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The Best Midwest Road Trip Itinerary for Summer 2023

Young lady stands with Chicago skyline in the background and Lake Michigan

Let’s be honest: it’s only spring and you’re already dreaming of a summer vacation. If you’ve had the kind of weather that feels grey, rainy, and very much indoors, you probably want to hit the open road and go somewhere with a lot of sun and space. We’re here to help you take a Midwest road trip this summer!

Factoring your car into the equation of safe westward travel is important – especially when all the Midwest’s natural wonders (like rugged mountains and nature trails) and urban gems are sure to distract you in a good way with all their scenic byways. It is such a great place that you’ll want to spend the most time possible enjoying the small towns that make up America’s Heartland and zero time worrying about your vehicle. A successful experience depends on you having a solid travel plan as well as making sure you have affordable car insurance beforehand. 

To get started on your favorite journey of summer 2023 (one of the best road trips there is), let’s look at your upcoming itinerary as well as some car safety advice to keep you “vrooming” from Chicago to Rapid City.

Midwest Road Trip: Important Considerations Before You Go

Before you embark on your Midwest road trip solo or with family, you’ll want to prepare your suitcase, snacks, and car. While there are large cities to explore, the flat plains and expansive farmland mean that being unprepared could lead to miles and miles without resources. Here’s our helpful advice:

  • Pack for hot weather: It can get very humid in the summer and averages between 75 to 85 degrees Fahrenheit. What this means, especially commuting in a car for many hours, is that you need breathable clothing such as loose-fitting shorts, flowy skirts, and shirts that have a few options to moderate their coverage with buttons or zippers. If you have kids, especially consider their wardrobe as they’ll add body heat to the car ride! Be sure and follow safe tips for taking care of your vehicle in excessive heat, as well.
  • Snacks that won’t go bad: Driving through mostly small towns usually means a lack of fresh, healthy food. Even less fresh is food kept in your car that easily rots in the heat! To ensure you’re consuming food that is healthy and safe, go for heat-friendly options such as tortilla chips, salsa (it will last several days sealed and about a day unsealed), pre-made smoothie packets made from dehydrated fruit, nuts and nut butters, and protein bars. All of your items should be stored in a cooler as well.
  • Car maintenance items: One of the things that takes the most heat on a road trip is your tires. For that reason, have a spare handy, frequently check air pressure, and brush up on your tire care know how. 

You will be so happy that you took these simple steps to ready your adventure. And speaking of ready, now it’s time to see all the amazing places you’ll go to before heading back to your home state.

Best Stops and Itinerary for a Midwest Road Trip

Day 1-2: Chicago, Illinois

Even though you’re going to enjoy a lot of farmlands on this trip, you’ll start the journey in a big city… Chi-town or the windy city, that is! Chicago is a must-do known for hot dogs, pizza, jazz, and architecture. While there, you can even combine the best of both worlds by eating a hotdog at a lakefront kiosk in Traverse City specifically chosen for its artistic “wow!” Bring a sweater for the evening because the wind off the Great Lakes can be chilly.  

Day 3-4: Madison, Wisconsin

On your way out of Chicago, you’ll drive on the Great River Road for just enough time to see its beauty along the Mississippi River. Then, just two-and-a-half-hours (don’t you just love scenic drives?!) northwest is Madison – which basically means the beer, cheese, and waterfront views portion of your Midwest road trip! Given the possibility that you may throw back a cold one or two, remember to choose a designated sober driver in advance and to take time reading up on safe driving tips. In Madison, you may also enjoy the Olbrich Botanical Gardens, Henry Villas Zoo, and the Wisconsin State Capitol.  

Young couple stands in front of the Minneapolis skyline at night

Day 5-6: Minneapolis, Minnesota

The commute to Minneapolis is a bit longer than your previous drive time – especially if you detour into Grand Rapids, so here’s a pro tip: do the drive on a Tuesday when incidents of car crashes are the lowest they’ll be all week (according to the NHTSA (National Highway Traffic Safety Administration). After two days of cities, you probably want to check out nature! Exploring Minneapolis is one of the best ways to have an outdoor experience with places like Minnehaha Regional Park and Fort Snelling State Park.  

Day 7-8: Kansas City, Missouri

The price you’ll pay for a nearly seven-hour drive with tolls isn’t so bad when you hear this news: You get to stay in Missouri for two whole days! Missouri has wonderful museums like the National WWI Museum and Memorial, The Nelson-Atkins Museum of Art, and the Arabia Steamboat Museum. When not indulging your artistic side, Kansas City is well known for Kansas-style barbecue and theater.   

Day 9-10: St. Louis, Missouri

Just three hours further west into your Midwest road trip is St. Louis. Some of St. Louis’ claims to fame are the Gateway Arch Monument and ice-cream cones! We agree, your summer vacation is basically turning into a life of food and fun. Before it ends though, you still have time to see South Dakota, which is where you’ll go next…  

Day 11-12: Rapid City, South Dakota

Rounding out your road trip this summer is stunning Rapid City. Also known as the City of Presidents, Rapid City is a popular spot where you will finally get to see the faces of leadership etched in stone you’ve always been curious about known as Mount Rushmore (say “hi” to Ulysses S. Grant and Abraham Lincoln for us). At this point you will be having such a good time that returning home won’t feel right… so it’s best to head to Badlands National Park for some quiet time in what can only be called “alien-looking terrain.”

Then, you have the choice to fly out of South Dakota (sorry North Dakota, you’ll get a visit on the next trip) or to drive back to Chicago (being sure not to skip a hike in Shawnee National Forest on the way).  

Tips for Affordable Midwest Road Trip Adventures

We want to let you in on some of the best ways for completing your Midwest road trip the affordable way this summer. To save some money while road tripping, choosing a cheaper hotel or the “rent a room” option instead of “renting a full Airbnb” for accommodations is a great way to save money on your perfect place.

You can also plan to make your meals, so you don’t have to eat out all the time by having some groceries on hand. Last, but not least, you can save on major unexpected expenses by making sure your car (or rental!) is “vacation insured” and operating well.  

Road Trip Essential: Car Insurance for Your Midwest Adventure

Now that you are ready to traverse the summer on one of the best Midwest road trips at a beautiful time of year, all you have to do is secure affordable car insurance today from Freeway Insurance and you’re basically a Midwesterner already. Get a fast and free quote online, give us a call at 800-777-5620 or stop by one of our convenient locations. Have the best time all across the smaller towns and rolling terrain of the United States!

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