The Best Road Trips In Midwest America You Need To Take

When it comes to the Midwest, there is no better way to see it than from the driver’s seat. From geographical variety to unique pit stops, there is no place better to explore. Just be sure to have the right tires if winter is coming.

1. Louisville to Indianapolis

Hotel

This trip is a fascinating one that spans from metropolis to metropolis, with little but farmland in between. However, this farmland is completely picture perfect. While the drive only lasts a tad under two hours, you can always stop off in Bloomington for some good old college fun at Indiana University or simply take the long route through West Baden Springs, and check out the West Baden Springs Hotel, which looks more like a swanky European theater than a hotel in rural Indiana.

Best time to go: October–February

Louisville to Indianapolis Route

West Baden Springs Hotel | © Sarah Poole / Flickr

2. Chicago to Milwaukee

This road trip is not only laid-back, but it’s also a daily commute for some Midwesterners! But the drive is made so much quicker by uninterrupted views of the beautiful Lake Michigan. Driving along highways in Chicago is also a complete experience—the drivers there are aggressive, and it’s incredibly fun to try and keep up with traffic. Along the way are some amazing and hilarious attractions, such as the Jelly Belly Warehouse Tour and the unforgettable Mars Cheese Castle, which is a castle full of the world’s best cheese.

Best time to go: March–November

Chicago to Milwaukee Route

Mars Cheese Castle | © bradhoc / Flickr

3. Milwaukee to Des Moines

For the most variety of landscapes, you’ll want to drive from Milwaukee to Des Moines. Milwaukee is a deceptive town, as it sports both a hilly terrain as well as sprawling beaches; Des Moines, on the other hand, is flat with gorgeous plains surrounding it. The drive to get there really could go two ways. The first will take you through the die-hard college towns of Madison, Wisconsin, which represents the University of Wisconsin-Madison, as well as Iowa City, Iowa, which supports The University of Iowa. Both cities are guaranteed to provide an excellent time. If scenic views are more important, then take the route through Rockford, Illinois, especially if it’s in the fall when the leaves are changing color. The views are unlike any other.

Best time to go: June–October

Milwaukee to Des Moines Route

Majestic Theatre and Wisconsin State Capitol | © Paul Frederickson / Flickr

5. Ann Arbor to Minneapolis

This road trip is excellent for those with the west in their hearts! The drive through Michigan is varied with both cities and country, and this trip will go through Kalamazoo, which showcases some of the best nature in Michigan. It also passes through Chicago, as well as Eau Claire, Wisconsin, which is a hidden gem of the cheese state. St. Paul is another fascinating place to stop off; it has lots of restaurants and nightlife. Make sure to stop by the Spoonbridge and Cherry 1985–1988 in the Minneapolis Sculpture Garden for the best Instagram moments. Minneapolis is a town to bring your swimsuits to; after all, there are lakes all around in Minnesota!

Best time to go: July–October

Ann Arbor to Minneapolis Route

Spoonbridge | © Justin Ladia / Flickr

Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.

Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.

We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.