Unforgettable Road Trip Through the Midwest
People who’ve never really considered a visit to “Flyover Country” usually find themselves pleasantly surprised — and sometimes even downright shocked — by just how much there is to see, do, and experience in the great American Midwest, often for free.
Defined by wide-open swathes of farmland, friendly small towns, and attractive urban cities, this down-to-earth territory holds all the makings of a memorable road trip. Enjoy a less expensive journey with lower prices for gas and lodging compared to coastal destinations, making it easy to explore the heartland’s culture and attractions.
St. Louis – Missouri
With affordable attractions, tasty food, and a unique river city culture, St. Louis makes a great starting point for a Midwestern road trip. At 630ft, the iconic Gateway Arch is a must-see and is America’s tallest man-made monument. The recent CityArchRiver project revamped the landscape around the landmark, enriching it with green spaces and bike trails.
For the best views, take the tram ride to the top or enjoy a cruise on the mighty Mississippi aboard a paddlewheel-powered riverboat. During baseball season, the energy at Busch Stadium is palpable with avid Cardinals fans cheering for their team. Even if you’re not attending a game, the vibrant atmosphere is infectious.
Explore the historic Forest Park, which features free museums, a zoo, a science center, a greenhouse, lakes, and extensive walking paths. Don’t miss the chance to tour the Anheuser-Busch Brewery grounds and indulge in classic fried ravioli at local Italian restaurants.
Route 66 Heritage Project – Illinois
Gearing up to celebrate its centennial in 2026, America’s Mother Road stretches for 300 miles through Central Illinois from St. Louis to Chicago. Cross the Mississippi River at the Chain of Rocks Bridge and enjoy the scenic views as you head northeast to experience the charm of small towns like Litchfield, Springfield, and Pontiac.
Commemorate your journey with snapshots against Americana-rich backdrops, including the 30ft Gemini Giant and Paul Bunyon holding a hot dog. For a traditional experience, consider staying in a local motel and refueling at Dell Rhea’s Chicken Basket.
Chicago – Illinois
Chicago, the Windy City, offers a winning combination of history, sports, food, and culture, inviting visitors to explore its vibrant neighborhoods and iconic landmarks. Start at the Museum Campus, home to attractions like the Shedd Aquarium and the Field Museum.
After strolling through Millennium Park and taking some iconic photos at the Bean, enjoy the Ferris wheel at Navy Pier and shop along the Magnificent Mile. Chicago is alive with a strong theater community, offering entertainment options nearly every night of the week.
Be sure to indulge in local favorites such as deep-dish pizza or a Chicago-style hot dog, completing your culinary experience in this vibrant city.
Milwaukee – Wisconsin
Travel an easy 90-minute drive north from Chicago to reach Milwaukee, a city rich in culture and history. Visit the Harley-Davidson Museum, which is a pilgrimage site for many brand enthusiasts. Learn about the city’s beer heritage with a tour of local breweries such as Miller or Sprecher.
Sample Wisconsin staples, including cheese curds and butter burgers, at Milwaukee’s vibrant Public Market. With beautiful riverfronts and a thriving arts scene, Milwaukee presents numerous opportunities for outdoor recreation and cultural enrichment.
Green Bay – Wisconsin
This historic city is home to the Green Bay Packers, allowing fans to visit Lambeau Field and experience the passionate sports culture. Aside from sports, the area is surrounded by breathtaking scenery and offers numerous hiking opportunities amidst stunning landscapes.
Duluth – Minnesota
As you continue your journey, head to Duluth. Situated on the shores of Lake Superior, this charming city offers outdoor adventures year-round, especially in fall when the leaves change colors dramatically. The Aerial Lift Bridge stands as a symbol of Duluth, operating frequently to accommodate maritime traffic.
Gooseberry Falls State Park – Minnesota
Conclude your adventure at Gooseberry Falls State Park, renowned for its stunning waterfalls and scenic trails. Enjoy a leisurely walk around the Falls View Loop to appreciate the park’s beauty, and make sure to treat yourself to a sweet dessert at a local café as a perfect end to your journey.
