The Open Road Travel

Best Places To Stop On A Chicago To Yellowstone Road Trip

With a Chicago to Yellowstone road trip taking 21 hours, you will need to make a few overnight stops to make it enjoyable and manageable. There are a range of great places to do so, but the following two are easily the best.

Des Moines, Iowa

Des Moines is Iowa’s capital and most populous city. Not only does it feature one of the best selections of bars and restaurants you’ll encounter on the journey, but it also boasts several of the route's best attractions.

The Iowa State Capitol, built between 1871 and 1886, is the nation’s only five-dome Capitol building and a true sight to behold. The Kruidenier Trail Bridge is a stunning pedestrian walkway onto Grays Lake that offers panoramic views of the city and the surrounding area. The Greater Des Moines Botanical Garden is a 14-acre greenhouse displaying over 1,200 plant species from around the world, surrounded by beautiful works of art and water features.

Best Hotel To Stay At In Des Moines, Iowa - Staybridge Suites Des Moines Downtown by IHG

Staybridge Suites Des Moines Downtown by IHG is a 4-star hotel offering modern comfort and convenience in the heart of the city. Located along the Des Moines River, it provides spacious suites with full kitchens, flat-screen TVs, work desks, sofa beds, dining tables, air conditioning, and high-speed Wi-Fi.



Guests can enjoy complimentary hot breakfasts, evening social receptions, private parking, and amenities including a heated indoor pool and a fitness centre.

Keystone, South Dakota

Keystone, South Dakota, is a charming mountain town in the Black Hills known as the gateway to Mount Rushmore National Memorial. A quaint main street is lined with rustic shops, saloons, and restaurants, creating an Old West character. Attractions like the Big Thunder Gold Mine and museum, and the 1880 Train ride through the Black Hills to Hill City will entertain everyone from history buffs to nature lovers.

Keystone also offers easy access to outdoor adventure and breathtaking scenery. You can hike nearby trails, explore dramatic granite spires, take a scenic drive along Iron Mountain Road or Needles Highway, known for its tunnels and mountain vistas, or even take a helicopter ride over the whole area.

Best Hotel To Stay At In Keystone, South Dakota – Battle Creek Lodge

Battle Creek Lodge is a warm, inviting, family-run property in the heart of Keystone. Its friendly hospitality, cosy rooms, and peaceful atmosphere, surrounded by pine-covered hills, make it a memorable experience that turns most guests into repeat visitors. You can enjoy a complimentary breakfast each morning, chat with your hosts, relax on the spacious outdoor deck, and enjoy easy access to all of Keystone’s top attractions.



All rooms feature comfortable beds, private bathrooms, a flat-screen TV, a coffee pot, a hair dryer, air conditioning, and Wi-Fi, and free parking is available on site. The property also sells a selection of to-go food and drink to cater to all your needs.

Top Attractions On The Perfect Chicago To Yellowstone Road Trip

Davenport, Iowa

Davenport, Iowa’s 3^rd most populous city, lies on the banks of the Mississippi River. Best-known for its scenic riverwalk, which includes a stretch of the Mississippi River Trail, riverboat cruises and the River Music Experience are extremely popular, as is the revitalised downtown district and its local boutiques, restaurants, and breweries.



Other attractions include Vander Veer Botanical Park, the Figge Art Museum, with its American, Haitian, and Mexican Colonial art, and the Putnam Museum & Science Center’s planetarium and natural history and regional exhibits. Davenport also hosts many events throughout the year, including the Bix 7 Road Race, a seven-mile run honouring local jazz legend Bix Beiderbecke. 

Iowa 80 - World’s Largest Truck Stop

Iowa 80 – World’s Largest Truck Stop is a sprawling complex spanning over 75 acres. Serving more than 5,000 daily visitors, it features a huge convenience store, a food court with fast food staples, a 50s-style diner, a movie theatre, laundry facilities, showers, gift shops, a dentist’s office, a barber, a chiropractor, plenty of gas pumps, and the Iowa 80 Trucking Museum, which features a collection of vintage trucks and details the history of America's trucking industry.

Herbert Hoover National Historic Site

The Herbert Hoover National Historic Site, in West Branch, Iowa, is a preserved site detailing President Herbert Hoover's early years, rise to power, and enduring legacy. Centred around the modest two-room cottage where Herbert Hoover was born in 1874, it includes historically significant structures that demonstrate his simple, Quaker upbringing and life.

These include a replica of his father's blacksmith shop, his 1853 schoolhouse, the Friends Meetinghouse where his family worshipped, and the gravesite of President Hoover and his wife, Lou Henry Hoover. The Herbert Hoover Presidential Library and Museum displays informative exhibits covering his professional achievements and personal life.

Iowa City, Iowa

Iowa’s fifth-most populous municipality, Iowa City, is best known as the home of the University of Iowa and for being the United States’ only UNESCO City of Literature. Downtown Iowa City has independent shops, cafes, restaurants, and galleries. The Pedestrian Mall offers outdoor seating, public art, and regular live performances, and historic landmarks like the Old Capitol Building offer a glimpse into the city's political and architectural past.

Amana Colonies

The Amana Colonies are well-preserved, picturesque, mid-1800s Iowa villages built by German Pietists fleeing religious persecution. A registered National Historic Landmark, their communal kitchens, workshops, and homes demonstrate old-world charm, community, heritage, and craftsmanship.

Many original colonial structures now operate as businesses selling traditional German cuisine, local beer and wine, and handmade furniture and textiles. They also host seasonal festivals celebrating the colonies’ German roots, music, dancing, and food, such as Maifest and Oktoberfest.

Winterset, Iowa

Winterset, Iowa, is the setting of the novel “The Bridges of Madison County,” making it an ideal destination for fans of the book, its film adaptation, or historic covered bridges. Its main attraction, though, is the John Wayne Birthplace Museum. Located in the early 1900s house where “The Duke” was born and raised, its original décor and furnishings have been restored to demonstrate how he lived.



You will find a life-size statue of John Wayne out front, numerous artefacts and exhibits from his life and movies, a theatre screen showing a John Wayne documentary which can be watched on the original seats from Hollywood’s Chinese Theater, where many of his films premiered, and a wonderful gift shop selling John Wayne memorabilia. It is a can’t-miss destination for John Wayne fans.

Council Bluffs, Iowa

Council Bluffs, Iowa, is a historic city known for attractions such as the Union Pacific Railroad Museum, the Grenville M. Dodge House (the former home of a key figure in the construction of the Transcontinental Railroad), and the Squirrel Cage Jail (a three-story rotary jail that is now a museum). It is also home to Harrah’s Council Bluffs, one of the best casinos and poker rooms in the Great Plains.

The city also boasts a vibrant arts scene and hosts regular public art installations and cultural events. Lake Manawa State Park offers boating, fishing, and hiking, the 63-mile Wabash Trace Nature Trail is a scenic biking and walking route, and Tom Hanafan River's Edge Park features green spaces and trails with stunning views.

Omaha, Nebraska

Located just a 30-minute detour from our route, on the banks of the Missouri River, Omaha is Nebraska’s largest city and the second-largest in the Great Plains states, behind Oklahoma City. Founded in 1854, Omaha is known for its rich history, with over a dozen historic districts and more than 100 individual buildings listed on the National Register of Historic Places or as National Historic Landmarks. 

Sioux City, Iowa

Iowa’s fourth-most populous city, Sioux City, is a welcoming Midwestern destination on the Missouri River known for its history, culture, and scenic beauty. Downtown is alive with restored Art Deco architecture, local restaurants, and the Sioux City Public Museum, which details the region’s pioneer past. Other attractions include riverfront walking and biking trails, the Sioux City Art Center and its sculpture walk, and many unique festivals.

Sioux Falls, South Dakota

South Dakota’s largest, most populous city, Sioux Falls, sits on the banks of the Big Sioux River. Known for its amazing culinary institutions, parks, and open spaces, including Falls Park and the waterfalls the city is named after, it is recognised as the healthiest city in America.

Other attractions include galleries, markets, and exhibits carrying local artists’ work, unique sculptures and buildings, the Kirby Science Discovery Center, and the Great Plains Zoo & Delbridge Museum. Sioux Falls also has a large roster of annual festivals, including the SculptureWalk, Downtown Riverfest, SiouxperCon, First Fridays, Festival Of Bands, Sioux Empire Spectacular, and Party In The Park.



Dignity Of Earth And Sky

The Dignity of Earth and Sky is a stunning 50-foot stainless steel sculpture overlooking the Missouri River at a rest stop on I-90. Erected in 2016 by artist Dale Lamphere to honour the Lakota and Dakota people, it depicts a Native American woman holding a star quilt that symbolises respect, peace, and cultural heritage. 

Pierre, South Dakota

Pierre is South Dakota’s capital city and the nation’s second-smallest capital city, behind Montpelier, Vermont.



Set on the banks of the Missouri River, attractions like the elegant South Dakota State Capitol, the Cultural Heritage Center, which showcases the state’s Native American and pioneer heritage, LaFramboise Island Nature Area, the Oahe Dam and Lake Oahe, one of the United States’ largest reservoirs, and various historic buildings, combined with its inviting atmosphere, make it more than worth a visit, despite its size.

Wall Drug

Wall Drug is a historic, 76,000-square-foot shopping complex in the town of Wall known for its Wild West-style. Visitors can enjoy its famous ice water and find souvenir stores, eateries, the original 1931 drug store the complex is named after, an art gallery, and sculptures of historical and mythical creatures linked to the region, including a brontosaurus and a jackelope.



Badlands National Park

The 224,756-acre Badlands National Park was established on November 10^th, 1978, and receives 1.1 million annual visitors, making it the nation’s 38^th-oldest, 28^th-largest, and 25^th-most popular National Park.

A stunning area, filled with sprawling prairies and rugged canyons, it boasts one of the world’s best fossil collections. Resident palaeontologists will take you through the historic sights in great detail, while nature lovers have the chance to spot species including bison, bighorn sheep, and various deer and birds.

Bear Country USA

Bear Country USA is a fabulous, drive-through wildlife park, where visitors can see and interact with a massive selection of animals living freely in perfectly recreated habitats. The park's inhabitants include black bears, bison, elk, mountain lions, reindeer, numerous bird species, and more. It is an amazing stop for everyone, but especially for photographers and nature lovers.

Rapid City, South Dakota

South Dakota’s second-most populous city, Rapid City, is a wonderful destination with a vibrant culture named for its rapid expansion during the Black Hills Gold Rush. Its top attractions include Dinosaur Park, Storybook Island, the City of Presidents Walking Tour, the Journey Museum and Learning Center, and Reptile Gardens.

Rapid City is also a perfect base for exploring the countless attractions in the surrounding area, and even those further afield, such as the site of the infamous Wounded Knee Massacre just 90 minutes away.

Wind Cave National Park

Wind Cave National Park was established on January 9^th, 1903, and gets 490,000 annual visitors, making it the nation's 6^th-oldest and 24^th-least visited National Park. At 33,970 acres, it ranks as the 12^th-smallest National Park in the United States, but, below ground, it features one of the world’s longest (6^th), most complex cave systems.

Known for its fabulous boxwork and frostwork formations, it is named for the winds that occur in the cave as the air pressure fluctuates. While cave tours let you appreciate its formations and various bat species and other inhabitants, exploration above ground reveals dense pine forests, sprawling, grassy prairies, and animals such as bison, cougars, elk, ferrets, prairie dogs, and numerous bird species.

Mount Rushmore National Monument

Mount Rushmore National Monument is one of the world’s most iconic monuments. Constructed from 1927 to 1941 by Gutzon and Lincoln Borglum, it features the faces of four former U.S. presidents. George Washington, Thomas Jefferson, Theodore Roosevelt, and Abraham Lincoln were chosen to represent the nation’s birth, growth, development, and preservation.



Combined with its scenic surroundings, Mount Rushmore is an incredible work of art and an experience unlike virtually anything else on Earth. 

Black Hills National Forest

The 1.25-million-acre Black Hills National Forest stretches across the Black Hills of South Dakota. A sprawling wilderness filled with pine trees, towering mountains, hiking trails, scenic highways, breathtaking vistas, wildlife, and other iconic sights, it is a natural destination with attractions for everyone to enjoy.

It has so much to offer that we even published a Black Hills National Forest Guide that you can read here.



Crazy Horse Memorial

The Crazy Horse Memorial is a monument on Thunderhead Mountain depicting Oglala Lakota warrior Crazy Horse, which has been under construction since 1948. It will be the world’s second-tallest statue upon completion, with the head dwarfing those on nearby Mount Rushmore.

Despite being far from complete, it provides the chance to see how monuments of this size are created, learn about Crazy Horse and the Lakota people, and even grab a free souvenir, as visitors are gifted a piece of the mountain removed during construction.

Sturgis, South Dakota

Sturgis is a small town filled with a vibrant atmosphere and culture. It is best known for the Sturgis Bike Week Festival, which occurs the first week of August each year. First held in 1938, upwards of half a million people come to enjoy live music, entertainment, local cuisine, and scenic rides through the Black Hills. There is even the Sturgis Motorcycle Museum & Hall of Fame, where you can enjoy the culture and history year-round.



Deadwood, South Dakota

Deadwood is the second-largest Wild West town still in existence, behind only Tombstone, Arizona. Historical Markers litter the streets and highlight events that occurred there, such as the 1876 murder of Wild Bill Hickok. An important city during the Black Hills Gold Rush, it has been home to many famous names through the years, including Wyatt Earp and Calamity Jane. It now boasts everything from historic attractions to casinos.

For an in-depth analysis, read our Deadwood guide here.

Geographic Centre Of The Nation

The Geographic Centre of the Nation is a monument signifying the central point of all 50 U.S. states after Alaska and Hawaii joined the Union in 1959. While the exact spot lies about 20 miles north on private land, the monument was erected in Belle Fourche, South Dakota, to make it accessible to visitors. It features a large granite compass rose, U.S. flag, and historical markers explaining the site’s significance.



Surrounded by a small park, it is also near the Tri-State Museum, which showcases local history and artefacts.

Devils Tower

The Devil’s Tower is one of the world’s most iconic buttes and the United States’ first National Monument, having been designated in September 1906 by President Theodore Roosevelt. Standing 867 feet tall, it is present in numerous Native American legends, movies, and works of art, and is a unique attraction you can’t miss when travelling through Wyoming.

Thunder Basin National Grassland

Thunder Basin National Grassland is among the largest grasslands in the US, at over 500,000 acres. Its wide-open prairies are part of what earned Wyoming the nickname “cowboy country”. Used by both conservationists and ranchers, they are home to wildlife such as badgers, bats, black-tailed prairie dogs, cotton-tails, coyotes, deer, foxes, jackrabbits, pronghorn, rats, squirrels, and more than 100 species of birds.



Bighorn National Forest

The 1.1-million-acre Bighorn National Forest sits over 5,000 feet up in the Bighorn Mountains and preserves some of the oldest protected forests in the United States. Known for its stunning views and wilderness areas, it is also home to the Medicine Wheel National Historic Landmark. An 80-foot-wide, white limestone monument and sacred Native American ceremonial site, it dates back over 10,000 years and is still used today.

Cody, Wyoming

Named after the legendary Colonel William “Buffalo Bill” Cody, Cody, Wyoming, is known as the “Rodeo Capital Of The World”. In the summer, the Cody Night Rodeo takes place nightly, and the United States’ largest rodeo, the Cody Stampede Rodeo, is held over the 4^th of July weekend.

One of the United States’ best remaining Wild West towns, Cody is also home to the Buffalo Bill Centre of the West museum complex. Deemed the most comprehensive museum complex dedicated to the Old West and listed among America’s most remarkable museums, it is a must-visit for anyone interested in Cowboy culture or local history.

Final Thoughts On A Perfect Chicago To Yellowstone Road Trip Itinerary

This concludes our guide to planning a perfect Chicago to Yellowstone road trip itinerary. You should’ve now decided when to travel, which route to use, where to stay, and what to see on the drive. We also have a Yellowstone National Park guide to help plan your time in the park, which you can read here.



All that’s left is to decide what to take with you, and then you can start booking and budgeting everything, so you can look forward to enjoying it all for yourself as soon as possible. Anyone looking to continue their journey may also appreciate our guide to a road trip from Yellowstone to Grand Canyon, which you can read here.