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Linking Chicago, Illinois, to Los Angeles, California, U.S. Route 66 runs 3,940 kilometres, allowing travellers to see several major landmarks and monuments and explore some national parks. There’s no better way to taste U.S. tradition and road trip lore than along this much-loved byway. Pack your camera, sunscreen and shades, and enjoy the views.

Itinerary Highlights

  • Drive at your own pace
  • Explore National Parks
  • Journey through historic old town districts
  • Spend time on the mighty Mississippi

What’s included

  • Rental Car included
  • Meet & greet airport service
  • Luxury or boutique accommodation at your chosen level
  • Expert guides in select destination


This is an example itinerary. It is fully flexible; you can add or detract days and include hotels at your chosen budget. It departs daily.



Price Guide


Our quotes are bespoke for your customised trip. The prices displayed are indicative only, read more

Day 1

Fly to Chicago

plan line
Day 2

Chicago, Illinois

Fly into Chicago’s O’Hare International Airport and drive your rental car to the official “Begin” sign for Route 66, which lies on East Adams Street, west of the intersection with South Michigan Avenue. For commemorative photos, however, check out the more artistic sign, complete with a colourful map, placed in a small fenced park at Adams and Wabash streets. Before you hop on the road, make the most of Chicago by visiting the “Cloud Gate” sculpture, more commonly known as “The Bean.” This public sculpture is the centrepiece of Millennium Park. Take a Chicago architecture tour by boat to see some of the city’s major landmarks and enjoy the iconic skyline.

As you head to St. Louis, Missouri, make a pit stop at the Route 66 Association Hall of Fame and Museum in Pontiac, Illinois, about 161 kilometres southwest of Chicago. While there, check out the Route 66 Mural and other memorabilia.

Day 3-4

St. Louis, Missouri

Along the way to St. Louis, you’ll find a host of famous motels, museums, drive-in restaurants and breakfast hot spots. It’s impossible to miss the 192-meter-tall Gateway Arch; be sure to take a trip to the top of this stainless steel landmark — also known as the “Gateway to the West” — for breathtaking city views.

Get a taste of sports culture with a trip to Busch Stadium, home of the St. Louis Cardinals Major League Baseball team. Visit the Anheuser-Busch Brewery and take a tour. Check out the Chain of Rocks Bridge on the city’s northern edge, which crosses the Mississippi River. Part of Route 66 for several decades, the old bridge has since been turned into a landmark, bikeway and trail system on both sides of the river.

Day 5-6

Oklahoma City, Oklahoma

Your introduction to Oklahoma City is all about food. Pops 66 Soda Ranch, a landmark diner and gas station in Arcadia, serves 700 hundred kinds of sodas, burgers, sandwiches, meatloaf and other comfort foods. Just look for the 21-meter-tall soda bottle out front. Or try one of the many barbecue spots in the area, including Jack’s Bar-B-Q and Jigg’s Smokehouse.

Digest at nearby Lake Hefner with a few hours of birdwatching and fishing. And for a little local culture, take a trip to The Womb Art Center. Founded by Flaming Lips frontman Wayne Coyne, this mural-splashed gallery features all kinds of psychedelic artwork and should provide plenty of conversation for the miles ahead.

Day 7-8

Amarillo, Texas

Amarillo boasts a historic district listed on the U.S. National Register of Historic Places. The U.S. Route 66-Sixth Street Historic District is a 13-block development, home to several commercial buildings built in the Spanish Revival, Art Deco and Art Moderne styles and a hub for socializing and entertainment. Meet and mingle with locals at the historic – and rumoured to be haunted – Natatorium building, now converted into an antique emporium.

Also, visit the famous Cadillac Ranch in Amarillo, an art installation that features several Cadillac car sculptures with their noses buried in the ground. Not to be outdone, VW Slug Bug Ranch in Conway, Texas, features five Volkswagen Beetles.

Day 9-10

Albuquerque, New Mexico

Before you get to Albuquerque, be sure to check out the Blue Hole, a bell-shaped blue pool east of Santa Rosa, New Mexico — a popular spot for scuba diving and relaxation. Once within the city limits, you can’t miss the historic neon signs that light up Old Route 66. Albuquerque has a historic Old Town district and many great restaurants, shops and boutiques. Travellers travelling down Central Avenue marvel at the vintage signs adorning the storefronts. Tuck into traditional diner food at the whimsical 66 Diner on Central Avenue Northeast. Bring your appetite; this place serves up Fiesta Fries smothered in Texas chilli and whole-milk milkshakes.

Day 11-12

Holbrook, Arizona

Littered with Route 66 signs, Holbrook, Arizona, is home to legendary motels and classic diners serving Tex-Mex-style cuisine. It’s easy to take a step back in time driving on this town’s main strip. You can’t miss the Wigwam Village Motel with 15 freestanding concrete teepees. Holbrook has earned a reputation for its quirky rock shops and dinosaur statues. Check out the brightly painted dinosaur statues downtown before heading to Petrified Forest National Park. You’ll need at least a day in this Painted Desert park, which features spectacular backcountry hikes and group activities, such as backpacking, ranger-guided tours and birdwatching.

Day 13-14

Los Angeles, California

Finish your road trip at the Santa Monica Pier in Los Angeles, California, the official end of Route 66. Los Angeles, otherwise known as the City of Angels, is home to Old Route 66, which runs from Olvera Street and El Pueblo de Los Angeles Historical Monument to West Hollywood. There, it turns into Santa Monica Boulevard.

A popular destination for sunbathing, dining and amusement park lovers, Santa Monica State Beach features a bike path and is also home to the Original Muscle Beach. Visit the Heal the Bay Aquarium, see the historic 1922 Looff Hippodrome Carousel or shop the pedestrian-only Third Street Promenade. If people-watching is more your thing, head 15 minutes south to one of the most visited sites in Southern California, the Venice Beach Boardwalk. Or, enjoy First Fridays at Abbot Kinney Boulevard when food trucks and entertainment take over the street. Either way, you’ll get a superb taste of California living before flying home from Los Angeles International Airport (LAX).

dot joiner for itins
Day 15

Fly home

A note on price

The prices outlined above are a rough guide to give you an idea of costs and enable you to budget for your trip.

Guide prices are generally for private arrangements based on twin share, in well located, good quality accommodation (excluding international flights).

Please note costs are indicative and may vary due to a number of factors such as; travel date, hotel choice, room category, number of people travelling and prevailing exchange rates.

Price Guide TBC

When to travel

jan feb mar apr may jun jul aug sep oct nov dec

The weather across the United States varies greatly depending on the region you plan to visit. In general, the summer months tend to be hot and humid in the south, while the west experiences dry heat. The northeast can be milder with occasional rain showers. However, it’s important to always check the weather forecast before traveling to ensure you are prepared for any unexpected changes. Regardless of the weather, there are plenty of exciting destinations to explore in the USA, from the beaches of Florida to the mountains of Colorado.

Add on’s

There are a multitude of add-on holiday options to this USA itinerary, for example, you could head North to San Fransisco take a detour and head deeper into Texas or visit the Grand Canyon in Arizona.

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