are you ready to explore the heart of America?
The Midwest is the heartland of the United States. Stretching across states like Illinois, Indiana, Iowa, Kansas, Michigan, Minnesota, Missouri, Missouri, Nebraska, North Dakota, Ohio, South Dakota and Wisconsin, it’s a diverse region made for adventure. Whether you’re an urbanite looking for city sophistication, a wilderness getaway, small town Americana or just a lover of the open road, the Midwest is perfect for exploring.
Cheaper Than Cars makes it easy to find the right vehicle for a great Midwest getaway. With pickups throughout the region, from Chicago to Minneapolis, Detroit to Milwaukee, we‘ve got the Midwest covered.
Here are ten of the best Midwest road trips to whet your appetite
Great Lakes Adventure
Beginning in Chicago and traveling through the states of Illinois, Indiana, Michigan and Wisconsin, The Great Lakes Adventure is a journey through the heart of the Midwest. Leaving the Windy City behind, the route heads along the shores of Lake Michigan. Traversing the sandy beach of Indiana Dunes National Park, it eventually reaches Detroit, where roadtrippers can learn more about the city’s automotive and Motow heritage. Heading north, the route passes through charming towns such as Traverse City and Petoskey, with their cherry orchards, vineyards and panoramic views of Lake Michigan.
Continuing through the Upper Peninsula, the road trip can include stops at Pictured Rocks National Lakeshore, Tahquamenon Falls and the historic maritime town of Sault Ste. Marie. Heading south, travelers can explore the revitalized city of Milwaukee, with its breweries, museums and lakeside activities. This epic Great Lakes adventure concludes in the beautiful lakeside city of Madison.
- Total driving distance: 2,123 km
- Driving time: 20-25 hours
Tour of the Mississippi River Valley
Beginning in Minneapolis and traveling through the states of Minnesota, Iowa and Missouri, the Mississippi River Valley tour combines dense forests, serene lakes and charming cities. Travelers can begin their adventure by exploring Twin Cities landmarks, from the modern art installations of the Minneapolis Sculpture Garden to the historic architecture of the Stone Arch Bridge. Leaving Minneapolis, the road trip follows the meandering course of the Mississippi River.
Entering Iowa, the tour may include stops in Dubuque, with its well-preserved architecture and riverside charm. From there, the journey continues through quaint riverside towns, such as the lively riverfront of Davenport and the unique history of Nauvoo, Illinois. As the journey progresses into Missouri, the iconic Gateway Arch in St. Louis welcomes travelers. To the south, the river becomes the backdrop of picturesque limestone cliffs of the Ozark Mountains. Explore river towns like Cape Girardeau and the historic charm of Hannibal, Mark Twain’s hometown.
- Total driving distance: 800 miles (1,287 km)
- Travel time: 12 hours
Kansas Flint Hills
The Kansas Flint Hills Scenic Byway takes you on a captivating road trip through one of the last remaining high prairie ecosystems in the world. Approximately 47 miles long, mostly along Kansas Highway 177, the byway seems far removed from the hustle and bustle of urban life.
The Flint Hills are prized in the Midwest for their rolling terrain and are characterized by steep slopes and limestone outcroppings. Topped by tall grasses, the hills seem to sway in the wind. The Tallgrass Prairie National Preserve, located near the highway, offers the opportunity to explore the prairie up close, with guided tours and hiking trails that provide insight into the natural and cultural history of the region.
Beginning in Strong City and ending in Cassoday, this gentle road trip is the perfect retreat from urban life.
- Total driving distance: 76 km (47 miles)
- Driving time: 1.5 hours
Detroit to Mackinac Island
Combining urban charm with the peaceful serenity of the Great Lakes, this classic Midwestern road trip takes you from the heart of the Motor City to the shores of Lake Huron. Before leaving Detroit, travelers can learn more about the man who invented modern motoring at the Henry Ford Museum. Heading north, the road trip turns toward the Straits of Mackinac, where the scenic Mackinac Bridge connects Michigan’s upper and lower peninsulas. The bridge itself offers breathtaking views of Lake Huron and Lake Michigan.
Upon arriving in Mackinaw City, travelers must leave the car behind and board a ferry to Mackinac Island, where no motorized vehicles are allowed. Characterized by its Victorian architecture, horse-drawn carriages and tranquil atmosphere, the island is steeped in natural beauty. With Mackinac Island State Park at its center, there are countless trails to explore.
- Total driving distance: 450 km (280 miles)
- Travel time: 5.5 hours
Badlands and Black Hills
Departing and arriving in Rapid City, South Dakota, this trip through the Badlands and Black Hills is a journey through a land of striking natural contrasts and rich cultural history. Beginning with the rugged beauty of Badlands National Park, the landscape combines canyons, spires and vast prairies. Overlooks allow for sightings of a variety of wildlife, including bison and prairie dogs.
Heading west toward the pine-covered Black Hills, you reach Mount Rushmore, famous throughout the world for the monumental sculpted faces of the great American presidents of the past. Continuing through Custer State Park, the wildlife loop offers encounters with herds of bison and other native species. The road winds between the granite spires of Needles Highway, leading to serene Sylvan Lake. The journey culminates at the colossal Crazy Horse monument, a tribute to Native American culture.
- Total driving distance: 60 miles (97 km)
- Driving time: 2 hours
Scenic drive from Minneapolis to Duluth
This scenic route through the heart of Minnesota offers diverse landscapes, charming river towns and historic sites. Leaving Minneapolis, the scenic route heads northeast toward Duluth, following the course of the Great River Road along the mighty Mississippi River. Along the way, historic sites and scenic overlooks offer a glimpse of the region’s cultural and natural heritage.
As you approach Duluth, the landscape transforms into the rugged beauty of Lake Superior, the largest of the Great Lakes. Perched on the western end of Lake Superior, Duluth has a maritime charm that is great to explore. The Great Lakes Aquarium will give you an insight into the aquatic life of the lake. Continuing onward, the North Shore Scenic Byway, which stretches from Duluth to Grand Portage, offers stunning views of Lake Superior’s rocky shoreline, pristine forests and the iconic Split Rock Lighthouse. This classic among Midwestern road trips allows detours to state parks, waterfalls and charming little towns along the way.
- Total driving distance: 450 miles
- Driving time: 9 hours
Missouri Bourbon Route
Although bourbon is most readily associated with Kentucky, Missouri has its own distilling tradition that rivals that of its neighbor. The Missouri Bourbon Trail takes you on a journey through a selection of craft distilleries, each offering a different take on the art of bourbon making. Combining historic charm with modern innovation, visitors can explore the region’s rich heritage while savoring handcrafted bourbons that reflect the creativity of the state’s distillers.
Distilleries often offer guided tours explaining the bourbon-making process from grain to bottle, and tasting rooms offer the opportunity to sample a variety of bourbons. The Missouri Bourbon Trail is not just a trip for bourbon connoisseurs, there are many great places to eat and drink, small towns to explore and historic attractions along the way.
- Total driving distance: 483 km
- Travel time: 7 hours
From Omaha to Scotts Bluff National Monument
Omaha has experienced a renaissance as a Midwestern music center.
Known for its vibrant indie scene, the city is a hub for underground artists and nationally known bands. Before leaving the city, travelers can explore the Old Market District or visit the Henry Doorly Zoo. Heading west from the city, this Midwest road trip traverses the expansive prairies and farmlands that define much of Nebraska’s heartland.
Scott’s Bludd National Monument rises dramatically above the North Platte River Valley, and its towering bluffs served as a landmark for pioneers traveling the Oregon Trail in the 19th century. Today, you can learn more about those pioneers at the visitor center, or hike trails that lead to panoramic views from the summit.
- Total driving distance: 420 miles (676 km)
- Travel time: 7 hours
Travel to Wisconsin Northwoods
Wisconsin’s northern region is made up of dense forests, pristine lakes and charming small towns. Beginning in Minocqua, a quintessential Northwoods town surrounded by a chain of lakes, the journey takes you along winding roads shaded by towering pines. Heading south, the drive will take you to Eagle River, a Northwoods gem known for its chain of 28 lakes. The town has a charming main street and is a center for water sports.
Continuing the journey, Rhinelander exudes small-town charm. With local stores and restaurants, you can also get up close to the statue of the Hodag, a mythical creature that has become a symbol of the region.
The Wisconsin Northwoods Drives, which includes stretches of Wisconsin’s Rustic Roads and the Great Divide National Highway, is a classic Midwestern road trip for leisurely enjoyment.
- Total driving distance: 150 miles (241 km)
- Driving time: 4 hours
Illinois River Highway
The Illinois River Road is a designated route, starting in Ottawa and heading south to Havana, IL. This journey through the heart of Illinois, with beautiful natural scenery, charming small towns and a rich industrial heritage, is an out-of-the-ordinary adventure. Known for its towering sandstone cliffs, lush forests and waterfalls, Starved Rock State Park offers hiking trails with panoramic views of the Illinois River and surrounding landscapes.
As the journey continues south, the towns of LaSalle, Peru and Spring Valley offer the opportunity to explore the region’s rich history, from the Hegeler Carus Mansion to the coal mining heritage on display at the Hall Township Coal Mining Museum. This route is characterized by small American towns, such as Henry and Peoria, which offer riverside stops along the way. Concluding in the quiet town of Havana, with its historic architecture and riverside parks, the Illinois River Road is a relaxing journey into the heart of the Midwest.
ready for your Midwest adventure?
It’s often overlooked, but the American Midwest is the perfect playground for road trip adventurers. With so many fascinating cities, its cultural diversity and breathtaking scenery, the Midwest is the best way to discover the lesser-known America.
Cheaper Than Cars makes it easy to find the right car for your Midwest road trips, whatever your budget.
