A road trip from Chicago to Los Angeles will see you drive the length of the historic Route 66 in its entirety. This legendary road will take you between two of the largest, most famous cities in America, past some of its most famous attractions.
Along the way, you'll travel through a whopping 7 states. Beginning in Illinois, you will pass through Missouri, Oklahoma, Texas, New Mexico, and Arizona, before arriving at your destination in California.
With so much to see and do along the way, you aren’t going to want to miss anything on this amazing journey. So, if you are planning to drive Route 66 on a road trip from Chicago to Los Angeles, I highly recommend reading on.
A Road Trip From Chicago To Los Angeles: How Far Is It & How Long Will It Take To Get There?
A road trip from Chicago to Los Angeles takes you along the length of the historic Route 66. This is definitely not a journey for the faint of heart, as you will be travelling over 2,000 miles, which will take upwards of 30 hours.
While the original Route 66 is no longer drivable in its entirety, you can still follow roughly the same route, using a collection of newer roads interspersed with parts of the historic route itself.
However, it is important to note that the roads you choose can dramatically affect the time the journey takes. That’s why I am going to provide two routes; a straightforward one, and one that follows as much of the original route as possible.
No matter which route you take, the start point for our journey is the Historic Route 66 Begin Sign, located opposite the Art Institute Of Chicago.
The Simple Route
Head south on South Michigan Avenue and turn right onto East Ida B. Wells Drive. Follow it onto the Chicago – Kansas City Expressway and immediately exit to go south on I-90.
Take exit 53 in the south of the city to join I-55, going southwest.
You’ll follow this for 300 miles to St Louis, Missouri, where you’ll take exit 40B W to go west on I-44. You’ll remain on this road until you reach Oklahoma City, some 500 miles away.
Upon reaching the city, take exit 120A to join the I-40. You’ll then follow this west for most of the 1,200 miles to where it terminates in Barstow, California.
With the bulk of the journey behind us, begin heading south on I-15 to exit 115A, where you’ll head west on Route 210. Pick up I-605 where it begins and follow it south to exit 22.
From here you’ll join the I-10 going west and follow it the final 30 miles, to our destination at the Route 66 End Of The Trail sign on Santa Monica Pier.
Drive Route 66
Begin by heading west on East Adams Street and continue following it to Heritage Green Park, where you turn left onto South Desplaines Street.
Take a right onto West Van Buren Street, then the first right onto South Halsted Street, before turning left onto West Adams Street.
Turn left onto West Ogden Avenue and follow it for 8.5 miles, where you’ll join Illinois Route 43 going south. Just a short while later, exit onto Joliet Road and continue following it when it becomes 55th Street. Turn left onto East Avenue, then right to re-join Joliet Road.
Large sections of the road will now simply be labelled Historic US-66, which you’ll follow until just before the Dupage River. As the road becomes W Main Street, turn left to stay on Historic Route 66.
Exit when you reach Gardner and turn left onto County Road 7000 S, before immediately turning right and then right again to remain on Historic US-66. Eventually you will reach a sign in the town of Towanda where Historic US-66 and Old US Route 66 split.
Turn right to stay on Historic US-66 then left on the freeway to follow it south. Take the first exit, just before the Bloomington Water Tower, then turn left to stay on Historic U.S. 66.
Turn right just before the S Veterans Pkwy freeway onramp, then left immediately after you pass over the top of it.
When you reach the town of McLean you will briefly turn right onto Dixie Rd, before almost immediately turning left back onto Route 66. When you reach the Lincoln Pkwy onramp take a left to stay on Route 66, then veer left again when you reach the crossroads.
Take a right onto Illinois Route 123 in Williamsville then join I-55 going south. Follow this until you reach St. Louis, where you will use exit 40A. Turn right then right again to get back onto Route 66.
Turn right onto Chouteau Avenue then left onto Tucker Boulevard. At the intersection, bear right onto Chippewa Street. After 12.5 miles, you’ll reach a flyover, where you head north on US-61 until you reach Missouri Route 100.
Follow this until it passes over the I-44, just before the town of Villa Ridge. When it veers right, continue straight to remain on Route 66. The road will cross back and forth across the I-44, running mostly parallel until you eventually merge with US-63 in the town of Rolla.
Turn right onto Kingshighway and then merge with I-44. Once you reach the town of Vinita in Oklahoma, turn right onto US-60. From here, Route 66 will largely be signposted, using parts of I-35 and I-44 along the way.
You will eventually merge with the I-40 at exit 108. From here, the route will be almost identical to above, following the I-40 most of the way. The only exceptions are a few detours through some of the most historic Route 66 towns. These are:
· Exit 101 to 84
· Exit 80 to 71
· Exit 41 to 32, through Elk City
· Exit 25 to 176, through Sayre, Hext, Erick, and Texola
· Exit 164 To 161, through Shamrock
· Exit 157 to 152
· Exit 114 to 110 through Groom
· Exit 98 to 89
· Exit 85 to 62A, through Amarillo.
· Exit 37 to 35, through Vega
· Exit 23 to 22, through Adrian
· Exit 0 to 329, through Glenrio, San Jon, and Tucumcari
· Exit 277 to 273, through Santa Rosa
· Exit 197 to 149, through Moriarty, Edgewood, Tijeras, Carnuel, and Albuquerque
· Exit 114 to 47, through Laguna, San Fidel, Grants, Milan, and Prewitt
· Exit 36 to 15, through Gallup
· Exit 204 to 191, through Flagstaff
· Exit 165 to 151, through Williams
· Exit 139 to 1, through more than a dozen towns, including Seligman and Kingman
Best Time For A Road Trip From Chicago To Los Angeles
While there is nothing stopping you from driving Route 66 at any time, the best time for a road trip from Chicago to Los Angeles is between early May and late September.
This is a timeframe where the weather is pleasant the whole way along the route, and you can ensure that the vast majority of attractions will be open.
August is a particularly good choice, as there are a number of events taking place along Route 66 that can add even more value to your trip.
Top Attractions On A Road Trip From Chicago To Los Angeles
The whole point of a road trip from Chicago to Los Angeles along Route 66 is to take the opportunity to stop and see the sights along the way.
On a journey like this there is simply far too much along the route to list everything, especially as many of the attractions are niche options that will only appeal to a certain audience.
With that in mind, I have compiled the following list of must-see attractions. These are the destinations that have the most to offer and are sure to entertain the vast majority of travellers.
Joliet, Illinois
The 3rd largest city in Illinois and the first major location along Route 66, it has plenty of attractions related to the history of the historic route.
The Route 66 Visitors Centre is a great place to learn about the journey you are embarking on, while the Route 66 Raceway and Chicagoland Speedway both embrace the auto industry that put the city on the map.
Other attractions include the Joliet Area Historical Museum, the historical Joliet Correctional Center, a pair of casinos, and the Rialto Square Theatre, a favourite destination of infamous Illinois gangster Al Capone.
Springfield, Illinois
The largest city in Illinois outside the Chicago Metropolitan Area, Springfield is best known for being the residence of former U.S. President Abraham Lincoln between 1837 and 1861. He lived in the city working as a lawyer right up until he was elected to the White House.
The Abraham Lincoln Presidential Library And Museum, Lincoln Home National Historic Site, Lincoln-Herndon Law Offices State Historic Site, and the Lincoln Tomb are all located in the city.
This makes it a great stop for anyone interested in one of the nation’s most famous politicians.
Stanton, Missouri
A small town in eastern Missouri, Stanton is surrounded by attractions like the Meramec Caverns, Meramec River, Riverside Wildlife Center, and Wild Animal Adventure. This makes it a great place to get out and stretch your legs for anyone interested in nature or wildlife.
In the town itself, you also have a popular attraction that is the Jesse James Wax Museum, which teaches about the life of the region’s infamous outlaw through wax works and videos.
Springfield, Missouri
Known as the Birthplace Of Route 66, there are plenty of historic locations and establishments to revel in during your journey.
For those travelling in August, the crown jewel of the city is the Route 66 Festival, which is held along the route itself, as well as in Central Square.
Parades featuring vintage cars and performers travel along Route 66, while vendors in the square sell food and drink, as well as souvenirs and literature relating to the road, all while live performances take place around the park.
Joplin, Missouri
Joplin has an automotive history relating to something other than Route 66, as it was one of the hideouts of the notorious Bonnie & Clyde during their rampage. After robbing numerous businesses, a police shootout saw them flee, leaving behind many of their most personal possessions.
The Joplin Museum Complex features exhibits including some of the couple’s personal belongings, as well as the original copies of some of their most iconic photos.
As for its history with Route 66, you also have the Route 66 Mural Park. Here you will find a selection of beautiful murals dedicated to the legendary road.
Tulsa, Oklahoma
The 2nd largest city in Oklahoma, Tulsa is settled on lands considered Indian Territory. With numerous museums, as well as cultural and historical archives, it is one of the best places to come to learn more about the history of this part of the country.
The city itself features a fabulous collection of parks, works of art, and performance venues, as well as the sort of nightlife and amenities you would associate with a larger city.
You will also find the Golden Driller Statue, as well as the Meadow Gold sign, one of the most iconic landmarks along Route 66.
Oklahoma Route 66 Museum
Located in the small town of Clinton, the Oklahoma Route 66 Museum contains signs, photos, memorabilia, and a replica diner, dedicated to the history, myths, and music of Route 66.
National Route 66 And Transportation Museum
The National Route 66 And Transportation Museum is a large complex found in Elk City, Oklahoma. More than just a museum dedicated to Route 66, it also features a recreation of a town as it would have looked from when the area was first settled up to the completion of the road.
With locations like an undertaker, opera house, school, post office, diner, law office, general store, furniture store, black smith, and train station, it is a fabulous place to take a journey back into the past.
Musical Highway, America The Beautiful
A unique attraction made from rumble strips along the highway. Make sure to maintain a speed between 40 to 45 miles per hour and the vibrations of the car will play America The Beautiful as you drive.
El Malpais National Monument
A rugged volcanic landscape, it is a popular hiking and caving destination, which offers scenery unlike anything else you are likely to find in the region.
Gallup, New Mexico
Known as the “Native American Capital Of The World”, Gallup gained fame in the 1930’s as a getaway for stars trying to escape the paparazzi in Los Angeles or Las Vegas.
Famous names like John Wayne, Catherine Hepburn, the Rat Pack, and even former U.S. President Ronald Regan took refuge here. With its historic hotels, markets, and murals, it is a fabulous destination to soak up history and culture across the board.
Petrified Forest National Park
Covering over 220,000 acres, Petrified Forest National Park is the only National Park located directly along Route 66. It is a wonderful attraction filled with archaeological sites and fossils, as well as colourful painted deserts and petrified wood.
The park is also home to numerous species of animals, such as coyote, deer, pronghorn, and more than 200 species of birds, including roadrunners.
Winslow, Arizona
Known for its murals, Winslow is a historic town that has been restored with bars and stores designed to educate and entertain those driving, or interested in, Route 66.
Meteor Crater Natural Landmark
Meteor Crater Natural Landmark is a massive meteor impact site, giving you the opportunity to see the size of a crater first-hand.
A theatre and interpretive centre help to teach you about the crater and the effect of meteors, while a gift shop and concessions will take care of your dining and keepsake needs.
Grand Canyon National Park
One of the most visited natural attractions on Earth, Grand Canyon National Park is home to one of its largest canyons. Carved by the Colorado River over millions of years, it runs for 277 miles, with widths between 4 and 18 miles and a depth of over a mile in places.
Continuously home to Native American’s, it is considered a holy place for numerous tribes.
With some of the most breathtaking views you will ever experience, as well as features like historic dwellings, waterfalls, historic trails, and an abundance of wildlife, it is a can’t miss destination for anyone who has never visited before.
Williams, Arizona
One of the most famous towns along Route 66, Williams is filled with Americana style shops and restaurants, themed and dating back to the early 1900’s.
Pete’s Route 66 Gas Station Museum contains a museum and a selection of vintage vehicles, while the Route 66 Zipline will give thrill-seekers the chance to get their blood pumping.
You also have Bearizona Wildlife Park, where you have the chance to see bears, bison, mountain goats, and birds of prey, up close and personal.
Seligman, Arizona
The Seligman Commercial Historic District was designated a historic highway by Arizona in 1978 and added to the National Register Of Historic Places in 2005. Another town claiming to be the birthplace of Route 66, businesses and buildings here date back as early as 1903.
Among them are a gas station, general store, post office, pool hall, and theatre. With some still in operation, others preserved as museums, and themed bars, shops, and restaurants dotted throughout, it is a wonderful little stop offering both history and entertainment.
Kingman, Arizona
The last of the trio of historic towns in this part of Arizona, Kingman features the Mohave Museum Of History And Arts, the Kingman Railroad Museum, the Arizona Route 66 Museum, and a locomotive park with a 1920’s steam engine.
Havasu National Wildlife Refuge
Havasu National Wildlife Refuge is a protected area that is an important wetland habitat for breeding, migrating, and nesting birds.
Nature lovers and bird watchers can take the opportunity to spot some rare and interesting species, such as peregrine falcons and roadrunners.
Mojave National Preserve
The Mojave National Preserve is a 1.6-million-acre dessert wilderness, popular for hiking, horse riding, and four-wheel driving. It features historical markers and the Kelso Ghost Town, which has a historic rail depot you can explore.
Calico Ghost Town
Located in the hills northeast of Los Angeles, Calico is an abandoned silver mining town that has been maintained to look how it historically would have. It is easily visible from the highway, due to its name being marked out in white rocks on the side of the hill.
Among the top attractions are a train ride down into the mine, faux stores showing how traditional goods were made, and a saloon serving old-fashioned sarsaparilla.
Barstow, California
A famous railroad depot, Barstow is home to the Barstow Route 66 Mother Road Museum. The town is a great place to explore the history of the railroad, while the museum features artwork, historic vehicles, photographs, and petrolania dedicated to Route 66.
Best Places To Stop On A Road Trip From Chicago To Los Angeles
There’s no two ways about it, a road trip from Chicago to Los Angeles is a trip of such magnitude that you are going to need to make a number of overnight stops along the way.
While there are countless options available, I am going to suggest one from each state you travel through, so you can fully experience the range of cultures there is to encounter on your journey.
St. Louis, Missouri
St. Louis is the 2nd most populous city in the state of Missouri, lying on the banks of the Mississippi River.
Known historically as the “Gateway To The West”, due to being the last major city before the frontier in the old west, its most famous attraction is the Gateway Arch. Standing 630 feet high, the monument is a stunning piece of architecture, located right beside the river.
Designated a National Park, it is the tallest man-made monument in the world, paying homage to the city’s importance during the westward expansion of the United States during the 1800’s.
St. Louis is equally as historic when it comes to the music industry as well, specifically the blues genre. One of the most important musical cities in the world, you have the opportunity to see iconic locations like Gaslight Square, where the genre exploded in the 50’s and 60’s.
Countless bars litter the city, giving you the chance to enjoy an evening out, listening to the sort of sounds that made it famous.
You even have iconic venues such as Blueberry Hill to visit, as well as the chance to see the second oldest symphony orchestra in America, the St. Louis Symphony Orchestra.
For those not as interested in history or music, there are numerous other attractions to enjoy in St. Louis, such as museums, zoos, and botanical gardens.
Best Hotel To Stay At In St. Louis – Hyatt Regency St. Louis At The Arch
Located immediately opposite Gateway Arch National Park, the Hyatt Regency St. Louis At The Arch is a stunning, 4-star hotel. This wonderful location gives you the ability to wake up each morning to views of the city’s most famous attraction.
The rooms are all modern and stylishly decorated, providing you a high-level of relaxation throughout your stay. With a 24-hour gym and a fabulous restaurant on site, it is the perfect combination of comfort and convenience.
Oklahoma City, Oklahoma
The capital and largest city in the state of Oklahoma, OKC was founded during the Oklahoma Land Rush of 1889. A city that thrives on business and industry, it is also a destination that is known for its abundance of cultural and historic establishments.
Museums such as the National Cowboy And Western Heritage Museum, the Oklahoma City Museum Of Art, the Oklahoma Science Museum, and the Oklahoma History Center are designed to help visitors learn and understand more about the history of the city.
Meanwhile, its extensive collection of parks and theatres give you places to relax and unwind, while soaking in the culture of the region.
Combined with a thriving downtown area full of bars and restaurants, Oklahoma City is a perfect place to stop for a well-rounded break from the road.
Best Hotel To Stay At In Oklahoma City – The Skirvin Hilton Oklahoma City
Located at the heart of Downtown Oklahoma City, The Skirvin Hilton Oklahoma City is a stunning hotel, located in a beautiful, historic building. From the exteriors to the lobby and corridors, this is a location that will make you feel like royalty from a bygone era.
You can make the most of this in places like the hotel’s Park Avenue Grill Restaurant, or its Red Piano Bar, where you can enjoy cocktails and live music. There is even a swimming pool for guests who want to stay a little more active.
In contrast, the rooms are all modern, yet maintain a similar level of style. Sleek, comfortable furnishings are complimented by more high-tech amenities like flat screen TVs, Wi-Fi, and serenity beds.
With the Bricktown Entertainment District, the State Capitol Building, and the Oklahoma City National Bombing Memorial within minutes of the front doors, you will have plenty to keep you busy both in and around this amazing property.
Amarillo, Texas
Amarillo is a beautiful city that is the largest and most populous in northwest Texas. Being from the more rural part of the state, it features a lot more of the stereotypes people associate with Texas than you will find in the bigger cities.
All the 10-gallon hats, great steaks, cowboy boots, and ranchers you could ever hope to see turn Amarillo into the ideal place for those wanting to experience the “real” side of Texas.
As a result, it has also been used to film numerous westerns over the years, so movie buffs may be able to spot some familiar locations. While the city itself has lots to offer, there is plenty going on in the surrounding area as well.
The Caprock Canyons State Park And Trailway, houses the official Texan bison herd, where you can enjoy its iconic wildlife.
The Alibates Flint Quarry National Monument was where ancient native settlers constructed tools and weapons, allowing you a glimpse into the region’s history.
There is even Palo Duro Canyon State Park, the second largest canyon system in the United States, for those who love nothing more than taking in the beauty of the country.
Best Hotel To Stay At In Amarillo – Route 66 Inn
Located just outside the Route 66 historic district, on the legendary road itself, the Route 66 Inn is the perfect place to immerse yourself in the spirit of the trip.
A modest accommodation, it is the surroundings, such as the nearby Amarillo Museum Of Art, as well as the style that sell this property.
That said, home comforts and appliances like a microwave, refrigerator, cable TV, Wi-Fi, and free parking help make it a welcome pit stop on an incredible journey.
Albuquerque, New Mexico
The largest, most populous city in New Mexico, Albuquerque is a beautiful place, filled with bars and restaurants boasting a vibrant Mexican culture.
The must-see locations in the city include Historic sites like the San Felipe De Neri Church and the stunning views from the Sandia Peak tramway, the longest aerial tram in the Americas, in the nearby Cibola National Forest.
Combined with racetracks and casinos, it is a city with a wide range of options to keep everyone happy during their visit. Depending on what time of year you choose to visit, Albuquerque also hosts numerous events and festivals throughout the year.
Occasions like the International Balloon Fiesta, Gathering Of Nations, and the New Mexico State Fair give you plenty of chances to soak up the culture of the city.
In the surrounding area, the historic Bandelier National Monument, the beautiful Cibola National Forest, and the incredible Sevilleta National Wildlife Refuge provide a range of attractions to amaze people of all tastes and interests.
Best Hotel To Stay At In Albuquerque – Hotel Chaco
Set in the Old Town section of Albuquerque, Hotel Chaco is situated in a historic building, which immerses you in your iconic surroundings. With attractions aplenty within walking distance of the property, it is truly the height of culture and convenience.
Amenities like a restaurant, bar, fitness centre, and outdoor swimming pool provide all the convenience you would expect from a 4-star hotel.
Meanwhile, the rooms are all spacious and beautifully furnished, ensuring a comfortable visit, no matter how long you choose to stay.
Flagstaff, Arizona
Flagstaff is an often-overlooked city, yet it is a place that may have the best collection of natural wonders you will find anywhere in America. In fact, one of its nicknames is "the city of seven wonders”, due to just how much there is to do and see in the area.
Among them are the towering Humphrey’s Peak, the stunning Slide Rock State Park and Sunset Crater Volcano National Monument, the historic Wupatki National Monument and Walnut Canyon National Monument, and the crystal waters of Mormon Lake.
The 7th wonder is one that has earned the city another nickname, “the city in the pines”, that being Coconino National Forest. At nearly 2 million acres, it is the largest Ponderosa pine forest in North America.
Throughout it you will find miles of hiking trails, weaving through incredible scenery that is alive with wildlife. On top of all this, you even have the Grand Canyon located less than an hour to the north.
This all makes Flagstaff an incredible choice for anyone who loves going on an adventure.
Best Hotel To Stay At In Flagstaff – Little America Hotel Flagstaff
The Little America Hotel Flagstaff is the ideal place to stay during your trip to Flagstaff. A rustic hotel, designed like a traditional log cabin and lodge, located right on the edge of Coconino National Forest, it perfectly represents the natural beauty of this incredible location.
Despite its more traditional design, this isn’t by any means a “simple” property though. Beautiful furnishings and modern-day luxuries like Wi-Fi and a swimming pool provide all the exclusivity you would find at any top resort.
This all combines to make the Little America Hotel the perfect mix of style, quality, and location, to perfectly compliment your trip and allow you to make the most of this beautiful and historic city.
Conclusion
A road trip from Chicago to Los Angeles along Route 66 is a fabulous endeavour. You travel between two amazing cities, along a route that is filled with history and stunning locations.
While the shorter route will be appealing to some, I’d highly recommend taking the extra time to use the more scenic route if you can.
This article should have given you everything you need to plan your perfect trip along Route 66, making stops at all the iconic locations you will have heard of. So, all that’s left is to start making plans and getting things booked, so you can hit the road as soon as possible.
