Chicago to the Badlands: The Long Way

About 965 miles · 14 hours of driving · 7 to 9 days

Chicago to Medora is I-90 and I-94 almost the whole way — through Wisconsin, across the Mississippi, over Minnesota and the width of North Dakota. It is two days of driving each way, and the country changes completely while you do it: hardwood and lake, then prairie, then Badlands.

The Badlands are the destination. What follows is how to get there without wasting the getting there.

Drive times assume summer conditions. This route crosses into Mountain Time at the North Dakota border west of Bismarck.

View from a bluff over the wooded floodplain and open water of the Upper Mississippi River under a cloudy sky

Day 1: Chicago to the Mississippi

Out of the city on I-90 and across Wisconsin. This is the prettiest stretch of the eastern half — the Driftless Area, the corner of the upper Midwest the last glaciers missed, so instead of flattened plain you get carved river bluffs and coulees.

  • Madison at about 2.5 hours — the isthmus between two lakes, and a good lunch stop.
  • Wisconsin Dells — sandstone gorges on the Wisconsin River under all the waterpark signage. The boat tours through the Upper Dells are the reason to stop.
  • The Mississippi crossing at La Crosse or Prairie du Chien — the Upper Mississippi River National Wildlife and Fish Refuge runs 260 miles along here, and the bluff overlooks are worth pulling off for.

~5 hours to the river · overnight La Crosse or the Twin Cities

A herd of bison grazing beside the Wildlife Loop Road in Custer State Park, with a car stopped among them

Day 2: across Minnesota and into North Dakota

Through the Twin Cities and onto I-94 for the long westward run. The trees thin out somewhere past St. Cloud and do not really come back.

  • Minneapolis–St. Paul — worth a night on the way out or back if you have the time.
  • Fargo at the state line, about 3.5 hours past the Twin Cities.
  • Jamestown, ND — the National Buffalo Museum and the World’s Largest Buffalo, a 26-foot concrete bison with a live herd grazing below it.
  • Bismarck — the North Dakota Heritage Center & State Museum, free and directly on the interstate, and the best single hour between Chicago and Medora.

~9 hours · overnight Bismarck, or push the last 2 hours to Medora

Two visitors on the trail at Painted Canyon Overlook, with layered badlands buttes stretching to the horizon under a bright sky

The last hour: the Enchanted Highway and Painted Canyon

The final stretch of I-94 has the two best roadside stops on the whole route, and they arrive within 40 miles of each other.

  • The Enchanted Highway at Exit 72 near Gladstone. Geese in Flight stands 110 feet tall beside the interstate and holds the Guinness record for the largest scrap-metal sculpture in the world. The full run is 32 miles south to Regent, past Teddy Rides Again and the World’s Largest Tin Family. Add 2 hours for the whole thing, or look at the geese and drive on.
  • Painted Canyon Overlook at Exit 32 — the first proper view of the Badlands, and the one that makes the drive feel worth it.

Then 15 minutes to Medora

The Theodore Roosevelt Presidential Library on the butte above Medora, with the badlands below and storm clouds overhead

Days 3–5: Medora and the Badlands

This is what you drove for.

Roosevelt came to this country in 1883 and it rebuilt him. The Theodore Roosevelt Presidential Library, above the town on the bluff, is the anchor of the stop — give it most of a day, not an hour. The galleries run from a sickly New York boy to the president who put 230 million acres under protection, and the building sits in the landscape it is about.

  • Day 3 — the Library. Galleries (2–3 hours), the Boardwalk over the bluff, lunch at the Library Café. Afternoon on the South Unit scenic loop: 36 miles, about 1.5 hours with stops, for bison, prairie dog towns and wild horses.
  • Day 4 — go further out. The Elkhorn Ranch site, where he built his home ranch and where nothing is left standing (half a day, gravel roads, check conditions), or the quieter North Unit ninety minutes north.
  • Day 5 — Medora itself. The Chateau de Mores, the Cowboy Hall of Fame, the Maltese Cross Cabin. In summer, the Medora Musical and the Pitchfork Steak Fondue — book both ahead.

Three nights in Medora

Aerial view of the Mount Rushmore carving in the granite of the Black Hills, surrounded by ponderosa pine

Days 6–7: the way home

Retracing I-94 is the fast way — two days and you are back. But there is a better version if you have the time.

  • Swing south through the Black Hills. From Medora it is about 5 hours to Mount Rushmore, Custer State Park and Wind Cave National Park, which Roosevelt made the eighth national park in 1903.
  • Devils Tower, the first national monument in the country, is 3 hours from Medora and roughly on the way to the Hills.
  • From Rapid City, pick up I-90 east and run it home through South Dakota and Minnesota — about 14 hours to Chicago, so two days.

That loop turns a 7-day trip into 9 or 10 and adds three national parks for almost no backtracking.