Chicago to Dakota Black Hills to Yellowstone Road Trip
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Road Trip Overview
Start in Chicago 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 South Dakota's capital, Pierre, and onto the iconic Wall Drug and Badlands National Park. Beyond lies Mount Rushmore in Keystone, S.D., hot springs in well, Hot Springs, S.D., and two national park sites that give you a rare glimpse into the Earth's underbelly: Wind Cave and Jewel.
Come up for air and head to Custer for wildlife viewing at 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 history museum and relax under the shade of trees. In Wyoming, Thermopolis offers dinosaur digs, and the 50 miles east of Yellowstone offers an uncrowded experience. After exploring Yellowstone, head to Billings, Mont., and other southeast Montana sights en route to Chicago.
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, Cloud Gate, the kidney-bean-shaped stainless steel sculpture, Jay Pritzker Pavilion designed by architect Frank Gehry, and Crown Fountain which features the faces of 1,000 Chicago residents on two 250-foot glass towers.
Central South Dakota
Exhibit at the Akta Lakota Museum and Cultural Center in Chamberlain, S.D.
Courtesy Akta Lakota Museum
Go Full Circle at the Akta Lakota Museum and Cultural Center
Move clockwise through the museum from pre-European to "Two Worlds Meet" to "Broken Promises" and finally "Continuity and Change."
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Kayaking at Farm Island
Photo courtesy of South Dakota Department of Tourism
3 Stops in Pierre, South Dakota's Capitol
Explore islands, have a hair-raising experience and refuel like a drifter on your all-American road trip through South Dakota.
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Badlands National Park
A grassy trail through Badlands National Park
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48 Hours in the Badlands and Black Hills
Hit the best of the South Dakota parks with these top spots including national parks, steam trains, wild bison and a legendary store.
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Black Hills of South Dakota
Evan's Plunge
Photo by Justin Gausman courtesy of Hot Springs, S.D.
Top 6 in South Dakota's Hot Springs Mammoth Country
Hot Springs is home to the world-famous Mammoth Site, a Wild Horse Sanctuary, far-reaching caves, and a watery oases.
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Boxwork on a cave's ceiling at Wind Cave National Park in South Dakota
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Wind Cave National Park
Journey deep into the Earth on a tour of one of the world’s most complex cave systems. Want more? Visit Jewel Cave National Monument nearby.
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Wild bison in Custer State Park
South Dakota Tourism
Custer is South Dakota's Yellowstone
Basecamp in Custer for incredible access to these 7 legendary Black Hills sites including a park where 1,300 bison roam free.
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Crazy Horse Memorial
Nick Amoscato via Flickr
Crazy Horse Memorial is a Labor of Love
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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Mount Rushmore at sunset
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Mount Rushmore National Memorial
Constructed from 1927-41, the memorial features the faces of four U.S. presidents: George Washington, Thomas Jefferson, Theodore Roosevelt and Abraham Lincoln.
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Pinnacle Zipline Tour.
Photo courtesy of Rushmore Tramway Adventures
Rushmore Tramway Adventures in Keystone
Outstanding collection of outdoor adventures: alpine slide, scenic chairlift, aerial ropes courses, and the breathtaking new Pinnacle Zipline Tour.
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The Soaring Eagle Zipline Ride at Rush Mountain Adventure Park
Rush Mountain Adventure Park
Feel the Rush at Rush Mountain Adventure Park
Spend the day doing adrenaline-filled activities for nearly every age including a coaster, zipline ride, 7-D interactive ride, challenge course and cave.
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The 1880 Train in Hill City
Photo courtesy of Hill City
Ride the 1880 Train through the Heart of the Hills
All aboard! Enjoy a 2-hour, 20-mile ride aboard an authentic steam train between Hill City and Keystone.
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Downtown Deadwood
Courtesy Deadwood Chamber of Commerce & Visitors Bureau
Making History in Deadwood
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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Mount Rushmore National Memorial
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Black Hills Vacations Central Reservations
Talk to Black Hills Vacations for help planning your trip, including Mount Rushmore, Historic Deadwood and South Dakota national park vacations.
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Johnny Spaulding Cabin
Photo courtesy of the Tri State Museum and Visitor Center in Belle Fourche, S.D.
The Tri-State Museum is near the Geographic Center of the Nation
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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Black Hills Rest stops:
The Lodge at Deadwood
The Lodge is one of the newest, most beautiful Deadwood hotels. When you arrive, you won’t be able to take your eyes off the breathtaking panoramic view of the Black Hills and the high plains.
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Executive Lodging of the Black Hills in Sturgis & Deadwood
Rustic homes, log cabins, luxury accommodations, a clubhouse with a swimming pool, and everything in between.
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Super 8 Belle Fourche
Situated on Route 85, our Super 8 Belle Fourche hotel is just minutes from popular attractions like the Center of the Nation Monument and Tri-State Museum.
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Crossing Wyoming
Devil's Tower in eastern Wyoming
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Devils Tower National Monument
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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Thermopolis Hot Springs
Grant Ordelheide
The World’s Largest Mineral Hot Spring is in Thermopolis
It's a small, picturesque town where the elevation is higher than the population. Come soad in the famous mineral hot springs.
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Digging for fossils
Wyoming Dinosaur Center
Dig This at the Wyoming Dinosaur Center
At one 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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View of WWII airplanes turned firefighters, and the Bighorn Mountains near Greybull, Wyom.
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Greybull's Gems
Explore an ancient ocean shoreline and see World War II-era airplanes in this tiny town of 1,800.
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Rest stops:
Elephant Head Lodge
Less than 12 miles from the park, this small resort sits along a national forest. Stay in a log cabin listed on the National Register of Historic Places.
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Lodging of East Yellowstone
Stay among beautiful views with close access to Yellowstone. Enjoy cozy log cabins, home-cooked meals, horseback riding, and RV sites.
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Yellowstone National Park
Enter East Entrance
Grand Prismatic Hot Springs Pool
Grant Ordelheide
48 Hours in Yellowstone
Only have 48 hours? Make the most of your time by visiting some of our favorite spots in the park.
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Audio tour app for your phone
GyPSy Guide's Yellowstone Audio Tour App
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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Bison along Rose Creek in Lamar Valley in Yellowstone
Photo by NPS Neal Herbert
Watch Wildlife in Yellowstone's Lamar and Hayden Valleys
Yellowstone’s huge, wide valleys make excellent habitat for wildlife. For your best chance of spotting them, point your compass toward the Lamar and Hayden.
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Exit Northeast Entrance
Southeast Montana
Rest Stop:
Silver Gate Lodging Has the Closest Cabins to Yellowstone
A 1/2 mile from Yellowstone's northeast entrance, this quiet cabin resort is surrounded by snowcapped mountains and wildlife.
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Driving over Beartooth Pass
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Drive the Dramatic Beartooth Highway Northeast of Yellowstone
One of the most breathtaking routes to Yellowstone is the 68-mile stretch of the Beartooth Highway - named a National Scenic Byway’s “All-American Road.”
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Swords Rimrock Park
Courtesy Visit Billings
Top 7 Places to Find Food and Lore in Billings, Montana
Northeast of Yellowstone, find a brewery district, gluten-free pancakes and Old West charm in this city of 110,000.
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Montana elk grazing in early summer
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Lewistown, The Heart of Montana
From big game hunting to fishing, camping, biking, hiking and skiing, take advantage of the outdoor recreation opportunities in the beautiful Judith Basin.
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The Calvert Hotel
Photo courtesy of The Calvert Hotel
Have an Historic Stay at The Calvert Hotel
This historic building is beautifully remodeled to retain the classic design of the past while adding luxury amenities to provide the utmost in comfort.
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The Montana Bar in Miles City, Montana
Visit Southeast Montana
Southeast Montana is Cowboy Country
In search of the West before mocha lattes invaded corner cafes? You'll find it in these authentic towns.
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North Dakota
Badlands Formations
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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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