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.
The floodplain of the Upper Mississippi River from a bluff.
Sandstone cliffs along the Wisconsin River at the Dells.
The historic railroad depot in Wisconsin Dells.
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
The World's Largest Buffalo above Jamestown, home of the National Buffalo Museum.
Downtown Fargo, just across the Red River from Minnesota.
Sweetbriar Lake on I-94 west of Mandan.
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
The trail at Painted Canyon Overlook.
Geese in Flight at the I-94 exit for the Enchanted Highway.
Bands of red scoria, tan clay, and gray bentonite stripe the buttes at Painted Canyon, where the erosion of ancient river sediments carved the North Dakota Badlands over millions of years. (Wikimedia Commons)
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.
The Elkhorn Ranch site today, where none of the ranch buildings still stand.
The view east from the Oxbow Overlook in the North Unit.
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
Mount Rushmore National Memorial in the Black Hills.
Bison in Custer State Park, home to one of the largest public herds in the country.
Boxwork in Wind Cave. Most of the world's known boxwork is found here.
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.