Midwestern Itineraries

Search All Our Itineraries or Browse Midwestern Itineraries Below

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

North Shore Chicago Itinerary

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...

Things To Do in Springfield, MO

Things To Do in Springfield, MO

Three Day Itinerary for Groups in Springfield, MO Springfield, Missouri, is a vibrant city that blends rich history, outdoor adventure, and modern attractions, making it a perfect destination for group travelers. Nestled in the heart of the Ozarks, Springfield offers...

Elgin, Illinois Itinerary

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

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

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...

Lake County, IL Itinerary for Travel Groups

Lake County, IL Itinerary for Travel Groups

Lake County, Illinois is Home to Hidden Treasures and Country Pleasures Enjoy a three-day tour to amazing hidden gems just north of Chicago From the flower-filled meadows of the Lake County Forest Preserves to outdoor festivals, live events and a range of shopping...