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Best of the Midwest road trip
Land at O’Hare International Airport, collect your Hertz car rental and head out into Chicago with the excitement that your Midwest road trip adventure has just begun. Take in the sights and sounds of the Windy City before hitting the road and discovering highways that stretch out with natural, scenic views on either side.
We explore the best of the Midwest towards South Dakota, highlighting key Midwest landmarks and travel advice along the way. Reserve your Hertz car rental and get the freedom to explore at your own pace, discovering Midwest culture, summer road trips and much more.
Summary
- A multi-state road trip connecting Chicago to South Dakota's Badlands via St. Louis, the Ozarks, Kansas City and the Great Plains
- Experience scenic drives, outdoor adventures and small-town charm across five different states
- Designed for flexible, explorative travel with a reliable car rental to discover the Midwest at your own pace.
The drive from Chicago (Illinois) to Badlands & Black Hills (South Dakota)
The southern loop from Chicago to the Badlands stretches over 1,800 miles and is best taken over a week or more to enjoy it properly. The route weaves through Illinois, Missouri, Kansas, Iowa and Nebraska, using a mix of major highways and quieter regional roads.
You’ll still spend time on interstates like I‑55 and I‑70, but these are broken up by more scenic stretches and city stops. There are some tolls when leaving Chicago, though most of the journey is toll-free. However, the shift in scenery and pace makes the drive feel rewarding from start to finish.
Starting point: Chicago
Every road trip needs a strong starting point, and Chicago sets the tone effortlessly. Before heading out, spend time at Millennium Park, home to Cloud Gate, where the skyline reflects across its mirrored surface and draws visitors year-round. Just a short walk away, the shoreline of Lake Michigan offers wide paths and open views across one of the largest freshwater lakes in the world.
A short stop here offers a great introduction to Midwest culture before you set off. For the journey ahead, you ideally want to have a midsize SUV that provides comfort and plenty of room for longer stretches on the road.
Stop 1: St. Louis, Missouri
About five hours south of Chicago, along I‑55 to Missouri, St. Louis begins to reveal itself before you fully arrive. The Gateway Arch rises above the skyline, its curved steel frame catching the light and marking your arrival into the city. It is worth stopping to see up close, both for its scale and its calm setting along the Mississippi River.
From there, head to the Delmar Loop, home to the St. Louis Walk of Fame. Along the pavement, bronze stars honor over 150 notable figures connected to the city, including Maya Angelou, Chuck Berry and Miles Davis. The Loop itself is lively, with independent shops, restaurants, and live music venues that give the city its energy. It’s an ideal place to spend a few hours before continuing south.
Stop 2: Branson & the Ozarks, Missouri
Leaving St. Louis behind, the drive south begins to shift in tone as flat farmland gradually gives way to the rolling, wooded hills of the Missouri Ozarks. It’s a noticeable change and one that signals a slower, more relaxed pace for this part of the journey.
Table Rock State Park sits along the edge of Table Rock Lake, where clear water and long stretches of shoreline create an easy setting to spend time outdoors. The marina offers boat and kayak rentals, while lakeside trails provide a quieter way to take in the surroundings. It is the kind of place where you can easily lose track of time appreciating Mother Nature.
Nearby lies Silver Rock City, combining rides, craft demonstrations and live shows in a setting inspired by an 1880s mining town. Together, Branson’s outdoor activities make it a stop worth extending.
Stop 3: Kansas City, Missouri
Arriving from the Ozarks, Kansas City feels like a return to city energy, though with a character entirely its own. Known as the City of Fountains with nearly as many as that of Rome, you’re invited to explore its deep-rooted jazz heritage and celebrated food scene. Alongside a range of other Kansas City attractions, this quickly becomes one of the most distinctive stops on the route.
Start at the National WWI Museum and Memorial, set beneath the Liberty Tower. Its carefully curated exhibits and panoramic views offer both context and perspective, making it one of the most memorable cultural stops on the trip. From there, head to City Market, especially earlier in the day, where local vendors, cafés and fresh produce create a laidback yet lively atmosphere.
As evening approaches, the Power and Light District becomes the center of activity, with joints featuring live music all within walking distance.
Stop 4: Des Moines, Iowa
Leaving Kansas City behind, the drive into Iowa feels quieter, but Des Moines quickly proves to be one of the Midwest’s hidden gems. This stop centers on the Des Moines Art Center, a place that stands out before you even step inside. Its three interconnected buildings were designed by Eliel Saarinen, I.M. Pei and Richard Meier, each reflecting a different architectural style while still working together as a whole.
Inside, the collection includes works by major artists such as Georgia O’Keeffe and Edward Hopper, alongside rotating exhibitions that keep the space feeling modern. Admission is free, though it is worth noting that the gallery is closed on Mondays.
Nearby, the Downtown Sculpture Park extends the experience outdoors, with large-scale installations set across open green space. And when night falls, the city’s growing dining and arts scene offers plenty of reasons to stay late into the night.
Stop 5: Riverside, Iowa
Continuing along I‑80, a short detour brings you to one of the most unexpected stops on the entire trip. Riverside, Iowa, proudly claims to be the future birthplace of Star Trek’s Captain James T. Kirk, a title officially adopted in the 1980s and embraced ever since.
Near City Hall, a bronze statue of Kirk stands as the town’s centerpiece, while an adjacent monument marks the site of his future birth. The Voyage Home Museum, run by local volunteers, houses a detailed collection of Star Trek memorabilia that draws fans from across the country. Even the main street reflects the theme, with banners and small nods to the series throughout. It is an unusual stop for a Midwest road trip, but an enjoyable and light-hearted one nonetheless.
Stop 6: Omaha, Nebraska
Crossing into Nebraska, Omaha arrives with some fanfare, proving it deserves your time. The Durham Museum, for example, is set inside a beautifully restored Art Deco train station. It focuses on the history of the American West, with immersive exhibits and vintage train cars that bring the region’s past to life.
The building itself is part of the experience, with marble floors and grand hallways that reflect a different era. It is an easy place to spend a few hours and adds depth to your visit beyond the city’s more well-known attractions. In the evening, the Old Market District offers a change of pace, with Bohemian restaurants creating a relaxed atmosphere to end the day.
Finish point: Custer State Park & Badlands National Park, South Dakota
The final stretch into South Dakota feels like a gradual shift from city to wildlife territory. As you move west of the Missouri River, the landscape breaks apart into the layered rock formations of Badlands National Park, where pink, grey and rust tones catch the light throughout the day.
Before reaching the park, Custer State Park offers an equally memorable detour. Needles Highway meanders through granite spires and narrow tunnels, while Wildlife Loop Road gives you a chance to see bison moving freely across open land.
Together, these stops create a natural ending point for your Midwest road trip, where the scale of the landscape and the abundant wildlife prove a noteworthy epilogue to an exciting adventure.
Best of the Midwest road trip, let’s go!
A Midwest road trip unfolds gradually, shifting from busy city streets to wide open landscapes before you realize just how much ground you’ve covered. It’s the freedom to pause and reflect when something catches your eye and continue when you’re ready that makes the experience so memorable. And this is only possible behind the wheel of a car rental.
Reserve with Hertz today, and move between destinations at your pace while enjoying the best of what the Midwest has to offer.
FAQs
How long does a Midwest road trip take?
The full route described here should take about 8 to 10 days, depending on how long you spend at each stop. The most common mistake is underestimating how long you'll want to stay somewhere. Some places naturally invite you to stay longer, particularly Kansas City and St. Louis, so it is worth factoring in a few hours or days for detouring.
What is the best time for a Midwest road trip?
The best time for a Midwest road trip is from late May through early October, when weather conditions are generally mild and most attractions are open. It’s worth noting that Needles Highway in Custer State Park, South Dakota, is typically only accessible between April and October, so timing is important.
Is a car necessary for exploring the Midwest?
For a route like this, a car is essential. The landscapes, national parks, and key stops are spread across multiple states, often far from major transport links. While some cities are accessible on their own, it is the drive between them that defines the experience and makes the journey worthwhile.
How does this road trip differ from the northern loop?
The northern loop focuses on water bodies, forests and charming lakeside towns. This southern loop is about cities, culture, the Ozarks, and the wide-open plains, two very different Midwest experiences. However, both finish at the same spectacular place: the Badlands. Combined, they make up one of the great American road trips.
