Route 66 Holidays: How to Plan an Epic Chicago-to-California Road Trip

Nothing quite conjures up the carefree American adventure like the iconic Route 66 road trip. At one end lies Chicago, a city of vibrant contrasts and character, and at the other, Santa Monica in California, with its sun-kissed beaches and laid-back vibes. 

‘The Mother Road’ sweeps through the heart of the country, traversing an impressive eight states in total. By cruising Route 66, you will take in perfectly preserved pockets of classic Americana, from old-school gas stations, neon-lit signs, historical sites, charming towns, dusty scenic landscapes, and glitzy cities.  

When it comes to planning such a vast itinerary, you might be wondering where to start. But that’s where we come in! As USA travel specialists, we can give you the road map to your travel dreams.   

Whether you decide to do the Full or Half Route 66 tour, travel east to west, or vice versa, you’re in for an epic adventure… 

Suggested Itineraries 

The Classic Route 66 journey includes stops in Chicago (Illinois), St Louis and Springfield (Missouri), Oklahoma City (Oklahoma), Amarillo (Texas), Albuquerque (New Mexico), Flagstaff (Arizona), the popular side-trip in Las Vegas (Nevada), and Barstow and Santa Monica/Los Angeles (California). Set over 22 incredible days, you’ll have the opportunity to experience some of the best tourist spots in the US for an all-encompassing adventure of fun, nature, and rich history. 

If time isn’t on your side, the excellent Half Route 66 option covers plenty of ground over a shorter 17-day period between Chicago and Albuquerque, with additional stops to savour the vibrant cultural flavours of Tulsa in Oklahoma and the small-town nostalgic charm of Tucumcari in New Mexico. 

Highlights 

With so much to pack in, you could drive Route 66 multiple times and stop at different places every time. We’ve picked some of our favourite, must-visit locations en route to highlight and give you plenty of inspiration for your next big road trip: 

Chicago, Illinois

Start in the Windy City, with three nights exploring renowned landmarks like Willis Tower and its lofty Skydeck on the 103rd floor, the tranquillity of the Chicago Riverwalk, and ‘The Bean’ sculpture located at Millennium Park in the heart of downtown. No visit to Chicago should miss dining out on its famous deep-dish pizza - look out for a Lou Malnati’s, a firm favourite chain with restaurants dotted all over the city! 

St. Louis, Missouri 

With its mix of historic attractions, cultural and outdoor experiences, and good-old Midwestern hospitality, this welcoming city is perfect for a night’s stay. Visit the soaring Gateway Arch monument and take a tram to the top for gorgeous panoramic views over the Mississippi River before peeking into the Old Courthouse for a slice of local history. Embrace nature in the beautiful Forest Park, and don’t forget the stunning Missouri Botanical Garden for some peace amid the city sights. 

If the weather is hotting up, head for Ted Drewes Frozen Custard - the city’s famed dessert shop, which has been in operation since 1929. 

Amarillo, Texas 

Enter the Lone Star State and see horizons unfold in this vast playground of outdoor adventure, unique roadside art, and hearty all-American fare. Amarillo boasts a range of sights from the dramatic vistas at Palo Duro Canyon State Park to the quirky Cadillac Ranch, where 10 classic cars are buried nose-first into the ground and continuously spraypainted by passing visitors. 

The Route 66 Historic District is a great place for a bite to eat, people-watching, and to absorb the nostalgia of old-style America. If all that exploring has got you in the mood for food, hit up the Big Texan Steak Ranch and dare to attempt their enormous 72-ounce steak challenge! 

Flagstaff, Arizona 

The rugged beauty in and around Flagstaff can’t be overstated. It’s a place filled with natural wonders, cultural history, and plenty of outdoor activities. From the quaint Downtown area with its shops, restaurants, galleries and picturesque architecture to the otherworldly vibes at the Sunset Crater Volcano National Monument, it’s a place of contrasts and well worth a night or two.  

And of course, you can’t come all this way and not venture to the Grand Canyon! A 90-minute drive from Flagstaff will take you to the South Rim, or if you fancy taking the scenic (and longer) route, hop on the gorgeous Grand Canyon Railway at Williams for spectacular sights and a once-in-a-lifetime experience. 

Las Vegas, Nevada 

Sin City provides a wildly different change of pace. With its famous bright lights, glamorous hotels and casinos, and world-class cuisine, you can take in a show, hop on a night bus for a tour of the Strip, and indulge in everything this urban playground has to offer for a good few days of fun! 

Los Angeles, California 

End your journey in the Golden State! The official Route 66 finishes in Santa Monica, within the Los Angeles County, meaning you can spend a few days soaking up the sunshine and basking on some of the country’s most iconic beaches. Absorb the Hollywood lifestyle in LA with its upscale shopping, five-star dining, and landmark attractions such as the Hollywood Walk of Fame, Griffith Observatory, and a range of excellent museums. 

Our Accommodation Top Picks 

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Set in a perfect central location close to many of the city’s top attractions, this moderately priced hotel features an indoor pool and fitness centre, on-site restaurant, and comfortable rooms. 

Hotel Albuquerque at Old Town 

This landmark hotel is set in the heart of Albuquerque’s historic Old Town and the Sawmill District. Full of classic southwestern charm, this luxury property features an outdoor pool and hot tub, a wonderful Mexican restaurant and bar/lounge, as well as frequent nighttime entertainment. 

Little America Hotel, Flagstaff 

Positioned within 500 acres of ponderosa pine forest, this tranquil, lodge-style hotel ticks all the boxes for a true slice of rural American life. It boasts a seasonal outdoor swimming pool and spa, a great on-site dining option, and all the conveniences you’ll need during your night’s stay. 

Hotel Angeleno, Los Angeles 

This contemporary hotel is well placed in West Los Angeles and offers a complimentary buffet breakfast as well as fantastic panoramic views over the city from many of its rooms and public spaces. The rooftop restaurant, bar, and pool with fireplace terrace provide the perfect end-of-day spot for relaxation and fun after a long day exploring LA.  

Best Time to Visit 

May to early June is often considered the best time to travel Route 66 as the weather overall will be pleasantly warm but not too hot, with plenty of green landscapes to see, fewer crowds to tackle, and most attractions are up and running. The road conditions are much safer and quieter before the peak summer season, which makes roadside photography and exploring ideal. 

Another great option is to hit the road in early autumn between September and mid-October as the temperatures are milder after the hot summer months - particularly in the southwest - and there are fewer tourists, lower hotel rates, and beautiful changing scenery to admire. 

Our Comprehensive Car Hire 

We can provide a car to suit your budget, taste, and itinerary when travelling Route 66. And with every car hire booking, you’ll get these benefits included:  

• 24-hour roadside assistance  
• Comprehensive Insurance with our Gold Plus package, which features GPS, a full tank of fuel, underage driver fees, three additional drivers and child seats for your peace of mind  
• Quick and simple check-in online in minutes  
• Receive a virtual eSIM with 20GB of data, providing GPS navigation and more, whilst letting you keep your existing phone number 

Handy Tips 

Route 66 is considered one of the ultimate road trips, representing a slice of true 20th-century Americana. The journey is easily navigable to take at your own pace; however, it’s always a good idea to be prepared and plan for all eventualities, especially as you’ll travel through varied climates including deserts, plains, and mountainous areas. Here are some practical tips for your trip:  

• Plan your route but stay flexible by mapping out key stops and allowing for spontaneous detours or scenic pit stops  
• Keep updated on road and weather conditions before setting off each day  
• Pack layered clothing to accommodate for diverse climates across the states 
• Download offline maps just in case of unreliable signal in mountain and desert regions 
• Keep your petrol tank above halfway as it’s not unusual to drive long periods without coming across a place to fill up  
• Have cash ready for any toll roads  
• Drive during daylight hours for more visible conditions and the best views 
• Explore responsibly by respecting nature and leaving no trace i.e. don’t litter, stick to marked paths, and avoid feeding or touching wildlife  
• Keep hydrated and have plenty of snacks at the ready  
• Get an amazing road trip playlist downloaded!

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