Louisville to Indianapolis
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
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
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
Kentucky to the “UP”
This trip has everything. This ultimate Midwest tour will hit nearly every desirable city, from Indianapolis to Chicago and Milwaukee, making this excursion perfect for seeing everything that the Midwest has to offer. It also hits some lesser-loved cities such as Lafayette, Indiana; Evanston, Illinois; and Green Bay, Wisconsin. When the cities drop off, all that’s left are the picture-perfect pines of the north woods. The Upper Peninsula is the unsung hero of the Midwest, so make sure to spend some time exploring and conversing with the local “Yoopers.” Just make sure to go sometime in the summer because it’s been known to snow as early as October and as late as May in Michigan.
Best time to go: June–September
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