If  your planning on visiting the Windy City anytime soon, why not consider a road trip from Chicago to experience more of the Midwest?   After seeing Chicago and its iconic landmarks, we recommend hitting the road and indulging in some wine tasting. Afterwards, venture out to Badlands National Park for car camping and hiking. But the pièce de résistance of this journey will be discovering Mount Rushmore and Custer State Park. We’ve added some packing tips and where to uncover hidden gems and popular attractions along with way. This journey will leave you with unforgettable memories and a new appreciation for the heartland of America.

Day 1-2: Exploring Chicago’s Iconic Landmarks

In our humble opinion, the Art Institute of Chicago is the USA’s finest museum. It’s simply a must-see if you haven’t been.  Spend your first day visiting the museum and then head to the Skydeck at Willis Tower.  Take in the panoramic views of the city from one of the highest points in the Western Hemisphere.

On day two, explore the Magnificent Mile and the Navy Pier. Shop at high-end boutiques, dine at Michelin-starred restaurants, enjoy free public art installations, and take a ride on the Ferris wheel. End the day with a sunset cruise on Lake Michigan, soaking in the beautiful city skyline.

But don’t worry if you can’t see everything in just two days – there’s always a reason to come back to Chicago and explore more of its rich culture and history. Although you should probably make time for some of the best pizza in the world. 

Day 3-4: Wine Tasting in the Heart of Midwest

As we leave Chicago behind, we head towards the picturesque vineyards of the Midwest. Our next stop is in the heart of wine country where we can indulge in the region’s finest wines. With more than 150 wineries located in the area, there’s a variety of options to choose from, whether you prefer reds, whites, or rosé.

Make sure to stop by the historic town of Galena, where you can find a unique blend of old-world charm and contemporary flair. Take a stroll down Main Street and admire the beautifully preserved 19th-century architecture before heading to the local wineries. Visit the Galena Cellars Vineyard and Winery, where you can take a tour of the vineyards, barrel room, and enjoy a tasting of their award-winning wines.

After a day full of sipping and savoring, it’s time to continue our journey in the direction of Mount Rushmore. But before we do, we have one last stop in the heart of the Midwest.

Day 5-6: Car Camping and Hiking in Badlands National Park

After days of driving, sipping wine, and exploring small towns, it’s time to experience the rugged beauty of Badlands National Park. Filled with breathtaking landscapes, the park is teeming with hiking trails, wildlife, and natural wonders that are sure to leave you in awe. Car camp under the stars and wake up to the stunning views of the park’s famous layered rock formations, which are said to be some of the most unique in the world.

During your stay in Badlands National Park, be sure to take a hike to some of the park’s most iconic destinations, such as the Fossil Exhibit Trail, the Notch Trail, or the Pinnacles Overlook. Along the way, keep your eyes peeled for wildlife such as bison, bighorn sheep, and prairie dogs. As you immerse yourself in the natural beauty of Badlands National Park, you’ll quickly realize why it’s a must-visit destination for any Midwest road trip.

Day 7-8: Discovering Mount Rushmore and Custer State Park

As you bid adieu to Badlands National Park, get ready to add more incredible memories to your road trip with a visit to Mount Rushmore and Custer State Park. The iconic Mount Rushmore is a must-visit landmark, featuring the heads of four of America’s most influential presidents carved into the granite face of the mountain. Take a guided tour to learn more about the history and significance of this American landmark.

After experiencing the wonder of Mount Rushmore, head to Custer State Park for a day of exploring. You can take a scenic drive along the Wildlife Loop Road to witness the area’s diverse wildlife, including bison, pronghorn antelope, and bighorn sheep. Don’t forget to bring your camera as you’ll want to capture every moment of this natural beauty.

If you’re feeling adventurous, you can also try hiking one of the park’s many trails or even go horseback riding. And with numerous campsites within the park, you can spend a night or two under the stars, surrounded by the serene setting of nature. After discovering Mount Rushmore and Custer State Park, it’s time to start thinking about packing for the rest of your road trip. From snacks to clothing to road trip essentials, be sure to pack wisely to ensure a comfortable and seamless journey.

Packing for a Road Trip: Tips and Essentials

When travelling by car, especially in a group or with family,  it’s important to pack smartly and efficiently to maintain good moods and harmony all around. Here are some tips and essential items to consider:

1. Snacks: Keep non-perishable snacks on hand to avoid costly and unhealthy fast food stops. Granola bars, trail mix, and fruit are great options.

2. Clothing: Pack clothes for different weather conditions and activities. Layers are key for staying comfortable throughout the trip.

3. Road trip essentials: Don’t forget a first aid kit, sunscreen, bug spray, a map or GPS, and plenty of water.

4. Entertainment: Bring along books, podcasts, and music to keep you entertained during long stretches of driving.

By packing smartly, you’ll be better prepared to make the most of your adventure, whether traveling alone or with your family.  A great way to keep things organized and make it easier to carry things in and out of the car is to invest in some collapsible Trunk Organizers.

Other Options to Consider on Your Midwest Road Trip

From Chicago to Mount Rushmore, a Midwest road trip offers an array of opportunities to explore hidden gems and visit popular attractions. As you plan your journey, consider researching stops along the way that align with your interests. We have focused on some of the biggest attractions, but here are a few other highlights to consider. 

If you’re a fan of architecture, make a stop in Columbus, Indiana, known for its collection of modernist buildings. Explore the Victorian mansions in Galena, Illinois. Nature enthusiasts may want to visit the Indiana Dunes National Park or hike the Ozark National Forest in Arkansas. In St. Louis, see the iconic Gateway Arch or check out the City Museum.

We hope this journey has something for everyone who wants to experience the Midwest. So don’t wait any longer, grab your bags and hit the road today! As John Steinbeck once said, “People don’t take trips—trips take people.” Let this road trip take you on a journey you’ll never forget.

Explore the meori blog, Organize Life for more tips on how to organize and declutter your home, pack for a road trip and keep all your work essentials organized between office and home.