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Looking for an epic road trip idea? Look no further than the beauty, quirky road side oddities and historical sites you’ll find on a Midwest road trip. From the urban wonders of Chicago, St. Louis and Detroit, to the natural wonders of South Dakota,, to a car-free island to a charming Christmas-themed amusement park, these epic Midwest towns and cities are our favorite Midwest vacation spots.
Our State-by-State Road Trip Guide to Midwest Vacation Spots
Having lived in the Midwest my entire life, it’s sometimes entertaining to hear what other people think about the region. Heck, I get it. I grew up in Cincinnati, Ohio, and thought for much of my young life that the rest of the state was made up of teeny towns with unpaved dirt roads.
A Midwest road trip can offer things you won’t find anywhere else — from friendly big cities perfect for a Midwest weekend getaway to unique natural wonders you can only find in the middle of America.
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Here are some of our favorite Midwest vacation spots, from Ohio to South Dakota with lots of great family friendly attractions in between.
Midwest Road Trip: Illinois Destinations
Any Midwest road trip would be incomplete without a trip to the Windy City, with its countless ways to spend your time. Here four are of our favorite must-dos during a Midwest weekend getaway to Chicago:
Visit the Bean. The shining star of Chicago’s Millennium Park, snapping a selfie in the reflective surface of the giant sculpture is a Chicago must-do. (Even the locals do it!) If you can’t show that photo when you get home, no one will believe you visited Chicago!
Go shopping. The big draw is the world famous “Magnificent Mile,” Michigan Avenue’s shopping strip. Don’t forget to stop at the American Girl Store. Even if you don’t have a daughter, the huge, luxurious store is an experience.
Enjoy the lake. Spend some time strolling along Oak Street Beach, with the magnificent Lake Michigan on one side and some of Chicago’s priciest real estate on the other. Or take a boat ride that leaves from the family-friendly Navy Pier. For a deep understanding of Chicago’s place as an architectural mecca, take the Chicago Architecture Foundation boat tour on the Chicago River. Kids love seeing the city from the river — and seeing the underside of the bridges over the river.
Visit Lincoln Park Zoo. One of the last free zoos in the USA, this lakefront gem has a children’s zoo, a lagoon where you can rent peddle boats and beautiful landscaped gardens. Don’t miss a stop at the Lincoln Park Conservatory on your way out of the zoo.
Eat. In Chicago, that means deep dish pizza or a Chicago hot dog. Just remember: No one over age 18 orders catsup on a hot dog in Chicago. If you do, everyone will know you’re an out-of-towner. Here are our favorite kid-friendly restaurants in Chicago.
TravelingMom Tip: One of our favorite things to do when taking a vacation is to hire a photographer for family photos. This is a special gift and souvenir that we cherish. We use Flytographer to book a local photographer located in the area that we're traveling to. Use this link and you will get $25 off your photo session.
Oak Park, Illinois
Best known as the home of Frank Lloyd Wright, Oak Park is the first suburb west of Chicago and easy to get to via the Green Line on Chicago’s famous elevated train system. (It seems like just about every movie filmed in Chicago has at least one scene that takes place beneath the L tracks!)
Stop at the Frank Lloyd Wright Home and Studio, then take the walking tour of the Wright-designed homes in the surrounding neighborhood.
Great River Road Scenic Byway
More than 2,000 miles long, the Great River Road Scenic Byway runs along the Mississippi River through 10 states and hundreds of historic river towns.
That includes 33 miles from Hartford to Grafton, Illinois, where the road is known as the Meeting of the Great Rivers National Scenic Byway. This drive is particularly beautiful in the fall when the trees turn vibrant shades of red, orange and yellow.
Starved Rock State Park
This lovely state park is about 90 minutes west of Chicago. It’s a mecca for hikers and nature lovers. Trails wind along the gorgeous steep sandstone cliffs that line the Illinois River.
During the spring and early summer, it’s easy to find waterfalls along the hiking trails. You can camp there or spring for a stay at the Starved Rock Lodge.
Midwest Road Trip: Indiana Destinations
Indiana Dunes National Park
The stunning sand dunes that line the southern tip of Lake Michigan were designated the USA’s 61st national park in February 2019. Indiana Dunes has 15 miles of stunning beaches and huge dunes to climb.
The sand dunes and beautiful blue water look like something you’d see on the east coast – not something you’d find on a Midwest vacation, When you’re done playing on the beach, swimming, and going horseback riding, there are lots of craft breweries and local restaurants nearby.
This Midwest town is one of our favorites. It’s small enough to feel manageable, even to people who aren’t used to urban hustle and bustle, but big enough to offer plenty of fun.
Start at Indianapolis’ White River State Park. Located right in the center of the city, it’s home to the Indianapolis Zoo, a minor league baseball stadium, the Eiteljorg Museum of American Indians and Western Art, the Indiana State Museum and the NCAA Headquarters and Hall of Champions, with lots of fun hands-on play for tweens and teens.
Indianapolis is also home our fave kids’ museum, the Indianapolis Children’s Museum, one of the world’s biggest and best. The city neighborhoods of this Midwest vacation spot are connected via biking trails that wind through its cultural districts.
TravelingMom Tip: If you have a membership to a local museum or zoo, check to see whether it is a member of a reciprocity group before you head off on your family vacation. It could mean free entrance to museums and zoos during your trip as well! There are groups for science museums, zoos and cultural institutions.
Santa Claus, Indiana / Holiday World
Who doesn’t love an entire theme park themed to Christmas?
Midwest Road Trip: Iowa Destinations
TravelingMom Nasreen Stump hit several cool Iowa spots on her journey across the Midwest and says she wishes she had planned more time there. From unique road side stops to outdoor fun that allows kids to be kids Iowa had it all.
Let the kids run off some road trip energy at Des Moines Pappajohn Sculpture Park. This park is located off of Grand Avenue and showcases more than 25 sculptures spread over more than 4 acres. Metered parking is readily available nearby.
Not only is this a great photo spot that teens will love for the Insta, but it’s got a hill in it that Nasreen’s kids rolled down over and over. Who said fun can’t be free!?
TravelingMom Tip: For the best parental experience, grab a coffee down the street at Zanzibar’s Coffee Adventure. Then enjoy it at the sculpture park while your kids amuse themselves.
Located where Wisconsin, Illinois and Iowa meet, Dubuque is perfectly located for a Midwest road trip- especially if you want to hit more than one state!
While there is plenty to do in Dubuque including an arboretum, aquarium and caves to explore, we highly recommend checking out the Fenelon Place Elevator (also called the Fourth Street Elevator). Technically a funicular, this elevator has been called the shortest, steepest scenic railway ride. You sit in a cable car for the ascent. Once you’re at the top, you’ll have a spectacular view of the Mississippi River and three states.
There is a small fee based on age which can you find here. Nasreen’s kids loved the story behind how it was built. It includes a wealthy man with a love of naps, which gave her and the kids a chuckle.
How often do you have the opportunity to feel like you’re visiting another country without leaving the Midwest? Elk Horn, Iowa, is home to the Museum of Danish America.
If you have older kids they’ll enjoy roaming the grounds and exploring the museum. For kids under 12, the better stop is going to be the Danish Windmill. You’ll get some fun family photos and get to check out a working windmill. Originally built in Nørre Snede, Denmark in 1848, the windmill was brought to the United States in pieces and rebuilt by a team of volunteers in 1976.
The site also has a village replica, tiny chapel and gift shop full of fun items and things to eat. Head on to Kimballton (5 minutes away) next.
You may never have heard of tiny Kimballton. Iowa. but this town of fewer than 500 people is another great stop to explore Danish heritage in Iowa.
Kimballton is home to Hans Christian Andersen’s The Little Mermaid & Sculpture Gardens. This small park based around a fountain features a replica of the Little Mermaid statue in Copenhagen, Denmark. There are 8 more bronze sculptures representing stories by Andersen. Nasreen’s kids loved seeing these and talking about the original stories they were based on. It’s a good, quick stop for the whole family.
TravelingMom Tip: There’s a small playground nearby so be ready for the kids to ask to play.
The Quad Cities include Bettendorf and Davenport in Iowa and Moline and Rock Island in Illinois. Rent a bike and ride the path along the Mississippi River.
Tractor-loving kids will require a visit to the free John Deere Pavilion in Moline. The Putnam Science Museum in Davenport is also a must-do. The whole family will demand home-made ice cream from Lagomarcino’s. Choose to stop at the downtown location, open since 1908.
Midwest Road Trip: Kansas Destinations
Kansas City, Kansas
The College Basketball Experience in Kansas City is a slam dunk for families.
But our favorite thing to do in KC is the National Museum of Toys and Miniatures where it’s virtually guaranteed you’ll hear someone say, “Oh, I used to have that toy!”
Midwest Road Trip: Michigan Destinations
Whether you’re visiting gorgeous beach towns on Lake Huron, spending the winter with sled dogs in Traverse City, or touring the State capitol in Lansing, there are so many delightful towns to visit in both the lower and upper peninsulas of Michigan. The state also offers a few unique Midwest vacation spots for your Midwest road trip.
TravelingMom Tip: Looking to visit both Wisconsin and Michigan in one trip? Make the travel more fun by crossing Lake Michigan on the SS Badger car ferry!
If you haven’t been to Detroit lately, you haven’t been to Detroit. It is a city on the rise. Plan to spend a day at the beautiful Belle Isle Park, home to one of the oldest aquariums in North America. It’s small and free and well worth a look to show the kids how aquariums have changed over the years.
The Detroit Historical Society, a small but exceedingly well done museum, showcases the history of the town the automakers built. The Detroit Art Institute across the street is a world-class museum with impressive special events.
And don’t miss a chance to eat a burger and fries at Hop Cat!
Holland, Michigan may be the closest thing you can get to the Netherlands without traveling to Europe.
A large, authentic Dutch windmill is perhaps the highlight of a stop in this Midwest vacation spot but there also are Dutch restaurants, architecture tours, and even wooden shoe carving shows. If you visit in May, you’ll be treated to the Tulip Time Festival, too!
Mackinac Island, Michigan
This no-cars-allowed island between Michigan’s upper and lower peninsulas is probably the most famous Midwest vacation spot on our list.
Mackinac Island is home to the United States’ second-ever National Park. Mackinac Island National Park is 70 acres of forests, incredible rock formations, wildlife, and beautiful water features, as well as historical and cultural landmarks. And it’s a wonderful place to explore on bicycles because you don’t have to dodge cars!
Before you go, practice saying the name. It’s pronounced Mack-i-naw even though it’s spelled Mackinac. And it’s definitely worth a visit, even if you can only spend one day on Mackinac Island.
Long the playground of wealthy Chicagoans looking to beat the city heat each summer, there is a wealth of fun outdoors things to do in Saugatuck and neighboring Douglas. Topping that list is a visit to Oval Beach, one of the most beautiful beaches on Lake Michigan.
It’s no wonder this small town was named the “Best Beach Town in the Midwest” for 2021 by Midwest Living magazine.
Midwest Road Trip: Minnesota Destinations
Duluth, like many of the Great Lakes towns on this Midwest vacation list, offers lots of outdoor activities for families. It is also home to Great Lakes Aquarium, the only freshwater aquarium in the US.
And, yes, it’s even fun to visit Duluth in winter.
Home to the Mall of America (which may be reason enough to visit), Minneapolis and its sister city, St. Paul, have so much to offer visitors. Explore the largest mall in the US, or enjoy a number of theater performances.
Hike to Minnehaha Falls or explore miles of nature trails along the Mississippi River. It’s also a super affordable Midwest vacation spot, with lots of free things to do with kids.
Midwest Road Trip: Missouri Destinations
Branson, Missouri, is a fun and affordable vacation destination with beautiful lakes and mountains as well as fun shows and theme parks.
Silver Dollar City is a family-friendly park themed to an old mining town. Choose from more than 40 rides and live entertainment.
Lake of the Ozarks, Missouri
“The Strip” at Lake of the Ozarks offers your typical tourist fare: gift shops, arts and crafts, fudge and candy factories, and the like. But it’s the beautiful lake (with more than 50 marinas), a collection of golf courses, horseback trails, boat tours through caverns, and tours of mansions (both current and historic) that makes this a worthy Midwest vacation spot that will keep you busy for as long as you want to stay.
St. Louis, Missouri
St. Louis is one of our favorite getaway spots. Less than 6 hours from Cincinnati, Chicago, Indianapolis, Kansas City, Des Moines, Milwaukee, Louisville, Nashville, Tulsa, and Memphis, it may be the most centrally located destination on this list.
You’ll want to visit the Gateway Arch, of course, but plan to spend some time at Forest Park. It’s larger than New York’s Central Park and home to a free zoo and a number of free museums. There’s also the Anheuser-Busch Brewery and Grant’s Farm, and the eclectic, one-of-a-kind City Museum.
There’s a really fun and trendy waterfront area (Laclede’s Landing), plus a brand new aquarium and lots of stuff for sports lovers, including taking in a Cardinals game at Busch Stadium.
St. Charles, Missouri
Just a half hour’s drive from St. Louis is charming and historic St. Charles.
Celebrate car culture with a stop at Fast Lane Classic Cars to ogle the 200 classic and muscle cars on display. Or forget about your car for a while and hop on board the St. Charles Trolley to ride the 30 minute loop around town. Download the app to track where the trolley is so you’ll know how long you’ll need to wait for a ride. The best part? It’s free!
Midwest Road Trip: Nebraska Destinations
Omaha as a must-do for foodies. It is one of the nicest, cleanest, and most hospitable Midwest vacation spots – especially in the spring when the weather is perfect.
Don’t miss the opportunity in Omaha for your kids to stand in two states at once! Even though it was pouring rain. TravelingMom Nasreen Stump said her kiddos still thought it was one of the coolest things they did on their Midwest road trip.
There is plenty of parking on the Omaha side of the Bob Kerrey Pedestrian Bridge. You can walk to the middle of the bridge and straddle the state line between Nebraska and Iowa. Activities for kids exist on both sides of the bridge.
Midwest Road Trip: Ohio Destinations
Like the other large cities on this list, Cincinnati offers far too many attractions to really cover here. World-class museums, one of the best zoos in the country (you can even camp with the giraffes!), several professional sports teams, and a vast history are only a handful of the reasons to visit the Queen City.
The most famous attraction in Cleveland, Ohio is probably the Rock and Roll Hall of Fame and Museum. Even my kids, who didn’t know half of the artists, found plenty of interesting things to see and do.
Don’t miss a stop at the fun hands-on Great Lakes Science Center next door. Save a few bucks by buying the combo ticket admission to both the hall of fame and science center.
While you’re in Cleveland, you should also check out the beautifully revitalized Little Italy neighborhood or catch a Cavaliers game.
Hocking Hills, Ohio
Travel less than an hour from Columbus, Ohio’s capital city, and you’ll find yourself at the beginning of Appalachia.
Hocking Hills State Park has some of the area’s best hiking for families. We’ve taken young kids there on paved trails and spent time on more difficult hikes with older kids and adults. For adventure seekers, there’s zip lining.
This Midwest vacation spot is also home to caves, waterfalls, and cultural and historic attractions. Small lakes offer boating (pontoon and human-powered craft such as kayaks or canoes only) and water sports.
Sandusky/Lake Erie Shore, Ohio
Sandusky, Ohio, is home to Cedar Point, which bills itself at the Roller Coaster Capital of the World. We agree. It’s where we took our kids to teach them to love roller coasters! Start with the smaller, tamer coasters and work your way up the Top Thrill Dragster — a steel coaster that reaches speeds of 120 mph as it shoots you straight up, then crawls over the top to wind straight back down, all in 17 seconds.
There are also four indoor waterpark resorts and beautiful beaches along Lake Erie. From Sandusky, take a ferry to Kelleys Island or South Bass Island’s Put-in-Bay. On these Lake Erie islands, take a cave tour, go fishing, or climb the Marblehead Lighthouse in Port Clinton for spectacular views.
Warren County, Ohio
You can also take a scenic train ride to Lebanon, the county seat of Warren County – “Ohio’s Largest Playground.” Here you’ll find a charming downtown area with some of the country’s best antiques shopping.
You can even dine – or stay overnight – at the Historic Golden Lamb Inn & Restaurant. Opened in 1803, the Golden Lamb has hosted 12 US presidents and dozens of other US and world dignitaries.
Midwest Road Trip: South Dakota Destinations
Driving through South Dakota is THE iconic Midwest road trip. Start with a stop in Wall, South Dakota, to gawk at the incredibly touristy Wall Drug, wind through the breathtaking Badlands National Park, see Mount Rushmore and the Black Hills, pay your respects to Crazy Horse, then watch the buffalo roam at Custer State Park.
The Corn Palace
This kitschy stop is in Mitchell and it’s a must-do if you’re traveling I-90 across Iowa. It’s been operating since 1892 and is exactly what it sounds like: a reason to get people to pull off the highway and visit Mitchell. Every year, artists decorate the outside of the building with 325,000 ears of corn.
A visit is free, but bring your wallet. The kids will want to buy some of the corn-y souvenirs and treats.
Badlands National Park
Take the Badlands Loop Road (Highway 240) and stop often to ogle the Instagrammable rock formations, steep canyons and towering spires of Badlands National Park. Watch for bison, bighorn sheep, prairie dogs and other protected wildlife.
Look up President Washington’s nose (really!) as you hike around Mount Rushmore. That’s the national park where the busts of four presidents — George Washington, Thomas Jefferson, Theodore Roosevelt and Abraham Lincoln — are carved into the side of the Black Hills Mountains. This Midwest vacation spot draws more than 3 million visitors every year.
You can hike, fish and be wowed by Needles Highway here. But the biggest reason to visit Custer State Park is the chance to stop the car and watch the herd of 1,300 grazing buffalo on the Wildlife Loop.
Unlike the other South Dakota attractions, Crazy Horse is a private endeavor run by a nonprofit. The project was started by Korczak Ziolkowski in 1948. It’s still far from finished.
Read More: Fun things to do in Chattanooga Tennessee with kids.
Midwest Road Trip: Wisconsin Destinations
Madison is the capital of Wisconsin and it’s a rockin’ college town. Take the free tour of the beautiful capital building, then walk across the street to browse through the (also free) Wisconsin Veterans Museum.
On Saturdays from April to November, the capital is circled with a huge farmers’ market selling everything from veggies to the must-try Wisconsin cheese curds. (You know they’re fresh if they squeak when you bite into them.)
We have a full post on fun, free things to do in Madison with families that will help you plan your trip.
Milwaukee, Wisconsin combines a beautiful beach on Lake Michigan with the hustle and bustle of an urban center. Visit the world-class Milwaukee Art Museum and take the little ones across the street to the Betty Brinn Children’s Museum and school-age kids to Discovery World.
Motorcycle fans can visit the Harley-Davidson Museum, and visitors can take part in several festivals throughout the year – including Summerfest, one of the world’s largest music festivals.
Elkhart Lake, Wisconsin
About an hour north of Milwaukee, Elkhart Lake is a lovely, serene spot. Several hotels nestle along the shores of the lake, where the calm water tends to be much warmer than Lake Michigan. We love the beautiful Osthoff Resort which has a number of wonderful restaurants. Race fans will want to plan a visit to Race America to watch a race or take a track driving course.
Green Bay, Wisconsin
Green Bay is best known as the home of the powerhouse Green Bay Packers football team, which is celebrated at the new Titletown complex.
But Green Bay also is the gateway to Door County. Known as the Cape Cod of the Midwest, Door County is famous for its small towns along the bay and its fish boils.
Wisconsin Dells calls itself the “water park capital of the world.” While we love the giant indoor Kalahari Waterpark any time and the giant outdoor Noah’s Ark waterpark in the summertime, there’s much more to do there than just water slides.
Much like a visit to Branson, Missouri, or Gatlinburg, Tennessee, you’ll find a plethora of go-kart tracks, live dinner shows and boat tours. Don’t miss a ride on the famous Duck Boats! Away from the hustle and bustle of those tourist destinations though, you’ll also find plenty of water sports and hiking in the Dells’ three nearby state parks. Learn more about Wisconsin Dells and five of the water parks on our full article comparing them.
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So whether you live in the Midwest and are looking for quick and easy (and perhaps off-the-beaten-path) destinations, or are traveling to visit an iconic Midwest vacation spot, be sure to check out these TravelingMom approved destinations as you plan your Midwest road trip.