Home Road Trips Forget Route 66 – Take This Epic Chicago to Denver Road Trip Instead

Forget Route 66 – Take This Epic Chicago to Denver Road Trip Instead


Want to see the best of the Midwest? This Chicago-to-Denver road trip is more scenic than Route 66, and it hits many of the highlights from the Windy City to Rocky Mountains, and much more.

Many travelers dream of driving a legendary cross-country road trip or following the storied Route 66, but a Chicago to Denver trek offers a solid mix of natural wonders, small-town America and big city nightlife. There’s something for everyone on this journey.

Route 66 dips into the Southwest and takes you through such locations as Oklahoma City and Santa Fe on a mostly diagonal path to the Pacific Ocean. However, the button-hook drive we’re proposing here will show you a much different cross-section of America.

First thigs first: Why start your road trip in Chicago? Besides being an easy city to fly into from almost anywhere in America, Chicago is also a fun, friendly town with some of the best bars and restaurants in the country.

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Looking for day trip ideas from Chicago instead? Here’s Nine Fantastic Day Trips from Chicago.

If you’re a sports fan, you’ve got to make a pilgrimage to Chicago. They love professional sports here, especially the Chicago Bulls and Chicago Blackhawks during the winter. When the boys of summer are in swing, you can head to Wrigleyville to catch the Chicago Cubs in action. The Cubbies won their first World Series since 1907 in the fall of 2016, ending baseball’s longest championship drought.

Chicago, Illinois skyline

Chicago, Illinois skyline on June 7, 2018.

Meanwhile, there’s a diverse cross-section of nightlife in Chicago, ranging from Piano Bars to Dive bars to night clubs, all within walking distance of each other in many cases. Cover charges are rare in Chicago, and many spots stay open until 4 am. A late last call is either a feature or a bug, depending upon your enthusiasm for a night on the town.

Once you shake off your hangover, it’s time to hit the road. Interstate 90 is your best bet to head west out of town, but before you start moving north toward Minneapolis, chart a course for Dubuque, Iowa on Route 20 where you’ll cross the Mississippi River in about 3.5 hours.

Shortly thereafter, if you’re willing to “go the distance,” you’ll come upon Dyersville, Iowa, home to the Field of Dreams Movie Set. Here you can pay homage to the 1989 Kevin Costner classic and take a few swings for the cornfields on the very same diamond that the 1919 Black Sox “returned” for redemption from their baseball banishment. Even if you’ve never seen Field of Dreams, if you like baseball, this is a definite must-see.

Baseball fans come from all over the country to see this legendary location. The diamond is well maintained, and you’ll usually find other tourists on hand ready to have a catch. Over 65,000 fans visit the landmark every year.

Des Moines is probably a good place to call it a night, with plenty of restaurant and hotel options. Just over 200,000 people call Des Moines home, and U.S. News ranked it the 11th best place to live in the country.

The Des Moines Capitol Building is pretty iconic, as it’s the only five-domed capitol in the nation. So you can check that off your list.

For Day 2, you can either press westward onto nearby Omaha, or dip south and stop in for some barbecue in Kansas City before heading back north along the Nebraska border and Missouri River up I-29. You’ll pass through Sioux City, IA, which borders both South Dakota and Nebraska. Further north, just before you rejoin Interstate 90, you’ll hit Sioux Falls, South Dakota. The falls, situated on the Big Sioux River, are worth a stop. While the falls aren’t dramatic in terms of their vertical drop, the Falls Park covers 123 acres and 7,400 gallons of water drop every second over the course of the falls.

You’ll notice the landscape starting to change as you head into South Dakota. But before you get to the Badlands, you’ll have to stop in for a piece of Americana (and perhaps some popcorn) at the World’s Only Corn Palace in Mitchell, SD. About 70 miles west of Sioux Falls, The World’s Only Corn Palace is a quick detour off I-90.

Badlands National Park in South Dakota

Badlands National Park in South Dakota

Badlands National Park is next, and it is spectacular. Set on nearly a quarter-million acres in southwestern South Dakota, the Badlands contains one of the richest fossil beds on the planet. Bison, big horn sheep and prairie dogs roam these lands of buttes, sod tables and clastic dikes. There’s nearly a million years of history here, and it’s etched upon the rock formations. But erosion is slowly eating away at them, and scientists estimate that in the next 500,000 years, they’ll have totally eroded. As the official Badlands National Park website jokes, come visit them while you still can!

Next up, head for the Black Hills, where you’ll find a few familiar faces. Four of them, in fact. Mount Rushmore is situated in Keystone, South Dakota, where the 60-foot faces of Abraham Lincoln, George Washington, Thomas Jefferson and Theodore Roosevelt are carved into the side of a mountain.

Nearby in Custer County, you’ll find the Crazy Horse Memorial, the world’s largest mountain carving, albeit a carving that’s far from complete. The controversial monument has been under construction since 1948, with seemingly no end in sight. The finished version is expected to be 641 feet long and 563 feet high, depicting the Native American warrior Crazy Horse atop his steed. The ongoing drama surrounding the ambitious monument project is fascinating.

North of Custer is Deadwood, SD, a gold rush town from the late 1870s that attracted such Wild West legends as Wyatt Earp, Calamity Jane and Wild Bill Hickok. Deadwood was reintroduced into popular culture by the eponymous HBO series in the mid-2000s.

As you cross the border into Wyoming, Devils Tower is next on the agenda. Visible from miles away on clear day, Devils Tower rises 867 feet above its base. The stone monolith, considered sacred by several Plains tribes, was made famous by its inclusion in the 1977 film, Close Encounters of the Third Kind.

Across Wyoming sit two incredible National Parks, Grand Teton National Park, and perhaps the most famous of them all, Yellowstone National Park. While you could head due west on state routes to access the parks, if you’re more comfortable with divided-highway Interstate driving, keep following 90 up into Montana, and swing through Billings and Bozeman to make an approach from the north. You’ll also enjoy some spectacular scenery throughout the drive in Montana.

Grand Prismatic Spring, Yellowstone National Park

Grand Prismatic Spring, Yellowstone National Park in Wyoming

Yellowstone is one of the five best National Parks in America, as it offers various thermal attractions, most notably Old Faithful and the Grand Prismatic Spring, while Grand Teton features iconic mountain sunsets and String Lake, as well as skiing and golf at nearby resorts.

Outside the parks, Idaho awaits, where you’ll find the Snake River, Idaho Falls and Craters of the Moon National Monument. Craters of the Moon is a massive lava field suitable for hiking and camping in other-worldly landscapes. It’s a bit off the beaten path, but also a memorable destination just south of Arco, Idaho.

After your swing through Idaho, head south for Salt Lake City, and explore Antelope Island State Park, where bison roam free. (Keep your distance. They’re dangerous.) Check out the history of the Mormon Church downtown, or head east through the mountains to Park City, one of the world’s premier skiing and resort towns.

Balanced Rock at Arches National Park

Balanced Rock at Arches National Park in Moab, Utah. Photo by Peter Stringer

You’re in the home stretch now. It’s time to make tracks for Moab, home of Canyonlands National Park, Arches National Park, and Dead Horse Point State Park. All three are worth visiting, but Arches is the most impressive of the three, and typically ranks among the top five National Parks in America. Capitol Reef National Park and Bryce Canyon National Park are also within a few hours distance, but you’d need several days in Eastern Utah to hit them all and do these parks justice. If you can’t find reasonable accommodations in Moab, 100 miles away in Grand Junction you’re likely to find more plentiful options.

As you head into Colorado for the last leg of the trip, if you follow I-70 you’ll be within striking distance of the Coors Brewing factory on your way to Denver. Otherwise, if you want to add Rocky Mountain National Park to your itinerary, you’ll have to head a little out of your way, as the park sits northwest of the city.

As for Denver, whether you want to visit the legendary Red Rocks concert venue, experience the night life on 16th Street, or catch a Rockies game at Coors Field, there’s plenty of fun to be had in the Mile High City.

Photo Gallery:

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This time, it's OK to leave a trace (Review)

Rated 5 out of 5

Looks like a great trip!

I wish it included how many days you could expect a trip like this would take.

I know you can add days with all the sights to see but a general idea would be helpful.

Submitted by
Deborah Tulley
May 26, 2022
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