Midwest to Rockies Road Trip: A 2-Week Adventure from Chicago
- Tony Albert
- Aug 7, 2025
- 5 min read
Discover the Best Midwest to Rockies Road Trip for Retirees
Are you retired—or close to it—and looking for a road trip of epic proportions? If you’ve got a little time and a lot of curiosity, we’ve cooked up a 2-week adventure just for you. This Midwest to Rockies road trip is perfect for retirees who love to travel, soak in history, and take in jaw-dropping scenery. From charming towns to legendary landmarks, this trip is equal parts relaxing and unforgettable. We even included fun stops, easy hikes, and great places to stay.
Ready for the Midwest to Rockies road trip of a lifetime? This two-week loop from Chicago takes you through the heartland of America and into the stunning beauty of the Rocky Mountains. Along the way, you’ll uncover stories from America’s past, explore charming towns, and experience awe-inspiring natural landmarks. Whether you're a history buff, a scenic traveler, or someone looking to blend the two, this route has something for everyone.
Trip Snapshot: Midwest to Rockies Road Trip Highlights
Start/End: Chicago, IL
Duration: 14 Days
Total Miles: ~3,000
Ideal Time: May–October
Focus: Historical points of interest, natural wonders, charming towns, iconic Americana, scenic landscapes
Day 1: Chicago to Madison, WI
Drive Time: 2.5 hours
Highlights: Madison, the capital of Wisconsin, is a vibrant university town nestled between Lakes Mendota and Monona. It offers a great mix of culture, history, and lakeside views. Start with a visit to the Wisconsin State Capitol, modeled after the U.S. Capitol and open for free tours. From there, take a stroll down State Street, lined with cafes, boutiques, and bookstores, connecting the Capitol to the University of Wisconsin campus. If you’re a fan of architecture, check out Monona Terrace, a lakeside convention center designed by Frank Lloyd Wright.
For nature lovers, the Olbrich Botanical Gardens offers a peaceful escape—don’t miss the gold-tipped Thai Pavilion, a gift from the Thai government. If you time it right, catch the Dane County Farmers’ Market on Capitol Square, one of the best in the country.
Stay: Downtown Madison boutique hotel or lakeside Airbnb
Day 2: Madison to Minneapolis, MN
Drive Time: 4 hours
Highlights: Stop in Baraboo to explore the Circus World Museum, birthplace of the Ringling Brothers. Grab lunch in La Crosse along the Mississippi River and take in the Grandad Bluff overlook. Once in Minneapolis, check out the Stone Arch Bridge and Mill District along the Mississippi for a scenic walk.
Stay: Hotel in the Mill District or riverside Airbnb
Day 3: Minneapolis to Sioux Falls, SD
Drive Time: 4 hours
Highlights: Visit Pipestone National Monument to see ancient Native American quarries and walk the Circle Trail. In Sioux Falls, check out Falls Park and the SculptureWalk through downtown.
Stay: Historic downtown inn or modern hotel
Day 4–5: Sioux Falls to Badlands & Black Hills, SD
Drive Time: 5 hours
Highlights: The Badlands offer an unforgettable landscape of jagged buttes, fossil beds, and prairies. Hike the Notch Trail and visit the Ben Reifel Visitor Center. Wildlife sightings may include bison, prairie dogs, and bighorn sheep. Don’t miss a quirky stop at Wall Drug on the way to the Black Hills. Continue to Mount Rushmore and Crazy Horse Memorial to see iconic monuments and ongoing artistry.
Stay: Keystone or Custer area, or in Custer State Park
Day 6–7: Black Hills to Cody, WY (via Devil’s Tower)
Drive Time: 6 hours
Highlights: Explore Deadwood, a Wild West town full of legends. Catch a shootout reenactment or visit Mount Moriah Cemetery. Head west to Devil’s Tower, the first U.S. National Monument and a sacred site. Continue to Cody and dive into the Buffalo Bill Center of the West, a museum complex packed with Old West history and Native American exhibits.
Stay: Cody Cowboy Village or Irma Hotel
Day 8–9: Yellowstone National Park
Drive Time: 1.5 hours from Cody
Highlights: Visit Old Faithful, Grand Prismatic Spring, and Mammoth Hot Springs. Take your time exploring Yellowstone Lake and Lamar Valley, especially for wildlife viewing. The park’s geothermal features and expansive scenery are unlike anywhere else.
Stay: In-park lodging or nearby cabin
Day 10: Yellowstone to Estes Park, CO
Drive Time: 6–7 hours
Highlights: Pass through Casper or Laramie for a break, and consider a stop at the National Historic Trails Interpretive Center in Casper. Arrive in Estes Park and settle into your mountain retreat.
Stay: Estes Park lodge or The Stanley Hotel
Day 11: Rocky Mountain National Park
Highlights: Take Trail Ridge Road for sweeping alpine views and wildlife sightings. Stop at the Alpine Visitor Center and walk the Bear Lake Loop Trail. Visit the Holzwarth Historic Site to glimpse life as it was in the early 1900s. Spend the evening strolling the charming downtown area of Estes Park, and consider a ghost tour at The Stanley Hotel.
Stay: Same as Day 10
Day 12: Estes Park to Hays, KS
Drive Time: 6 hours
Highlights: Detour to the Kit Carson County Carousel in Burlington, CO for a nostalgic stop. Once in Hays, check out the Fort Hays Historic Site and local art in downtown.
Stay: Locally-owned hotel or roadside inn
Day 13: Hays to Kansas City, MO
Drive Time: 5 hours
Highlights: Stop in Abilene to explore the Dwight D. Eisenhower Presidential Library and Museum. Continue to Kansas City and enjoy BBQ, jazz history, and Union Station.
Stay: Crossroads Hotel or The Fontaine
Day 14: Kansas City to Chicago, IL
Drive Time: 7 hours
Highlights: In Hannibal, Missouri, tour the boyhood home of Mark Twain and explore the Mark Twain Cave. Continue to Springfield, Illinois, and explore Abraham Lincoln’s home and the Lincoln Presidential Library and Museum.
Wrap-Up: Finish back in Chicago with a Lake Michigan walk or deep-dish pizza at a local favorite.
Final Tips for the Road
Download offline maps before heading into remote areas
Book park lodges 6+ months in advance
Pack layers for elevation changes
Keep binoculars handy for wildlife
This Midwest to Rockies road trip offers a perfect blend of history, nature, and good old-fashioned road travel. Whether it’s your first big trip after retirement or your tenth cross-country loop, this route is designed to help you experience the best of what America has to offer—one scenic mile at a time.
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