The Best Road Trip From Chicago to Yellowstone National Park

This three-day road trip from Chicago to Yellowstone National Park takes you to the best museums, nature centers, and attractions of the American West.
Written by Jennifer Yirinec
Reviewed by Carrie Adkins
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
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.
Let Jerry find your price in only 45 seconds
No spam · No long forms · No fees
Find insurance savings

Key trip details

Chicago to Yellowstone National Park
Distance: 1,462 miles
Driving time: 22 hours and 51 minutes
Suggested length of trip: 4 to 7 days


  • Madison, WI
  • Rochester, MN
  • Sioux Falls, SD
  • Keystone, SD
  • Casper, WY
  • Yellowstone National Park

Chicago to Madison

147 miles, 2 hours 20 minutes
On the first (and shortest) day of your road trip, you’ll depart from Chicago,
and head northwest toward the state capital of
. Madison’s lakefront views, historical landmarks, and vibrant culture make it the perfect stop for lunch and sightseeing.
Take I-90 W to get to Madison.

Where to eat in Madison

  • Dotty Dumpling’s Dowry
    ($$): 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.

What to do in Madison

Downtown Madison
  • National Mustard Museum
    : 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.
  • Herbert Jacobs House
    : 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.

Madison to Rochester, MN

210 miles, 3 hours 27 minutes
After a little over three hours in the car, you’ll arrive in Rochester,
, 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.
For Rochester, get back onto I-90 W.

Where to eat in Rochester

  • The Tap House
    ($$): 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.

What to do in Rochester

Peace Plaza, Rochester
  • Quarry Hill Nature Center
    : 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.
  • Rochester Art Center
    : 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.

Where to stay in Rochester

  • Kahler Grand Hotel
    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. Cost per night: from $103

Rochester to Sioux Falls

243 miles, 3 hours 56 minutes
The largest city in
South Dakota
, Sioux Falls, is known for its eclectic culinary experiences, natural wonders, and dynamic downtown.
You’re headed back onto I-90 W to get to Sioux Falls.

Where to eat in Sioux Falls

  • Minervas
    ($$$): 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
    , where a rotating collection of sculptures line the walkways to downtown restaurants and stores.

What to do in Sioux Falls

Sioux Falls Park
  • Butterfly House and Aquarium
    : 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.
  • Falls Park
    : 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.

Sioux Falls to Keystone, SD

367 miles, 5 hours 15 minutes
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.
You guessed it, you’re headed back onto I-90 W for Keystone.

Where to eat in Keystone

  • Powder House Lodge
    : For a cozy wood-paneled interior, hit up the Powder House Lodge for American specialties and sweet views.
  • Cruizzers
    : Grab a pizza or calzone at Cruizzers, a Traveler’s Choice-award-winning pizzeria with indoor and outdoor seating.

What to do in Keystone

Mount Rushmore National Memorial
  • Rushmore Tramway Adventures
    : 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.
  • Mount Rushmore National Memorial
    : 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.

Where to stay in Keystone

  • K Bar S Lodge
    : 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. Cost per night: from $116
Let Jerry find your price in only 45 seconds
No spam · No long forms · No fees
Find insurance savings

Keystone to Casper, WY

237 miles, 3 hours 50 minutes
On the last leg of the three-day road trip, you’ll depart from
South Dakota
and make your way to
. With another nine hours planned in the car today, you’ll want to leave early enough to enjoy a mid-trip excursion in Casper.
For Casper, take US-18 W and then I-25 N.

Where to eat in Casper, WY

  • Johnny J’s Diner
    ($$): 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.

What to do in Casper

National Historic Trails Interpretive Center
  • National Historic Trails Interpretive Center
    : 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.
  • Tate Geological Museum
    : 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.

Casper to Yellowstone National Park

268 miles, 4 hours 30 minutes
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 (
, and
), Yellowstone is famous for its sublime canyons, geysers, hot springs, forests, and alpine rivers.
Get to Yellowstone from Casper via US-20 W and WY-120 W.

Where to eat in Yellowstone

  • Old Faithful Geyser Grill
    : 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.

What to do in Yellowstone

Old Faithful
  • Yellowstone Bear World
    : 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.
  • Old Faithful
    : 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.

Where to stay in Yellowstone

  • Old Faithful Inn
    : 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.

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.
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.
Next time you hit the road, make sure you are fully prepared with Jerry’s roadside assistance program membership.

Finding affordable car insurance

Don’t leave home without ensuring you have the protection you need for your car or rental vehicle.
can find you
cheap car insurance
with the best coverage in under a minute.
Drivers who use Jerry’s AI-based insurance broker app save an average of $879 a year! And the best part...Jerry is completely free to use. So what are you waiting for? Download the Jerry app now and get competitive quotes in under a minute.
"I went into the app thinking I wouldn’t change my insurance, but boy was I wrong! I received a quote for half of what I was paying and was able to add roadside assistance at the same time. I’m so glad I gave this a try!"—Satisfied Jerry user
Haven’t shopped for insurance in the last six months? There might be hundreds $$$ in savings waiting for you.
Judith switched to Progressive
icon savingsSaved $725 annually
Alexander switched to Travelers
icon savingsSaved $834 annually
Annie switched to Nationwide
icon savingsSaved $668 annually
Are you overpaying for car insurance?
Compare quotes and find out in 45 seconds.
Try Jerry

Easiest way to compare and buy car insurance

No long forms
No spam or unwanted phone calls
Quotes from top insurance companies
Find insurance savings