip from Chicago to see some leaves changing!

Madison, WI

Lastly, check out Madison, WI and catch a Wisconsin Badger game, check out a brewery or winery, and tons of their great restaurants. One of the breweries, Olbrich Biergarten is along Lake Monona to celebrate Oktoberfest. There are also lots of pumpkin farms and apple orchards in the area too!

Hopefully some of these have inspired you to hit the road for fall road trip season! If you need other fall things to do, check out my fall bucketlist here!


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