Chicago to Dakota Black Hills to Yellowstone Road Trip

See the Badlands, Mount Rushmore, Deadwood, Devils Tower, and more on this 12-day loop through South Dakota to Yellowstone and back through North Dakota.
By Staff,
Devil's Tower near Gillette in eastern Wyoming

Road Trip Overview

It's an all-American road trip: Pioneer legends, natural wonders and wildlife await on this 2,800-plus mile route.

Start in Chicago as your first stop on this incredible route through some of the nation's most stunning prairies, wide-open skies and gorgeous mountain peaks.

From Chicago head west, stopping at the Akta Lakota Museum to discover northern Plains Indian history. Then head to the iconic Wall Drug in South Dakota and Badlands National Park. Beyond lies Mount Rushmore in Keystone, S.D., hot springs in well, Hot Springs, S.D., and two national parks that give you a rare glimpse into the underbelly of the Earth: Wind Cave and Jewel.

Come up for air and head to Custer for Broadway-caliber performances and wildlife viewing at nearby Custer State Park. Then head to the Crazy Horse Memorial, the largest monument carving in the world. This sculpture of Oglala Lakota Chief Crazy Horse is still under construction. Head to Deadwood to walk cobblestone-lined Main Street and to see Wild West reenactments. In Hill City, you'll ride The 1880 Train and in Belle Fourche, you can tour a museum and relax under shaded trees. In Wyoming, Gillette makes a great base to explore Devils Tower National Monument and Thermopolis offers dinosaur digs. After exploring Yellowstone National Park, head to Billings, Mont., and Medora, N.D., en route to Chicago.

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Road Trip Itinerary

Start: Chicago

Cloud Gate, a kidney-bean-shaped sculpture in Chicago

In Chicago, join locals and travelers alike at Millennium Park downtown. A showcase of who's who in architecture, this interactive park is an adult playground. Check out these three architectural gems.

See Cloud Gate, a kidney-bean-shaped sculpture that’s 66 feet long and 33 feet high. Made with polished stainless steel, the sculpture features an arch that enables you to walk under it and see your contorted reflection in the steel walls. It’s the first public outdoor work of British artist Anish Kapoor in the U.S.

Catch a music show at the Jay Pritzker Pavilion. Designed by architect Frank Gehry, this outdoor concert venue has 4,000 fixed seats and room for an additional 7,000 people on the Great Lawn.

Discover the Crown Fountain, which features the faces of 1,000 Chicago residents on two 250-foot glass towers, each one at the opposite end of a shallow reflecting pool. It's designed by Spanish artist Jaume Plensa, known for creating monumental public art.

Stop 1: Central, South Dakota

Akta Lakota Museum & Cultural Center

Exhibit at the Akta Lakota Museum and Cultural Center in Chamberlain, S.D. Courtesy photo

Move clockwise through the museum from "Pre-European" to "Two Worlds Meet" to "Broken Promises" and finally "Continuity and Change."
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Wall, South Dakota

The famous Wall Drug Store in Wall, S.D.

If it wasn’t for ice water, the famous Wall Drug in Wall, S.D. may have just been another casualty of the Great Depression that swept the nation and shuttered one business after another.

When it opened in 1931, owners Ted and Dorothy Hustead waited for a steady stream of customers that never arrived. After five years, Dorothy Hustead decided it was time to hang signs on the highway advertising free ice water. The free ice water has brought a torrent of customers in ever since, totaling up to 20,000 people on good days.

Stop by Wall Drug at 510 Main St., in Wall, S.D., for its burgers, 5-cent coffee, a photo of its famed Jackalope statue and of course, some free ice water.

Badlands National Park

Badlands in South Dakota

Spend a day with a trip to Badlands National Park. The multicolored, crinkled geologic formations of the Badlands draw hikers, wildlife-watchers and geology buffs. Nearby, visit the Minuteman Missile National Historic Site for a look at two 1960s missile sites preserved for education about the Cold War.
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Stop 2: Black Hills, South Dakota

Exit I-90 South before entering Rapid City and head to Hot Springs, S.D.

Hot Springs, South Dakota’s Top 6 Things to Do in Mammoth Country

Evan's Plunge. Photo by Justin Gausman courtesy of Hot Springs, S.D.

Hot Springs is home to the world-famous Mammoth Site, a Wild Horse Sanctuary, Evans Plunge, Wind Cave National Park, and a watery oases.
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Explore Three National Parks and Monuments in the Black Hills

Boxwork on a cave's ceiling at Wind Cave National Park in South Dakota

Journey deep into the Earth on a tour of one of the world’s most complex cave systems at Wind Cave National Park. See the faces of four U.S. presidents: George Washington, Thomas Jefferson, Theodore Roosevelt and Abraham Lincoln, carved in stone at Mount Rushmore National Memorial. And at nearly 153 miles long, Jewel Cave National Monument is the second longest cave in the world.
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Custer is South Dakota’s Yellowstone

Bison herd in Custer State Park in South Dakota

Watch more than 1,300 bison roam free at Custer State Park, then head for Custer's historic downtown, a hive of restaurants, shopping and museums.
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Crazy Horse Memorial

A Native American dancer with a view of Crazy Horse Memorial in the background. Courtesy photo

Near Mt. Rushmore in South Dakota, another rock carving in process honors Crazy Horse, the legendary Lakota leader, and his people.
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Rushmore Tramway Adventures

Aerial Adventure Park. Photo courtesy of Rushmore Tramway Adventures

Just two miles below Mt. Rushmore, is this outstanding collection of outdoor adventures: President’s Alpine Slide, Rushmore Tramway’s chairlift, Mountaintop Grille and Gardens, Aerial Adventure Park’s ropes courses, and the breathtaking new Pinnacle Zipline Tour.
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Hill City is the Heart of the Hills. Ride the 1880 Train.

The 1880 Train in Hill City, SD. Courtesy Photo

Climb aboard The 1880 Train, a 2-hour, 20-mile ride aboard an authentic steam train. The historic train runs between Hill City and Keystone, S.D. Then discover the beauty of the 109-mile George S. Mickelson Trail or watch a summer performance of Brule, a New Age blend of contemporary Native American music.
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Deadwood, South Dakota Has Been Entertaining Since 1876

Gunfight re-enactment in Deadwood, S.D. Courtesy photo

History. It’s what you’ll find when you walk in the footsteps of Wild West legends, visit graveyards, and watch re-enactments. Try your luck in gaming halls.
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Lodging in the Black Hills

Lodge at Deadwood
Stay at The Lodge at Deadwood Gaming Resort to experience the past in the luxury of today. (877-393-5634,

Black Hills Vacations
Black Hills Vacations Central Reservations can book lodging, attractions, and packages. (888-636-0626,

Executive Lodging of the Black Hills
Choose from 50 luxury lodges in the Black Hills. (866-370-3555,

Stop 3: Get Centered in Belle Fourche

Johnny Spaulding Cabin. Photo courtesy of the Tri State Museum and Visitor Center in Belle Fourche, S.D.

On your way west, out of the Black Hills, see silver spoons that traveled on the Mayflower in 1620 and antique saddles at the Tri-State Museum. Then take a selfie at the Geo-Center monument.
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Lodging in Belle Fourche

Super 8 (605-892-3361,

AmericInn (605-892-3444,

Stop 4: Eastern Wyoming

Devils Tower National Monument

Devil's Tower. Photo by B D via Wikimedia Commons

Travelers roaming through the northeastern Wyoming prairie will be treated to a strange and wonderful sight: a striking stone column rising seemingly out of nowhere.
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Gillette & Wright, Wyo.

Bison herd at the Durham Bison Ranch near Wright, Wyo. Photo courtesy of Campbell County

The top six things to do when you stop on your way from theBlack Hills to Yellowstone include tours, train spotting, a museum, and a brewery.
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Paradise Guest Ranch in Buffalo, Wyo.

Paradise Guest Ranch in Wyoming. Courtesy photo

For 100 years, folks have been doing week-long vacations at the Paradise Guest Ranch. Go horseback riding, fishing, hiking, and spend time with the family.
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Stop 5: Thermopolis, Wyo.

Things to Do in Thermopolis

Hot Springs State Park in Thermopolis, Wyoming

Stop at favorite restaurants, the hot springs park, and a museum at this small, picturesque town where the elevation is higher than the population.
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Wyoming Dinosaur Center

Dinosaur skeletons at the Wyoming Dinosaur Center in Thermopolis. Courtesy photo

Unearth your inner paleontologist. At of the best dinosaur museums in the world, locate the prehistoric dinosaurs beneath Thermopolis on a Dig for a Day adventure.
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Stop 6: Yellowstone National Park

Lodging between Cody, Wyoming and Yellowstone's East Entrance

Elephant Head Lodge
Just short of the park's entrance, stay or eat at Elephant Head Lodge built by Buffalo Bill's family. (307-587-3980,

Dude Rancher's Association
Experience a real Wyoming cowboy experience by staying at a dude ranch near Cody. (866-399-2339,

Lodges of East Yellowstone
Call Lodges of East Yellowstone to stay in a log cabin right outside the park's entrance, some with home-cooked meals. (307-587-9595,

Buffalo Bill Village Resort
Stay in one of three distinctive hotels at the Buffalo Bill Village Resort in Cody. The Holiday Inn, the Comfort Inn and the Buffalo Bill [Cabin] Village, each are convenient base camp for families, groups and corporate retreats. (307-587-3654,

Yellowstone Activities

Boat tour on Lake Yellowstone

Close to the east entrance of the park is Yellowstone Lake, the waterfalls of the Grand Canyon of the Yellowstone, and the West Thumb Geyser Basin. Spend a day exploring the scenery, hiking, camping and watching wildlife at Yellowstone National Park. See our favorite park itineraries.

GyPSy Guide Yellowstone Tour App

Yellowstone GyPSy Guide App for your cell phone or tablet

Download the Yellowstone tour app that’s like having a tour guide in your car. GyPSy Guide automatically plays interesting and entertaining commentary as you go.
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Stop 7: Montana Gems

Cooke City, Montana

Downtown Cooke City. Photo by Patty Pickett

During the summer, exit Yellowstone National Park near this tiny burb to travel over the dramatic Beartooth Highway towards Billings. (In winter, the highway is closed. Exit the park out of Gardiner, Montana instead.)

Billings, Montana

View from Sacrifice Cliff overlooking the Yellowstone River. Photo courtesy of Billings, Montana

Here are the top 7 places to find vittles and lore in Billings, including a walkable brewery district, a restored historic hotel, wilderness touched by Lewis & Clark, and a memorial to a famous battle.
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Lewistown - The Heart of Montana

Montana elk grazing in early summer

From big game hunting to fishing, camping, biking, hiking and skiing, take advantage of the outdoor recreation opportunities in the beautiful Judith Basin. Board the Dinner Train, the Charlie Russell Chew Choo, to ride a scenic 56-mile roundtrip journey with great views of wildlife, full-course prime rib dinner, and music by local area entertainers.
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Traveling in August? Don't miss the Cowboy Poetry Gathering and Western Music Rendezvous.

Lodging on the Way to North Dakota

Stay at the Sleep Inn in Miles City, Mont., a good stopping point between Billings and Medora. Receive a $25 gift card from Town Pump when you request the "Stay & Save" package when making reservations. (800-442-4667,

Stop 8: North Dakota

Theodore Roosevelt National Park

Badlands Formations in Theodore Roosevelt National Park

This 3-unit park is known for amazing wildlife (bison and elk), 95 miles of hiking trails, horseback riding, water sports, and inspiring a president.
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Medora, North Dakota's Top 6 Experiences

Chateau de Mores State Historic Site in Medora, N.D.

Discover a cabin, national park, and theater devoted to one of the greatest conservationist presidents, Theodore Roosevelt. Plus a 150-mile trail and chateau.
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End: Chicago

Take the northern route home through North Dakota, Minnesota and Wisconsin. Minneapolis marks the halfway point.