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30+ Not to Miss Midwest Road Trip Destinations

Whether you’re looking for family fun, outdoor adventures, or city exploring, every state in the Midwest has something to offer. Each state has something different to explore, from historic sites to outdoor activities. These are some of our favorite Midwest road trip destinations that shouldn’t be missed!

Midwest Road Trip Stops - Kids Are A Trip

Best Stops on a Midwest Road Trip

I love the Midwest because it’s full of hidden gems! From small towns along the Great Lakes to quirky roadside attractions, there are endless attractions for families. This list should be used as a starting point for planning your Midwest road trip. We’ve picked starting destinations, what there is to do there, and where to stay. Use these ideas to start your own Midwest road trip adventures.

Midwest Road Trip Map

Illinois Road Trips

Chicago

Sitting on the shores of Lake Michigan, Chicago is a must visit destination for all ages. Not to miss spots for families include Maggie Daley Park (with an ice ribbon in winter) and Millennium Park, the Museum of Science and Industry, Navy Pier, and an architecture river cruise on the Chicago River.

You can buy a CityPASS that will give admission to the Shedd Aquarium, SkyDeck Chicago, and Field Museum, as well as two others at a discounted rate (choosing between The Art Institute, Museum of Science and Industry, and 360 Chicago Observation Deck). This is a great way to save money in Chicago.

Chicago River Architecture Cruise-Kids Are A Trip

If you need more ideas, these are our favorite things to do in Chicago with kids!

Where to stay: We have an entire list! These are the best places to stay in Chicago with kids.

Galena

Galena is one of the most charming towns in Illinois. Located near the Great River Road that runs along the Mississippi River, this is an opportunity to step back in time. The Main Street is lined with 19th century buildings, old fashioned shop signs and billboards, and small, independent businesses.

Fun things to do in the area include a trolley tour, hot air balloon ride, and star gazing. Nearby Chestnut Mountain Resort offers zip lining in the summer and skiing in the winter, so it’s perfect year round!

Where to stay: Jail Hill Inn is a former jail and has been named the best B&B in the US by TripAdvisor!

PLANNING A ROAD TRIP? DON’T MISS OUR ROAD TRIP PACKING LIST!

Springfield

Springfield was the home of President Abraham Lincoln and a perfect stop on Route 66 (it runs from Chicago to Los Angeles). Families will enjoy seeing where Lincoln lived, the Lincoln Tomb, and the Illinois State Capitol building.

Where to stay: Hotel Vandivort is a boutique hotel housed in a former masonic temple that is walking distance to many major attractions.

Starved Rock State Park

This is a great place to visit if you’re looking to escape the city. We recommend a visit in the spring to see the amazing waterfalls in full flow. Take a walk along the water at French Canyon which is 4 miles from the Visitor Center, then you can go onto Lover’s Leap viewing platform.

Fall Colors From a Cave in Starved Rock State Park in Illinois

Note: Although some hikes are on even ground, there are a lot of stairs so come prepared. 

Where to stay: There are campsites, but if that’s not your thing, Starved Rock Lodge is nice and cozy. 

Wisconsin Road Trips

Door County

One of my favorite places to visit in Wisconsin is Door County. Located on a peninsula between Green Bay and Lake Michigan, the area is made up of charming small towns, stunning state parks, and miles of trails for hiking. They also have the famous Wisconsin fish boils, fruit picking in the summer, cute local shops, and vineyards.

Visitors to this Wisconsin peninsula will not be disappointed. Here's what not to miss in Door-County-with-Kids.-Kids-Are-A-Trip

Visitors won’t want to miss a scenic drive here any time of year, but in the fall, it is particularly magical. Don’t miss our favorite things to do in Door County in summer.

Where to stay: Many people choose to stay in a vacation rental home in Door County, but we also like the White Gull Inn in Fish Creek.

Lake Geneva

Located two hours from Chicago and an hour from Milwaukee, Lake Geneva was built by wealthy Chicagoans looking for a country escape in the 19th century. Today you can walk around the lake and admire some of the stately homes, stroll down Main Street, or try one of their golf courses. There’s beaches, horseback riding, hiking trails and more, so families won’t mind spending more than a few days here.

Where to stay: Grand Geneva Resort is located just outside town, offering golf, a waterpark, and spa. In the winter there’s skiing, sledding and holiday events.

Milwaukee

Milwaukee is a city that is constantly evolving. Families will love the Milwaukee County Zoo, Harley-Davidson Museum, Discovery World, and the public markets. Don’t miss Sprecher Brewery where mom and dad can try some adult beverages while the kids sample craft sodas. It’s the perfect place for a weekend road trip from the Windy City.

Those who have been to Milwaukee know it's anything but ordinary. Here are the best things to do in Milwaukee in a weekend that you wouldn't find elsewhere.-Kids Are A Trip
Visit the Historic Third Ward and tour the Public Market.

Where to stay: We’ve enjoyed Homewood Suites Downtown and The Pfister is an elegant Victorian era hotel that is popular with tourists.

Wisconsin Dells

Families who love to spend time in the water won’t want to miss Wisconsin Dells, home to a massive number of water parks! Noah’s Ark Waterpark is the world’s largest outdoor waterpark covering over 70 acres. It’s a must visit during the summer. Other popular parks include: Kalahari, Chula Vista, Mt. Olympus, and Wilderness Territory.

If waterparks aren’t your thing, there’s Circus World (all about the Ringling Brothers), miniature golf, Devil’s Lake state park, and the Wisconsin deer park.

Where to stay: Waterpark fans should stay at Kalahari Resort to enjoy its massive indoor waterpark. Non-water enthusiasts should consider the SpringHill Suites.

WANT TO ENTERTAIN KIDS ON A ROAD TRIP? DON’T MISS OUR FAVORITE ROAD TRIP ACTIVITIES!

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Indiana Road Trips

French Lick

French Lick and the neighboring town of West Baden, are a pleasant surprise for most visitors. In the mid-1800s, two major hotels were built, one in each town, and the area’s mineral springs were advertised to attract visitors to the resorts.

Today, one is a casino/hotel and the other is a luxurious reminder of the past. After you’ve explored the resorts, don’t miss your chance to bathe elephants at Wilstem Ranch, explore Marengo Cave, play golf, experience the local wine trail, or head to Holiday World amusement park. This was one of our family’s all time favorite vacations.

Where to stay: Both West Baden Springs and French Lick Resort are worth a stay. They share amenities, so it really just depends on your family. West Baden Springs is the more formal of the two, and French Lick Resort has a casino.

Indiana Dunes National Park

One of the newer national parks, Indiana Dunes is a perfect Chicago day trip or weekend getaway. The park’s sand dunes border Lake Michigan and there are 50 miles of trails to explore, both near the shore and in the woods. When you’re finished, spend your time exploring the south shore of Indiana where you’ll find shopping, zip lining adventures, and a small zoo.

Indiana Dunes National Parks-Kids Are A Trip

Where to stay: We loved Beachwalk Vacation Rentals in Michigan City where you can rent a home and have access to the beach, a pool, clubhouse, and more.

Indianapolis

Indianapolis is another underrated Midwest destination. The city has been undergoing a rebirth, and it’s an amazing thing to see. Don’t miss the Children’s Museum of Indianapolis with both indoor and outdoor attractions, take a walk (or bike) through White River State Park, and don’t miss the Indianapolis Zoo.

There’s also a duckpin bowling alley (Action & Atomic) and an historical village where kids can experience a living history museum.

Where to stay: We love the JW Marriott which is right next to Victory Field and White River State Park, and walking distance to Lucas Oil Stadium (home of the Indianapolis Colts).

Michigan Road Trips

Mackinac Island

If you’re a fan of romantic destinations, Mackinac Island might be one of the best road trip destinations in the Midwest. Mackinac Island sits between the lower and upper peninsula of Michigan in Lake Huron. As it’s an island, you’ll need to take a ferry to reach it from Mackinaw City or St. Ignace.

Mackinac Island - Kids Are A Trip

Once you arrive on this car-free island, you’ll see people on bikes, and even horse taxis, but most people use their feet to get around. You can hike to Arch Rock, explore the whole island by bike, and find a place for a picnic. Don’t forget to try the island’s famous fudge. 

Where to stay: The iconic Grand Hotel. It’s the place to stay at this magical Midwestern getaway.

Traverse City – Sleeping Bear Dunes

If you visit the Traverse City area, one of your first stops should be Sleeping Bear Dunes National Lakeshore which is about 40 minutes away. It’s a lot of work to climb up the dunes, but kids will love rolling down the hills and playing on the beach once they reach it.

After you’ve climbed the famous dunes and completed the trail, head back to Traverse City for some more action. In the summer, you can rent bikes and take one of their many trails, or in winter you can ski cross country at night!

Where to stay: Cherry Tree Inn and Suites offer a luxury stay, with a private beach on the lake, lots of kids activities and shuttles around the city. 

Missouri Road Trips

Kansas City

If you’re a Speedway fan, you have to time your visit to this Midwest road trip destination with a Speedway day. Speedway not for you? You could catch a Chief’s game, or tour some of the many museums in Kansas City. The National World War I Museum, Negro Leagues Baseball Museum, and Money Museum are all worth a visit.

Where to stay: The 21C Museum Hotel is a beautiful boutique hotel that’s perfect for a family stay.

Lake of the Ozarks 

Great for families who love adventure and activities. If you don’t own a boat, no problem, lots of businesses rent out kayaks, speed boats, and jet skis. You can parasail, explore caves, hit the water park, and spend an afternoon at the skatepark. 

Lake of the Ozarks-Kids Are A Trip

Where to stay: There are lots of large vacation rentals for families who want to be on the lake.

St Louis

If you are taking a Midwest road trip, St. Louis is a city that shouldn’t be missed. It sits on the banks of the Mississippi River and you can’t miss The Gateway Arch in the city’s skyline. Families will love exploring City Museum, with plenty of hands-on exhibits. Housed in a former warehouse, artists repurposed parts from all over the city to create a world of wonder. There’s slides, tunnels, and even a Ferris wheel. Don’t miss a chance to explore this with your kids!

For a fun day out grab some food from Soulard Farmers Market and head to Forest Park where kids can skate, boat, or head to the zoo. The Saint Louis Zoo is one of those rare free zoos, and kids will love the penguins and train ride. 

Where to stay: The Hilton at the Ballpark has the perfect location. It’s walking distance to restaurants and the Arch, and you can see into the St. Louis Cardinals stadium!

DON’T MISS OUR FAVORITE STAYCATION IDEAS!

Ohio Road Trip Stops

Cincinnati

When you reach Cincinnati, head straight to the Observation Deck at The Carew Tower. You can get a great overview of the city and spot where you’re going to go next. Will it be a Bengals game? Or King’s Island Amusement Park? For an educational element, go to the National Underground Railroad Freedom Center, the American Sign Museum, or the Cincinnati History Museum.

Where to stay: The Renaissance Cincinnati for beautiful art deco style and great service.

Cleveland

Our first recommendation in Cleveland is the Rock and Roll Hall of Fame. Kids will love the hands-on exhibits and learning about music through the years. Next door is the Great Lakes Science Center, which kids will love as well. Both have beautiful views of Lake Erie.

If you’re looking for something a little different to do in this Midwest road trip destination, the SuperElectric Pinball Parlor should be your first stop for some family fun! It’s just one of many unique things to do in Ohio!

Cleveland downtown sunset-Kids Are A Trip

During the day you can head out in search of the vibrant street art, and when it’s time for food, head to Westside Market. You can take a food tour, or just follow your nose. 

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Where to stay: The Hyatt Regency Cleveland at The Arcade is close to many of the city’s attractions.

Hocking Hills State Park

Make a stop here for its waterfalls, gorges, ziplining, and… a pencil sharpener museum! The park ticks so many boxes for those who want to stroll along the river, walk to the edge of the highest part of the park, or relax on the Hocking Valley Railway. 

And if you’re interested in looking at a collection of over 3,000 sharpeners, head to the Paul A. Johnson Pencil Sharpener Museum. We think you’ll be in for a treat!

Where to stay: You could camp, but you could also stay in a treehouse! Check out, Among the Trees Lodging or Hocking Hills Treehouse Lodge.

South Dakota Road Trip Stops

Badlands – Mount Rushmore – Deadwood

A South Dakota road trip to Badlands National Park is a popular vacation for Midwesterners. Badlands is one of six National Parks in the Blackhills region.

As you drive along Badlands Loop Scenic Byway, keep an eye out for bison, prairie dogs, and deer. Popular parts of the park include the Yellow Mounds Overlook, Pinnacles Overlook, and the Sage Creek Rim Road.

Be sure to allow plenty of time for kids to scramble over the unique rock formations.

Mount Rushmore is only a 1.5-hour drive from Badlands, so that shouldn’t be missed. You can make it a day trip or stay for a couple of days. Mount Rushmore has marvelous sights, including: faces of our Founding Fathers, the Avenue of Flags, Presidential Trail, and the Lincoln Borglum Visitor Center.

Badlands -Kids Are A Trip

Another unique place in South Dakota is Deadwood. Located in the Black Hills National Forest, the town has a rich Wild West history and ties to the gunslinger Wild Bill Hickok. There are numerous events throughout the year, including the Sturgis Motorcycle Rally and “Wild Bill Days.”

Be sure to stop at the Crazy Horse Memorial and learn about Native American Culture at their museum. Custer State Park is another must see stop in the area with plenty of outdoor fun.

Where to stay: If you want comfort then book a cabin with The Badlands Cedar Pass Lodge

Must Visit Road Trip Stop in Kansas

Wichita

The centerpiece of the city is the Keeper of the Plains, a dramatic 44-foot tall steel sculpture of an American Indian donated to the city by its creator, Francis (Blackbear) Bosin. The sculpture lights up with a “Ring of Fire” every evening which you can see for free. 

Head to the Riverside Park which has a great children’s play area with a wildlife section the locals call “The Zoo”. There are 25 species from owls and hawks to porcupines and beavers, all can be seen for free too! Don’t miss a chance to hand-feed the lemurs at Tanganyika Wildlife Park and Exploration Place science center.

Where to stay: Ambassador Hotel offers spacious rooms and breathtaking views.

Nebraska Road Trip

Omaha

Omaha’s Henry Doorly Zoo and Aquarium is one of the best in the country, so you won’t want to miss it. Be sure to try the Sky Safari and see the zoo from above. Explore the shops and galleries of the Old Market, head to the Wildlife Safari Park, or take a stroll on the Bob Kerrey pedestrian bridge for beautiful city views overlooking the Missouri River.

Omaha Nebraska - Kids Are A Trip

Where to stay: Hotel Deco is a stunning boutique hotel with easy access to restaurants, shops, and the Old Market.

Minnesota Must Visit Sites

Boundary Waters

This is the top road trip destination in the Midwest if you love canoeing. When I say this, I mean traveling around the area with camping gear by canoe for days at a time. There’s lots of advice out there for beginners, and you’ll want to reach out to a wilderness outfitter if you’re thinking about a trip. This adventure is a great way to spend time as a family and get away from screens and technology! 

Where to stay: In a tent at one of the many campsites along the route. 

Grand Marais

Located between the Sawtooth Mountains and Lake Superior, one visit will show you why people like Grand Marais. This artist community is the oldest in Minnesota and it attracts musicians, photographers and artists from around the world. The shops sell locally made gifts and art, and Artist’s Point has some incredible views of the water and unique rock formations.

Grand Marais - Kids Are A Trip

Where to stay: Best Western Plus Superior Inn has newly renovated rooms and gorgeous lake views.

North Dakota road trip

Rendezvous Region

North of Grand Forks is the Rendezvous Region, the perfect stop on a North Dakota road trip as it is make for adventure lovers. In the summer families can enjoy hiking, kayaking, and horseback riding through the state parks. Don’t miss the Pembina Gorge State Recreation Area, kayaking the Pembina River, and spending time on the lake at Icelandic State Park.

North Dakota Road Trip-Kids Are A Trip

Where to stay: One Majestic Place offers vacation rentals that are perfect for families.

Theodore Roosevelt National Park

Located in western North Dakota, Theodore Roosevelt National Park offers stunning views of the Badlands from its scenic byways. Loop roads mean you can get great views without the need to hike, making it accessible to all. If you do want to hike, trails range from the short but steep Buck Hill to the 10 mile Petrified Forest Loop. For a true Old West experience, head to nearby Medora for some rootin’ tootin’ fun!

Where to stay: Rough Riders Hotel “mixes luxury with Western Charm”

Iowa Road Trip Stop

Des Moines

Start at the Pappajohn sculpture park with 24 sculptures that are perfect for photos and take a self-guided tour of the street art murals around downtown. Spend time at the Downtown Farmers’ Market shopping for treats or the Greater Des Moines Botanical Garden and its beautiful bonsai tree collection. Other fun sites to visit include the High Trestle Trail Bridge and the Iowa State Capitol Building.

Where to stay: Surety Hotel has a great location in the heart of downtown.

Some of the best road trip destinations are in the midwest, making them accessible from lots of places in the United States. If you’re not already a road tripping family, you really should consider one of these road trips in the Midwest!