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The Road Trip of a Lifetime: Chicago to LA

Destinations You Don’t Want to Miss When Driving Cross-Country From Chi-Town to the City of Angels.

With over two thousand miles between Chicago and Los Angeles, driving from one city to the other might seem like too ambitious of a road trip, even for a seasoned traveler. Well, toss those pessimistic notions aside—because we’re here to tell you that not only can it be done, but it should be done! That’s right, we’re saying that a cross-country drive from Chi-Town to LA is absolutely worth it. Sure, it might take a bit of planning, but luckily for you, we’re here to help. 

Traveling from Chicago to LA by car means passing through multiple states and a number of cities—which means that there’s a long list of destinations to choose from when planning your road trip. Of course, there’s no right or wrong answer when it comes to picking out points of interest to stop as you’re driving from one place to the next, and what sounds good to one person might not seem so great to someone else. But even so, we think these nine stops on the way from Chicago to the City of Angels are definitely road trip material! 


John and Mary Pappajohn Sculpture Park 

📍 Des Moines

Outdoor Artwork in Downtown Des Moines

1330 Grand Avenue | Downtown | www.desmoinesartcenter.org

First up on our list of detours is Des Moines, Iowa’s state capital and the home of the Iowa State Fair. Des Moines is about five hours from Chicago, so it makes for an ideal stopping point after your first day of driving. Some of Des Moines’ top attractions include Blank Park Zoo, the Greater Des Moines Botanical Garden, and, of course, the Iowa State Capitol Building. But before you hit the road again, be sure to check out the John and Mary Pappajohn Sculpture Park in the Downtown area. 

The park’s four and a half acres of green space serve as a backdrop to an array of sculptures, which can be viewed from sunrise to sunset, no admission cost required! You probably know John Pappajohn, a longtime Des Moines resident, for his pizza, but after a visit to this delightfully engaging park, you’ll remember him for his commitment to giving back to the city of Des Moines. 

Harold Warp Pioneer Village 

One of the Most Extensive Collections of Americana 

📍 Minden (NE)

138 E. U.S. Highway 6 | Minden | www.pioneervillage.org

History buffs, antiquers, and anyone else who enjoys a hidden gem of a roadside attraction is sure to be amazed by the Harold Warp Pioneer Village, a museum that has thousands of American historical, industrial, and cultural artifacts, most of which are arranged in chronological order. Spanning 20 acres and 26 buildings, Pioneer Village offers visitors a diverse, detailed look at American history over the many years of its development. 

From transportation and homemaking to agriculture and communication, the exhibits at Pioneer Village depict how different sectors of American life have evolved with time and the release of new technologies. In addition to relics and collectibles, Pioneer Village also showcases a number of preserved and restored buildings, including a railroad depot and a general store. You can also visit old-time businesses and shops like a doctor’s office, print shop, cobbler shop, drugstore, and barbershop. 

Red Rocks Park and Amphitheater

📍 Denver

See a Place Where Dinosaurs Once Walked and the Musical Legends Continue to Perform 

18300 W. Alameda Parkway | Morrison | www.redrocksonline.com

Colorado’s capital is becoming an increasingly popular travel destination, and once you experience it for yourself, you won’t have any trouble seeing why. While Denver has plenty to see and do, there’s one spot that lies a little outside of the city that’s especially worth penciling into your itinerary: Red Rocks Park and Amphitheater. About a half-hour drive from Downtown Denver, Red Rocks is both a park and concert venue that has been charming visitors since its opening in 1941. The park embodies an intersection between the Great Plains and the Rocky Mountains, and it boasts the only naturally-occurring and acoustically perfect amphitheater in the world. 

Ship Rock and Creation Rock are the two three-hundred-foot monoliths that form Red Rocks Amphitheater, which has served as a stage for big names like the Beatles, Jimi Hendrix,  the Grateful Dead, U2, Radiohead, Daft Punk, and many, many more. You might not be in town for a concert, but you can still explore the park and admire its cultural and historical significance as well as its natural beauty. There’s even a restaurant where you can enjoy a quality meal while overlooking the park, plus a gift shop where you can get souvenirs and gifts to commemorate the experience

Dinosaur Journey Museum 

📍 Fruita (CO)

Venture Deep into the Heart of Dinosaur Country 

550 Jurassic Court | Fruita | www.museumofwesternco.com

Fruita, Colorado, is around four hours from Denver and is considered a central point in Colorado’s “Dinosaur Country.” Learn more about western Colorado’s dino-filled history when you make a trip to Dinosaur Journey Museum, an institution that houses over 15 thousand fossils! Marvel at the region’s prehistoric ancestors when you come face to face with skeletal casts and robotic reconstructions of the reptilian residents that once occupied this part of Colorado and its surrounding area. 

In addition to exhibits and displays, you can also get an up-close look at a genuine paleontology lab where fossils are prepared before being put out in the museum, and there’s even a pretend quarry site where aspiring dinosaur experts can dig up Jurassic remains of their own. Other interactive features of the museum include an earthquake simulator, a sandbox for making dino tracks, and a reading library with more info about the giants that once roamed Colorado. 

Mystic Hot Springs

📍 Monroe (UT)

A One-of-a-Kind Place to Spend the Night 

 475 E. 100 N. | Monroe | www.mystichotsprings.com

Looking for a place to stay the night when passing through Monroe, Utah? Try booking a stay at Mystic Hot Springs, a resort and campsite with natural hot springs that hover around 100 degrees Fahrenheit. Overnight options at Mystic Hot Springs include guesthouse rooms, pioneer cabins, tents and RVs, and even converted school buses. While certainly not a lavish hotel, Mystic Hot Springs is a novel experience that you’ll never forget. 

As it turns out, the titular hot springs are just as popular today as they were years and years ago when Ute, Shoshone, or Piute tribes occupied the area. Similarly, the springs were a frequented resting place for settlers passing through what’s now Monroe. While some visitors describe Mystic Hot Springs as a time warp transporting them back to the 1960s and 70s, the resort is very careful to maintain a welcoming environment that’s conducive to visitors of all ages—which means no alcohol, nudity, or smoking and quiet hours from 9 pm until 9 am. 

Fremont Street Experience 

📍 Las Vegas

They Don’t Call It the “City of Lights” For Nothing! 

Fremont Street | Downtown | www.vegasexperience.com 

You can’t pass through southern Nevada without making a stop in Sin City, especially if you’re on a road trip. During your time in Vegas, you don’t want to miss out on the Fremont Street Experience, the seven-block pedestrian mall and entertainment district in Downtown Vegas. From restaurants and shopping to live music and rides, you can find attractions of every kind on Fremont Street, and there are countless more that you can find within walking distance. 

If there’s one thing that you have to see on Fremont Street, it’s the Viva Vision Light Show, commended as one of the best (and only) free things to do in Las Vegas. Watch musical performances from some of the best-known bands and artists as they’re broadcasted on one of the largest video screens in the entire world. Shows start hourly and are open to the public, no admission necessary. 

Death Valley National Park 

📍 Lone Pine (CA)

Massive Desert Wonderland 

328 Greenland Boulevard | Death Valley | www.nps.gov

At 3.4 million acres, Death Valley National Park is the largest national park in the contiguous U.S. Vast valleys, rocky canyons, majestic mountains, and desert wilderness are all geological features that are found in Death Valley. From sand dunes and salt flats to wetlands and oases, the geography in Death Valley is as incomprehensibly versatile as it is visually stunning. Despite its largely arid appearance, Death Valley provides habitats to a variety of wildlife including bighorn sheep, kangaroo rats, desert tortoises, coyotes, jackrabbits, lizards, hawks, and swallows. 

Among the most noteworthy spots in the park is Badwater Basin, a salt flat that sits at the lowest elevation in North America. Other popular points of interest are Artists Drive, Devils Golf Course, Golden Canyon, and Zabriskie Point. Like most national parks, Death Valley is host to an assortment of outdoor activities like hiking, biking, camping, backpacking, and stargazing. You might look around the park and think that it looks almost otherworldly—and as it turns out, the makers of Star Wars thought the same thing! Star Wars: Episode IV — A New Hope and Star Wars: Episode VI — Return of the Jedi both feature scenes filmed in Death Valley. 

Elmer’s Bottle Tree Ranch 

📍 Oro Grande (CA)

A Route 66 Favorite

24266 National Trails Highway | Oro Grande | www.thebottletreeranch.com

This roadside treasure along Route 66 is a shining example of the unexpected—and unusual—sights that are just waiting to be discovered by wanderlust-fueled road-trippers. Elmer’s Bottle Tree Ranch is a collection of outdoor assemblage sculptures created by a man named Elmer Long. Sadly, Elmer passed away in 2019, but his family continues to keep his beloved ranch open to the public, free of charge (however, donations are appreciated!). 

Route 66 travelers positively adore Elmer’s wide range of handiwork, which is made using repurposed glass, metal, and other recyclable material. Most prevalent, of course, are his bottle trees that glisten beneath the California sun. 

Fork in the Road 

📍 Pasadena

Who Doesn’t Love a Good Pun?

S. St. John Avenue | Pasadena | www.atlasobscura.com

At Pasadena Avenue and Bellefontaine Street, you’ll find a fork in the road—literally. This otherwise ordinary intersection in Pasadena achieved national attention when two local business owners Bob Stane and Ken Marshall erected an 18-foot tall fork to mark the split in the road. Because Stane and Marshall executed their next-level pun without the city’s consent, the now-famous fork was taken down temporarily, only to be rebuilt after widespread outrage. 

Only about 15 minutes from LA, Fork in the Road is one last stop to make before finally arriving at the City of Angels. Even if you just jump out of the car for a minute to snap a quick photo, this punny point of interest is worth driving by—because how often do you get to see a dad joke come to life in such a big way?

Eight States, 2,000+ Miles, and Countless Memories 

It might be a long road to LA, but that doesn’t mean it has to be a boring one. Whether you’re a planner or someone who’s more spontaneous, road trips are one of the most fun—and eventful—ways to travel, especially if you find the right people to go with. While it’s certainly true that LA has just about everything that you could ask for in a destination, that doesn’t mean that you can’t find other places to fall in love with on your way there. So, pack your bags… It’s time for an adventure!


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Albion Skeldon

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