In Part 5 of our cross-country road trip, we trade the skyscrapers of Chicago for wide-open skies and winding prairies. As we journey westward, the bustling cityscape fades in the rearview mirror, replaced by rolling farmland, quiet rivers, and small-town Americana. Our destination: the rugged beauty of Badlands National Park in South Dakota – a stretch of road that delivers the ultimate U.S. road trip vibes.

Leg 5 of 11: Overview

This leg of the trip could be done in a long day’s drive, but that would mean missing the charm of the Midwest’s backroads and hidden gems. As always, the journey is just as important as the destination.

Leaving Chicago: Into the Wide Open

After soaking in the buzz of the Windy City – think skyline views, deep-dish pizza, and lakefront strolls – we hit the road on Interstate 90, heading west. Urban sprawl quickly gives way to flat horizons and an ever-changing sky. The Midwest unfolds ahead like a classic American novel.

Stop 1: Madison, Wisconsin

Nestled between two scenic lakes, Wisconsin’s capital offers a refreshing mix of nature, culture, and that laid-back university town energy.
Willy Street: Quirky cafés, indie shops, and local flavor.
Capitol Square: The imposing State Capitol is well worth a quick tour.
Farmers Market (Saturdays): One of the largest in the country, held right on the Capitol’s doorstep.

Detour: Wisconsin Dells

Yes, it’s kitschy. And yes, it’s absolutely worth it. Known for its sandstone formations and family-friendly waterparks, Wisconsin Dells is equal parts natural wonder and nostalgic fun. Take a river boat tour or embrace the Americana — either way, it’s a blast from the past.

Stop 2: La Crosse, Wisconsin

Situated along the Mississippi River, La Crosse is green, peaceful, and full of historic charm.
Grandad Bluff: A scenic overlook with sweeping views of the river valley.
Riverside Park: A perfect stop for a coffee or picnic by the water.

Stop 3: Sioux Falls, South Dakota

The largest city in South Dakota makes for an ideal overnight stay – clean, modern, and packed with creativity and nature.
Falls Park: Natural waterfalls right in the heart of downtown.
Sculpture Walk: A walkable open-air art exhibit throughout the city center.

Cultural Detour: Akta Lakota Museum & Cultural Center

Just off I-90 in Chamberlain, the Akta Lakota Museum offers a powerful look into the culture and heritage of the Lakota people. Situated on the banks of the Missouri River, this small but moving museum is a quiet, meaningful stop.

Stop 4: Badlands National Park

After hours of driving through rolling hills and wide skies, the jagged ridges of the Badlands rise suddenly from the prairie – surreal, silent, and unforgettable.

Don’t miss:

• Scenic Byway 240: A drive-through showcase of the park’s best views.
• Fossil Exhibit Trail: A short, family-friendly walk with fascinating insights into the park’s prehistoric past.
• Sunset Views: As the sun dips low, the rocks glow in brilliant reds and oranges – a must-see moment.

Reading tip: A Day in the Badlands – Between Rugged Rock Formations and Prairie Dogs

Travel Tips for This Stretch

• Fuel Up: Gas stations and general stores become sparse in South Dakota – don’t push your luck!
• Off the Beaten Path: For more natural beauty, take state highways and country roads after Madison — you’ll pass through serene small towns and lovely state parks.

Our conclusion: From the urban pulse of Chicago to the silent spires of the Badlands, this leg of the journey captures a dramatic shift – from city lights to prairie skies. It’s a stretch of road that reminds you just how vast and varied the American landscape can be. Up next: We continue our adventure in South Dakota – stay tuned.

Indigenous history, a riverside picnic, or endless prairie views – what’s your highlight?
Let us know in the comments & tag your favorite road trip buddies!

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