Residing minutes from Madison, Middleton offers the perfect blend of outdoor adventure, local flavor and small-town charm for a three-day escape.
Midwestern Itineraries
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Midwestern United States
The Midwest is a lovely region in the country that sports both flat terrain and rolling hills from state to state. It is also home to a fabulous array of alluring cities and towns that will keep your group entertained. Home to exciting big cities like Chicago and beautiful states brimming with natural wonders like Michigan, the Midwest will have your group clamoring for more. And don’t forget, the country’s biggest mall, the Mall of America in Minnesota, features more than 5.6 million square feet of shopping fun.
Browse Midwestern Itineraries
Where the Mother Road Meets the River Road
There’s only one place in America where the Mother Road of Route 66 meets the Great River Road and that’s in southwest Illinois.
Champaign-Urbana Itinerary: Illinois Parks and Dining Experiences
Embark on a trip through east-central Illinois and experience the rich culture and outdoor excursions.
A Taste of Fall in Southern Indiana
Step into Southern Indiana’s fall charm, where historic river towns meet sweet traditions, steamboat history and rolling wine country.
Three Days on the Great River Road in Southwest Illinois
The Great River Road is a scenic treasure in the Land of Lincoln, offering breathtaking views of the Mississippi River, charming small towns, and historic landmarks.
North Shore Chicago Itinerary
Three Days of Leisure and Learning on Chicago’s North Shore Chicago’s North Shore offers a perfect blend of natural beauty, architectural wonders, and rich history, making it an ideal destination for a three-day getaway. Nestled along the shores of Lake Michigan, this...
Elgin, Illinois Itinerary
Exploring the Best of Elgin and Beyond Less than an hour’s drive from downtown Chicago, the Elgin Area abounds with exciting options for tour groups. They can stroll the historic districts of Elgin, ride an antique trolley, try their luck at a popular riverboat casino...
2-Day Itinerary on Route 66 in Illinois
Experience Iconic Route 66 Attractions in Illinois With the nationwide celebration of the Route 66 Centennial coming up in 2026, interest in the famous highway has never been higher. Springfield abounds with attractions that recall the glory days of cruising along the...
3-Days to Experience Champaign-Urbana, IL
Champaign-Urbana in 72 Hours–Amish Traditions, Artistic Inspiration, and Agricultural Adventures This three-day itinerary will leave you with a newfound appreciation for the region’s hidden gems, from farm-to-table dining experiences to charming small-town...