The Best Road Trip From Chicago to Yellowstone National Park

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  • Chicago, IL to Rochester, MN
  • Rochester, MN to Keystone, SD
  • Keystone, SD to Yellowstone
  • Roadside assistance
  • Cheap car insurance
A road trip from the Windy City to America’s first national park will expand your horizons as you explore the intersections between natural wonders and man-made treasures.
Breaking up this 1,500-mile trip into three days will allow you to visit must-see locations, including the majestic Mount Rushmore. We also recommend that you make some stops along the way in Madison, Rochester, Sioux Falls, Keystone, and Casper before you reach Yellowstone National Park. This will allow you to experience both urban delights and breathtaking scenery.
With a long road trip ahead, make sure you’ve got the car insurance protection you need. The licensed insurance broker app Jerry will help you find the cheapest quote for your insurance needs in under a minute.
And don’t stress about the potential for a flat tire in the wild—Jerry has you covered with their emergency roadside assistance program. With emergency assistance, vehicle towing, and more, you won’t have to worry about any unexpected hiccups along your journey.
This road trip from Chicago to Yellowstone National Park will inspire you to put down your phone and marvel at the glories of the West.
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Day one: Chicago to Rochester

Driving time: 5.5 hours
On the first (and shortest) day of your road trip, you’ll depart from Chicago, Illinois and head northwest toward the state capital of Wisconsin. Madison’s lakefront views, historical landmarks, and vibrant culture make it the perfect stop for lunch and sightseeing.
Crowded Chicago buildings glitter over a major roadway at sunset.
Chicago, Illinois

Stop in Madison, WI

Must do: Experience the “Condimental Divide” at the National Mustard Museum, where mustard lovers leave ketchup loyalists behind to peruse over 6,000 types of mustard. View mustard artifacts and sample hundreds of mustards at the Tasting Bar.
Must see: Visit the Herbert Jacobs House, also known as “Jacobs I,” Frank Lloyd Wright’s first “Usonian” structure—the prototype for an affordable architecture that harmonized with the American landscape. Although the home is privately owned, tours are available by appointment.
Must eat: Eat lunch at one of Madison’s “Streateries,” where outdoor dining meets urban sightseeing. Try Dotty Dumpling’s Dowry, a favorite among Madison locals in the heart of downtown that has been voted “Best Burger in Madison” for over 40 years in a row.
A view of the Wisconsin State Capitol Building dome against a blue sky.
Madison, Wisconsin

Stay in Rochester, MN

After a little over three hours in the car, you’ll arrive in Rochester, Minnesota, home of the Mayo Clinic and a major IBM facility. With a vibrant art, music, and craft beer scene, Rochester is worth an overnight stay.
Must do: Take in Rochester’s lush natural scenery at the Quarry Hill Nature Center, where you can choose between hiking or biking the trails, fossil hunting at the limestone quarry, and exploring historic sandstone caves.
Must see: Visit the Rochester Art Center, where you can enjoy interactive exhibits and an ever-revolving collection of contemporary art. Located on the banks of the Zumbro River, the Rochester Art Center is as stunning outside as it is inside—and while outside, experience the “Circumcenter” sculpture that translates typed wishes into braille and then into musical notes.
Must eat: Grab dinner at The Tap House, where you can cozy up next to a large fireplace on the rooftop patio. Enjoy one of The Tap House’s mouthwatering burgers, wraps, or sandwiches while drinking one of the 50-plus beers on tap.
Where to stay: Consider turning in at the Kahler Grand Hotel, a long-time favorite of travelers that connects directly to the Mayo Clinic and other downtown businesses through climate-controlled skyways and pedestrian subways.
Dark water tumbles down a waterfall on a cloudy day in Rochester, Minnesota.
Rochester, Minnesota

Day two: Rochester to Keystone

Driving time: 9 hours
On the second day of your road trip, you’ll leave charming Minnesota and head out west to two South Dakota cities.

Stop in Sioux Falls, SD

The largest city in South Dakota, Sioux Falls, is known for its eclectic culinary experiences, natural wonders, and dynamic downtown.
Must do: At the Butterfly House and Aquarium, you can surround yourself with over 800 free-flying butterflies from all around the world. As South Dakota’s only public saltwater aquarium, this destination offers opportunities to pet stingrays and sharks, view coral reefs, and touch unique invertebrates in the Pacific Tide Pool.
Must see: You can’t pass through Sioux Falls without exploring Falls Park, after which the city is named. Watch approximately 7,400 gallons of water plummet 100 feet over the Falls each second from the five-story observation tower or one of the many viewing platforms.
Must eat: If you’re in the mood for fine dining, try Minervas, an iconic restaurant in downtown Sioux Falls. Enjoy a hand-cut steak, fresh salad, seafood plate, or pasta dish before strolling around the city’s SculptureWalk, where a rotating collection of sculptures line the walkways to downtown restaurants and stores.
A series of small waterfalls at Sioux Falls sits in front of a bridge. On the right, tourists look at the scene.
Sioux Falls, South Dakota

Stay in Keystone, SD

Pack in as much fun in Sioux Falls as you can before getting back in the car for a five-hour trek to Keystone, a scenic South Dakota city tucked in the heart of the Black Hills.
Must do: Ready to let loose after a long day in the car? Rushmore Tramway Adventures is an adventure park with numerous attractions, including a zipline, alpine slide, aerial adventure park, tubing hill, scenic chairlift, and more.
Must see: Now’s your chance to visit Mount Rushmore National Memorial, where the faces of George Washington, Thomas Jefferson, Theodore Roosevelt, and Abraham Lincoln are carved 60-feet high into the granite side of the Black Hills mountains. Learn the history of this colossal sculpture at the museum’s interactive exhibits.
Must eat: Grab a pizza or calzone at Cruizzers, a Traveler’s Choice-award-winning pizzeria with indoor and outdoor seating.
Where to stay: If you’re visiting Keystone between mid-April to October, stay at the seasonal hotel K Bar S Lodge, located at the foot of the Black Hill Mountains. With close proximity to many local attractions, spacious rooms, and breathtaking views, K Bar S Lodge promises a memorable overnight stay.
The stone presidential portraits at Mount Rushmore National Memorial seen from below.
Mount Rushmore National Memorial, South Dakota
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Day three: Keystone to Yellowstone National Park

Driving time: 9 hours
On the last leg of the three-day road trip, you’ll depart from South Dakota and make your way to Wyoming. With another nine hours planned in the car today, you’ll want to leave early enough to enjoy a mid-trip excursion in Casper.

Stop in Casper, WY

A nature-oriented city with a bustling downtown, Casper offers something for everyone to enjoy. Nicknamed “The Oil City,” Casper is one of the few locations where the historic Oregon, Mormon, California, and Pony Express trails converge.
Must do: Enjoy free admission to the National Historic Trails Interpretive Center, where you can learn about the historic trails along which early pioneers traveled. With eight galleries and several temporary exhibits, the Trails Center provides rich context into the experiences of emigrants in the American West.
Must see: Visit the Tate Geological Museum, which houses over 3,000 fossils and minerals. Enjoy the dinosaur fossils, Dee the Mammoth (an 11,600-year-old mammoth from the Ice Age), and the giant bronze T. Rex replica. The Tate delivers an educational and exciting museum experience.
Must eat: Stop for lunch at Johnny J’s Diner, an authentic fifties diner with a soda fountain counter. Enjoy the retro vibe as you eat reasonably-priced yet high-quality diner fare.
A row of blue metallic sculptures leads to the National Historic Trails Interpretive Center.
National Historic Trails Interpretive Center

Stay in Yellowstone National Park

A final five-hour stretch will bring you to your destination, Yellowstone National Park, a 3,500-square-foot wilderness recreation area situated on a volcanic hot spot. Spread across three states (Wyoming, Idaho, and Montana), Yellowstone is famous for its sublime canyons, geysers, hot springs, forests, and alpine rivers.
Must do: Journey to the Idaho side of Yellowstone National Park to drive through Yellowstone Bear World. From the comfort of your car, you can spot grizzly and black bears, bison, elk, moose, mountain goats, and other animals roaming free on the land. Other attractions include a petting zoo, educational exhibits, and amusement rides.
Must see: Make sure to see the star of Yellowstone—Old Faithful, an erratic geyser whose eruptions (about 20 per day) can soar 180 feet high. With water reaching temperatures of 204 degrees Fahrenheit and steam above 350 degrees Fahrenheit, this natural wonder is enjoyed from a safe distance at the geyser-viewing area.
Must eat: When visiting Yellowstone, it’s a must to dine at the Old Faithful Geyser Grill in the Old Faithful Inn, the largest log structure in the world. Originally built between 1903 and 1904, the inn serves breakfast and lunch first come, first serve, and dinner by reservation.
Where to stay: Since you’ll be dining at the Old Faithful Geyser Grill, why not also stay at the Old Faithful Inn, a national historic landmark whose rooms blend modern furnishings with rustic charm.
A tower of steam rises at Old Faithful, creating a rainbow against the blue sky.
Old Faithful, Yellowstone National Park

Why you need roadside assistance

When you’re spending over 23 hours in the car while traveling across five states, the last thing you want is a roadside emergency to disrupt your journey. Jerry is here to help you get to your destination with ease, safety, and confidence. Jerry’s roadside assistance program features jumpstarts, tire changes, and lockout assistance.
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