The cross-country road trip from Chicago to Los Angeles is a daunting yet rewarding driving vacation to attempt. There are two main routes road trippers can follow to get from Chicago to Southern California. The first is the quickest way to LA, passing through places such as Omaha, Denver and Salt Lake City, while the second route follows the iconic Route 66 through Missouri, Kansas, Oklahoma, Texas, New Mexico and Arizona before ending up in LA.
There’s no right or wrong way of road-tripping to LA from the Midwest, however, few road journeys can rival the mysterious towns, roadside attractions and stunning landscapes that the historic Route 66 offers. From Chicago and Springfield to Flagstaff and the Death Valley National Park, the most iconic way of travelling from Chicago to Los Angeles or Los Angeles to Chicago follows the remnants of the famous Route 66 through America’s Southwest.
Chicago To Los Angeles
20 Places To Explore On A Chicago To Los Angeles Road Trip
1- Route 66 Starting Point
The starting point of your epic road trip from Chicago to LA should, without a doubt, be the starting point of one of the most iconic stretches of road in the world, the famous Route 66.
Route 66 was first opened in 1926 and connected the Midwest to the West Coast via Illinois, Kansas, Missouri, Oklahoma, Texas, New Mexico, Arizona and California.
While the route was made redundant many decades ago, over 85% of the original Route 66 remains driveable, making it possible to drive from Chicago to LA almost exclusively on Route 66.
Route 66 starting point is at the corner of Jackson Boulevard and Michigan Avenue. If you’re spending the night in Chicago, you’ll find lots to do.
Recommended tour: Chicago Architectural River Cruise
Historic Springfield is the capital of the state of Illinois and the first stop along the Illinois section of Route 66.
Founded in 1821, the city is perhaps most famous for being the home of former US President Abraham Lincoln between 1837 and 1861, however, this sizeable city has plenty of other attractions and landmarks to enjoy.
One of the best landmarks in Springfield to see is, without a doubt, the Illinois State Capitol, where leaders like Lincoln and Barack Obama paved the way forward for Illinois and, eventually, the entire country.
Another great Springfield attraction is the Frank Lloyd Wright-designed Dana-Thomas House, built in 1904.
With so much to see and do, not to mention important history to uncover, Springfield is an absolute must on any Chicago to LA road trip.
Springfield is 201 miles (3 hours) from Chicago.
Recommended tour: Springfield City Scavenger Hunt
3- Shawnee National Forest
The massive 289 000-acre (116 954 ha) Shawnee National Forest is sandwiched neatly between the Ohio and Mississippi Rivers in the heart of southern Illinois.
Featuring an unblemished landscape highlighted by landmarks and features such as the Garden of the Gods, Jackson Falls and the Rim Rock National Recreation Trail, the forest is among the top outdoor attractions in the Midwest.
While not quite situated along the main route to LA, Shawnee National Forest is simply too beautiful and idyllic to miss out on during your Route 66 road trip to LA, perfect for an overnight camping adventure before heading west to St. Louis.
Shawnee National Forest is 216 miles (3.5 hours) from Springfield.
4- St. Louis
Nicknamed the Gateway to the West, the great city of St. Louis is famous for its rowdy sports fans, lively blues music scene and the world-famous Gateway Arch.
The city sits right on the Mississippi and Missouri River confluence, overlooks Illinois to the east, and is the second-largest city in Missouri.
Founded by French fur traders and named in honour of King Louis IX of France, St. Louis was placed firmly on the map when the Lewis and Clark expedition set off from the city in 1804.
Today, this modern and eclectic city boasts a rich craft beer industry, several interesting neighbourhoods and Forest Park, one of the greatest urban parks in America.
St Louis is 152 miles (2.5 hours) from Shawnee National Forest.
Recommended tour: St Louis Lemp Haunted Neighbourhood Walking Tour
5- Meramec Caverns
Situated underneath the Meramec Valley in eastern Missouri, the Meramec Caverns are a 4.6-mile-long (7.4 km) subterranean cave network located right along Route 66.
The caverns feature multiple Pre-Columbian Native American artefacts, a 6-foot tall (1.83 m) onyx table, a Mirror Room, and several other unique attractions.
Not only are the caverns among the most popular attractions along Route 66, but the caverns have also starred in several Hollywood films and TV shows, including Deep Impact, Lassie and Tom Sawyer.
The Meramec Caverns are 65 miles (about 1 hour) from St Louis.
6- The Ozarks
The Ozark Mountains, commonly referred to as the Ozarks, is a majestic physiographic region that spills into four states: Missouri, Arkansas, Kansas and Oklahoma.
Spanning over 47,000 square miles (122 000 km2), the Ozarks is a major ecological zone with idyllic mountainside towns and incredibly impressive geological features.
The Ozarks also feature the 165-mile (266 km) Ozark Highlands Trail, which connects the Buffalo National River with Lake Fort Smith State Park, ensuring you’ll never miss out on this amazing region’s raw natural beauty.
With plenty of campsites and hotels located all throughout the Ozarks, it’s easy to spend a couple of days here just exploring every nook and cranny of the Ozarks.
The Ozark Mountains is 206 miles (about 3.5 hours) from Meremec Caverns.
7- Oklahoma City
The largest city in the ‘Sooner State’, Oklahoma City is the state’s capital and is home to several attractions for visitors to soak up.
Nicknamed ‘OKC’, the city is home to the NBA’s Oklahoma City Thunder, the National Cowboy & Western Heritage Museum and the Oklahoma State Capitol.
Route 66 cuts right through Oklahoma City, making it an easy place to stop for a day or two.
This modern city treats visitors to world-class shopping and dining options, a bustling nightlife scene, and that unique Western charm to put you in the Frontier spirit during your once-in-a-lifetime road trip.
Oklahoma City is 305 miles (around 5 hours) from The Ozarks. You may want to break your journey in Tulsa, about a 3.5-hour drive from Ozark Mountains.
Recommended tour: Oklahoma City National Memorial Museum Tickets
8- Amarillo, Texas
Situated within the Texas Panhandle and near the halfway point of Route 66, Amarillo is a vibrant city with an incredibly diverse range of attractions and sights to behold.
The city was a major centre for cattle marketing in the region, however, Amarillo’s past includes all sorts of industries ranging from large-scale helium production to nuclear weapons.
With such a unique history, Amarillo stands out among the other cities along Route 66, boasting many attractions such as the Palo Duro Canyon State Park and the Cadillac Ranch.
Stopping by Amarillo is a real treat during any Chicago to LA road trip, thanks to the city’s great mix of old and new architecture, rich culture and collection of unusual roadside attractions.
Amarillo is 260 miles (under 4 hours) from Oklahoma City.
9- Santa Fe
Crossing the state border into New Mexico and approaching Santa Fe, road trippers are immediately struck by the area’s many Pueblo-style buildings and adobe landmarks.
Santa Fe is New Mexico’s capital and is home to an incredibly rich arts scene that’s rumoured to be among the best in the world.
Although first settled by the Spanish in the 15th century, Santa Fe has been inhabited for thousands of years by the Tewa and Navajo people, giving Santa Fe an incredibly vibrant culture that few cities in the world can rival.
From its famous Santa Fe Plaza and Palace of the Governors to its Georgia O’Keefe Museum and unique New Mexican cuisine, Santa Fe is a truly spectacular destination on the road from Chicago to LA to stop at that’s packed with unique experiences to enjoy.
Santa Fe is 285 miles (4.5 hours) from Amarillo.
Recommended tour: Santa Fe Revisited
10- Meteor Crater Natural Landmark
Right before arriving in Flagstaff, road trippers are struck with one of the world’s most unique and awe-inspiring sights, the Meteor Crater Natural Landmark.
Located roughly 37 miles (60 km) east of Downtown Flagstaff, the Meteor Crater is over 3,900 feet wide (1,200 m) and 560 feet deep (170 m), making it one of the largest impact craters in the world.
The meteorite that caused the massive impact struck approximately 50,000 years ago, quite recent in geological terms.
Despite large efforts made to turn the crater into a recognised public landmark, the crater is still privately owned by the Barringer Crater Company, which prides itself on preserving the crater for future generations to experience.
Even though the crater is located on private property, it remains open to the public and features a museum and visitor centre for travellers to learn all about this famous Arizona landmark.
Meteor Crater Natural Landmark is 352 miles (about 5 hours) from Santa Fe. Along the way, you could stop at Albuquerque.
Situated within the tall mountainous terrain of Northern Arizona, Flagstaff is a true year-round vacation destination boasting indoor and outdoor activities to partake in every season of the year.
During spring, Flagstaff comes alive with vivid colours as the world’s largest emerald green ponderosa pine forest blooms.
In winter and autumn, Flagstaff transforms into Arizona’s own Aspen, with skiing and snowboarding opportunities available around every bend.
Summertime brings clear skies and a mild climate to Flagstaff, making for perfect hiking or camping opportunities.
It doesn’t matter what time of the year you decide to pass through Flagstaff, you’ll find lots to do in and around this amazing Arizona destination.
Flagstaff is 43 miles (44 minutes) from Meteor Crater Natural Landmark.
Recommended tour: Flagstaff Haunted History Tour
12- Grand Canyon
The Grand Canyon is THE must-see landmark during any road trip from Chicago to LA.
Situated within the Grand Canyon National Park, this iconic landmark is famous around the world for its stunning gorges, colourful cliffs and enormous size, as well as its unblemished landscapes and rich biodiversity.
With many activities around or within the canyon, such as an ultra-marathon and the popular Grand Canyon Skywalk, the canyon is among the world’s greatest outdoor attractions.
Not only is the Grand Canyon free to enjoy and packed with activities for all ages, but its convenient location right along the main route to LA makes it an absolute no-brainer to put on your road trip list.
Grand Canyon National Park is 75 miles (1.5 hours) from Flagstaff.
Recommended tour: Grand Canyon Railway Adventure Package
13- Zion National Park
The stunning Zion National Park is located in Utah’s southwestern corner and is roughly 250 miles (402 km) north of the Grand Canyon National Park.
Best known for its steep canyons, natural arches and rich Native American history, Zion National Park’s incredibly unique landscapes can be derived from the park’s geographic location at the conjunction between the Colorado Plateau, Mojave Desert and Great Basin.
Zion blends some of the best landscapes in the world to create one truly terrific outdoor destination that must be seen to truly believe.
The park is immensely popular as a camping and glamping venue, so there’s no shortage of fantastic overnight options to choose from if you’re planning on setting up camp for a day or two before hitting the road again.
While not quite on the main route to LA from Chicago, Zion National Park is worth the short detour from Arizona to truly take in all the sights and activities on offer within and around Zion National Park.
Zion National Park is 332 miles (5.5 hours) from Grand Canyon National Park and well worth the detour!
Recommended tour: Award-Winning UTV Slot Canyon Tour
14- Las Vegas Strip
When road-tripping west towards LA, you simply have to stop at Las Vegas, and in Las Vegas, there’s no other place quite like the Strip.
The highlight of any trip to Sin City and the heart of all the city’s action, nightlife and famous sights, the Las Vegas Strip is a 2.5-mile-long (4 km) stretch of hotels and casinos that cuts right through the city’s downtown area from north to south.
The Las Vegas Strip is a section of Las Vegas Boulevard, featuring all the ritzy venues Las Vegas is so famous for around the world.
One of the best ways of experiencing the Strip is by foot, to take in attractions such as The Venetian, Caesar’s Palace and the Bellagio, including top dining and shopping options in Las Vegas at night.
With so many great places to see and iconic landmarks in Las Vegas to visit, it’s best to allocate a couple of days just to explore every inch of this remarkable stretch of road in one of the world’s major entertainment hubs.
Las Vegas is 164 miles (under 3 hours) from Zion National Park.
Recommended tour: Las Vegas Helicopter Night Flight with optional VIP transportation
15- Death Valley National Park
The infamous Death Valley National Park is a place of uttermost extremes on the California-Nevada border.
The park’s hot daytime temperatures and frigid night-time conditions make it one of the most physically challenging parks to visit in the United States.
It’s in the Death Valley National Park where the highest ambient air temperature on Earth was measured in 1916, clocking in at a sizzling 134 °F (56.7 °C) on the thermometer.
Not only is the park’s extreme heat a challenge to overcome, but it’s also the driest place in North America.
Yet, despite its inhospitable nature, the park is home to splendid natural features and is a fantastic spot to gaze at the stars away from city light pollution.
Death Valley National Park is 118 miles (2 hours) from Las Vegas and can easily be done as a day trip from Las Vegas if you want to base yourself in the city for longer.
Recommended tour: Death Valley Small Group Day Adventure from LV
16- Mojave National Preserve
One of the major natural and historic landmarks in California, the Mojave National Preserve tells the story of man’s connection to the desert that’s more than 10,000 years in the making.
From the arrival of the first Native Americans millennia ago, this preserve has captivated visitors with its awe-inspiring dunes and Joshua Trees.
Mojave National Preserve is the third-largest protected stretch of land under the National Park Service’s care and is conveniently situated roughly halfway between Las Vegas and Los Angeles.
The preserve is amazing to visit and has unique natural landmarks to discover, such as the Mojave Desert Mailbox, the Lava Tubes Trail and the Mojave Memorial Cross for guests to enjoy.
Mojave National Preserve is 274 miles (2.5 hours) from Death Valley National Park.
Recommended tour: Valley of Fire and California Mojave Desert tour
17- San Bernardino National Forest
The scenic San Bernardino National Forest incorporates diverse climates and biomes to create an outdoor wonderland.
The sprawling forest’s landscapes range from barren desert to the tallest alpine mountain range in SoCal.
With over 820,000 acres (331,842 ha) of unblemished nature to uncover and stunning natural features to take in, such as the San Jacinto Mountains and Bighorn Mountain, it’s easy to see why locals flock to these foothills every year.
San Bernardino National Forest is 156 miles (under 3 hours) from Mojave National Preserve.
18- Hollywood Sign
Stopping by the world-famous Hollywood Sign is a rite of passage for many first-time visitors looking for famous landmarks in Los Angeles.
Perched atop Mount Lee, the Hollywood sign is one of the city’s most photographed sites and serves as a monument to Tinseltown’s film industry that’s so ingrained into SoCal and Western pop culture.
Even though direct access to the sign is strictly prohibited, the nearby Griffith Observatory and Mount Lee summit are two of the best places to see the sign up close.
A truly amazing spectacle to clap your eyes on for the first time, the Hollywood sign is a popular highlight of the entire road trip.
The Hollywood Sign is 122 miles (2.5 hours) from San Bernardino National Forest.
Recommended tour: The Official Hollywood Sign Walking Tour in Los Angeles (free water and photos)
19- Rodeo Drive
A convergence of upscale shopping and entertainment in Beverly Hills, Rodeo Drive is synonymous with luxurious boutiques and Hollywood’s elite.
Spanning roughly 2 miles (3.2 km) from Sunset Boulevard in the north to Beverwil Drive in the south, Rodeo Drive first began receiving an influx of high-end shops right around the start of the 1960s.
Even though shopping is the major attraction along Rodeo Drive, you don’t have to splurge to have a great time visiting this iconic LA landmark, thanks to the district’s beautiful architecture and scenery which can easily be enjoyed on foot.
Regardless of whether you’re planning a last-minute shopping spree or just window shopping, Rodeo Drive is unlike any other venue in the world, making it the perfect stopping point to say goodbye to Hollywood and Beverly Hills.
Rodeo Drive is 10 miles (28 minutes) from the Hollywood sign.
Recommended tour: Hollywood Sightseeing and Celebrity Homes Tour by Open Air Bus
20- Santa Monica
The famous seaside city of Santa Monica lies just outside Downtown LA and is the best place to end what is perhaps the most iconic road trip in the world.
Featuring an illuminated pier, energetic rooftop bars and clubs overlooking the ocean, and some of LA’s best restaurants, Santa Monica is the place to be in SoCal.
Not only is this vibrant city the beating heart of LA’s surfing and skateboarding scene, but it’s also renowned for its amazing arts and shopping scenes.
From its sandy beaches to Santa Monica Pier, Santa Monica is a fun place to end (or start your journey if you’re driving from Los Angeles to Chicago).
Santa Monica is 8.4 miles (15 minutes) from Rodeo Drive.
Recommended tour: Small Group Electric Bike Tour of Santa Monica and Venice Beach