Whether you want to enjoy spectacular views, revel in natural attractions or experience urban thrills, a Chicago to California road trip is an excellent fit.
This Chicago to California road trip offers a wide range of attractions, scenic views, and experiences, fitting all itinerary needs. You will pass through bustling metropolises and long stretches of remote areas along the route. The road trip crosses eight states and three time zones, featuring various stopovers along the way.
Stops
1. Chicago
2. St. Louis, MO
3. Oklahoma City, OK
4. Amarillo, TX
5. Santa Fe, NM
6. Santa Monica, CA
Info at a glance
- A 2-week trip
- Type of route: Family
- 6 stops along the route
- 2,056 miles of driving
Highlights
- Explore the diverse arts scene at the various art exhibits in Chicago.
- Visit the Garden Arch architectural masterpiece and enjoy spectacular views of St. Louis.
- Enjoy a nature tour at Oklahoma city’s Myriad Gardens.
- Relive Texas’ history at Amarillo museums.
- Immerse yourself in music culture at the Santa Fe Opera.
Getting to the start
The road trip starts in Chicago, Illinois. If you are coming from a different part of the country, you can opt for a flight to Chicago O’Hare International Airport. Alternatively, you can drive in via I-94 from the north or south or I-55 from the west. Also, you can consider a train trip via Amtrak, which has frequent departures to Chicago from various locations in the country.
When to Visit
The best time to embark on a Chicago to California road trip is between late spring and early summer. Therefore, consider scheduling your road trip between April and June if you want to enjoy fun-filled outdoor activities. Also, pack for various weather conditions, with blankets and fleece jackets for chilly nights, to sunscreen, shorts and T-shirts for warmer afternoons.
Driving tips
Speed limits along the road trip route vary as you will be driving on both major highways and other roads throughout the route. However, if you wish to make up time during the trip, you can undoubtedly utilize the Interstate. There are no tolls along the route.
What to know about the route
This 1,250-mile road trip from Chicago to California would take 40 hours if you were to have a direct trip. However, the direct journey will be tiring and short of attractions and thrilling travel experiences. The entire route we have chosen is along the historic Route 66, but on parts that are otherwise not passable, you will use I-40. You will drive southwest along Route 66 to St. Louis, then proceed to Oklahoma City across the state. After that, you will drive west to Amarillo in Texas before heading to Santa Fe along Route 66 with stretches of I-40. When your time in Santa Fe is done, proceed to the final stop, Santa Monica. An SUV is ideal for this road trip, as it has plenty of cargo and passenger space.
Chicago
Chicago offers everything you might desire in an international city. From unique architecture to excellent cuisine, great outdoor destinations and attractions. The city boasts significant contributions to US history, art, music, culture, sports and innovation. Also, Chicago’s location on Lake Michigan and diverse population give you a true city experience.
Points of interest
Regardless of your art taste, you will always find something intriguing in Chicago’s art scene. Spend a few hours at the Art Institute of Chicago for world-class art exhibitions from renowned artists. Also, if you are a history buff, then Chicago has you covered. Visit the Field Museum to explore natural history or learn more about the city at Chicago History Museum.
Where to eat, drink and sleep
Chicago features a diverse culinary scene with a wide range of dining options, serving cuisines from all over the world. To experience the famous deep-dish pizza, head to Bartoli’s Pizzeria, a family-run restaurant. You can also savor flavors from various regions in the world at foodie neighborhoods in the city, including Chinatown, Little Italy and Greektown.
Sixt Insider Tip
Sports are a big deal in Chicago, and the city is home to major professional teams, including the Cubs, Bulls and Bears. Catching a home game during your visit is a great way to experience Chicago’s electric sports atmosphere.
From Chicago to St. Louis (297 miles)
From the Windy City, proceed southwest along Route 66 (I-55) to St. Louis. This scenic route highlights the Midwestern charm, featuring cities and small towns along the way. You can stop in Springfield, Illinois, to grab a bite to eat or refill your gas tank as you enjoy the Greek architecture in the city.
St. Louis, MO
With a blend of Midwestern charm and urban bustle, St. Louis is worth a stopover. The city features a broad array of neighborhoods, from diverse culinary hotspots to historic architecture and a range of attractions. Boasting a list of dynamic museums, lovely gardens and parks, sporting events, and fun-filled outdoor activities, St. Louis has something for everybody.
Points of interest
The Gateway Arch will offer you breathtaking views of the River City from its observation platform about 625 feet in the air. Die-hard baseball fans should not miss a visit to Busch Stadium, home of the award-winning St. Louis Cardinals, to enjoy the sports spirit in the city. The Delmar Loop, one of the best streets in the city, will provide you with entertainment options, unique boutiques and art galleries.
Where to eat, drink and sleep
From St. Louis-style barbeque to premium pub cuisine and fresh Bosnian and Italian specials, there is plenty to savor in the city. Walk into Bogart’s Smokehouse for tantalizing St. Louis-style ribs or Charlie Gitto’s for Italian fare. If you want to spend a night in St. Louis, consider checking in at Four Seasons Hotel.
Sixt Insider Tip
A stop in St. Louis is not complete without visiting the spectacular Forest Park, the largest city park in the country. This unique park is also home to the St. Louis Zoo and a few museums, offering you a lot to explore.
From St. Louis to Oklahoma City (499 miles)
Proceed on the historic Route 66 (I-44 W) to the next stop, Oklahoma City. As you head west, states get more expansive, and the landscapes seem to stretch forever. However, you can make stopovers along the route, like in Tulsa, Oklahoma, for refreshments and break the monotony.
Oklahoma City, OK
Although Oklahoma City is not often included in most travelers’ itineraries, it is worth a stop. The city has a lot to offer, including hidden trails and other gems. From educational attractions to a growing art scene, an exciting cowboy vibe, and fantastic food, a stopover in the city is sure to be worth it.
Points of interest
Paseo Arts District is a haven for art enthusiasts, featuring various galleries to explore local artwork. Stockyards City, a few minutes away, will offer you an authentic taste of the Old West. Nature lovers will enjoy touring the Myriad Gardens, a lovely park with a range of plant species and scenic views.
Where to eat, drink and sleep
Years of evolution have transformed Oklahoma City’s culinary scene into a unique fabric in which local flavors merge with international cultures. Treat your taste buds with authentic Lebanese cuisine at Nunu’s Mediterranean Café or grab a cocktail at a bar in downtown Oklahoma City. For overnight stays, book a room at Sheraton Oklahoma City Downtown Hotel.
Sixt Insider Tip
Oklahoma City is home to some of the most spectacular sunsets in the country. Due to its flat topography, you can catch a glimpse of the stunning sunsets regardless of where you are in the city. To experience the best sunset views, visit one of the city’s many lakes in the evening where you can see amazing reflections of the sun.
From Oklahoma City to Amarillo (260 miles)
After you are done in Oklahoma City, proceed further along Route 66 (I-40 W) into Texas. This journey across states features scenic desert views and a few towns along the way. You can briefly stop in Clinton to check out the iconic Oklahoma Route 66 Museum. Continue until you reach Amarillo in Texas.
Amarillo, TX
This quaint, modest city in the High Plains of West Texas has some surprises for travelers and some of the finest attractions and outdoor activities. Amarillo boasts a distinctive fusion of two US eras, with thriving Western ranches and a bustling urban economy, offering an ideal balance of classic and contemporary Texas heritage.
Points of interest
To experience West Texas history and culture, explore the various museums in Amarillo, including the Panhandle Plains Historical Museum and Quarter Horse Museum. If you seek fun and creativity, head to the unique Cadillac Ranch and immerse yourself in graffiti. Amarillo Zoo offers you the opportunity to catch a glimpse of some exotic animals.
Where to eat, drink and sleep
For excellent steak, try out Tyler’s, home to some of the best meat platters in the city. Also, you can check out the Golden Light Café, the oldest dining option in the city, for classic American specials. Also, whether you prefer craft beer, wine or cocktails, you will find something fitting your needs at Six Car Pub & Brewery.
Sixt Insider Tip
Get out of the car and explore the Amarillo Botanical Gardens. The gardens, which cover four acres, include indigenous flora outside, a fragrance garden, and exotic plants within the conservatory, ideal for a day in nature.
From Amarillo to Santa Fe (280 miles)
From Amarillo, head west on Route 66 (I-40 W) and enter New Mexico, where you’ll find the next stop. You’ll pass by the iconic Blue Swallow Motel in Tucumcari and will then take a slight detour north on Highway 285 to Santa Fe. You can enjoy scenic views of New Mexican farm life scattered along the route.
Santa Fe, NM
Santa Fe, the nation’s oldest state capital, is among the country’s most historic and intriguing cities. While history is evident in Santa Fe, the city also boasts a vibrant modern and elegant side. Santa Fe is exciting while also being restful and fun, and you’ll find conventional attractions with contemporary twists.
Points of interest
A visit to the Santa Fe Opera offers a unique music experience. This theater features superb music performances and fantastic architecture to relish during the stop. Also, art lovers will be blown away by the Canyon Road Art District, featuring various galleries that exhibit 20th century and contemporary artworks.
Where to eat, drink and sleep
Santa Fe’s cuisine, which ranges from authentic Native American and Mexican fare to locally produced specials like green chilis, is a foodie heaven. Check out Second Street Brewery for amazing beer and live music performances. You can also walk into India House to savor South Indian Cuisine.
Sixt Insider Tip
Loretto Chapel is a must-see during the stay at Santa Fe, as it is a spot where mystery, history and architecture come together. It’s the ideal place to cool down after a thrilling tour of the city while learning about the anonymous man who created the physics-defying spiral stairs.
From Santa Fe to Santa Monica (720 miles)
On the way to the final stop, Santa Monica, you will be driving across Arizona into California. You will take I-25 S to meet back up with I-40 W, which you will continue on, along with some highways, until you reach Barstow, California, where you’ll take I-15 S This stretch is the longest for the road trip; therefore, ensure you start your journey early. There are several small towns and some cities along the way, and you can have a brief stop in Sedona, Arizona, to stretch your legs and grab a bite.
Santa Monica, CA
Santa Monica, California, marks the culmination of the historic Route 66, with Baywatch-style beaches and an amusement park awaiting you at the end of a long journey. The city is an ideal location for travelers owing to its accessibility to the broader Los Angeles area. This laid-back metropolis is all about unwinding and year-round warm weather.
Points of interest
Enjoy lazy afternoons at Santa Monica’s beaches, which cover a 3.5-mile stretch of the spectacular Californian coastline. With such stunning beaches, the city’s sunsets are amazing and worth waiting at the beach for the best views. Shopping fans will adore the city’s 3rd St., where you’ll find premium shopping outlets and boutiques.
Where to eat, drink and sleep
Santa Monica boasts a range of dining options, from chic establishments to informal cafés. Consider checking out Lanea for Mexican fare or Fritto Misto for Italian specials. For an overnight in the city, book a room at the Ambrose Hotel.
Sixt Insider Tip
Santa Monica’s wealth of trails and pleasant weather make it ideal for cycling. Also, downtown Santa Monica features the Marvin Braude Beach Trail, as well as bike-friendly boulevards.
