Route 66 Road Trip: LA to Chicago

From €2599pp
Depart From
Fly from Cork, Shannon or Dublin
Departure Date
27 Dec 2023 - 11 Jan 2024
Other travel dates available
15 nights
From €2599pp
Enquire Now

Fly to Los Angeles and hit the 'Mother Road' through the heart of America, on this fantastic Route 66 Road Trip... including spending New Year's Eve in fabulous Las Vegas!

Route 66: small towns, gas stations, quaint old shops and retro motels- a once-in-a-lifetime-experience.

On arrival in Los Angles, collect your rental car and head to your home for the next two nights, the Gateway Hotel in Santa Monica. Located just 10 minutes from the airport and 5 minutes from the beach, this hotel blends coastal style with friendly service and plenty of thoughtful touches. It's the perfect place from which to begin your Route 66 adventure. At the end of Santa Monica pier, you'll find the roadmarker that traditionally marks the Western end of Route 66.

After 2 nights in Los Angeles, set off for Las Vegas. Located on the famous Las Vegas Strip, the Excalibur is a great base from which to explore this unique and lively city. This hotel's castle exterior promises fun and adventure- which is exactly what you'll find inside one of Las Vegas' most recognizable landmarks. You'll spend three nights here, including celebrating New Year's Eve in this unique and vibrant city.

On January 1st, hit the road again and head for the Grand Canyon. Marvel at the awe-inspiring scale of this natural wonder. You'll spend tonight at the Comfort Inn in the town of Williams, close to the Canyon. Want to take a tour while you're here? From hiking tours to helicopter tours, our experts can arrange the perfect Grand Canyon experience. Just let us know what you'd like to do!

The next day, continue on to Holbrook, Arizona. Though people have been living in this area for over 500 years, this small city was founded with the arrival of the railroads in the 1880s. Known in the indigenous language as Tʼiisyaakin, it is the county seat of Navajo County. You'll spend one night here, at the Baymont Inn & Suites. Located just off the I-40 this hotel offers a great breakfast, an indoor pool, and comfortable guestrooms. It's also just 25km from Petrified Forest National Park, where you can see ancient, petrified tree trunks and fossils. 

Your next stop will be Albuquerque, New Mexico. You'll spend two nights here, at the Doubletree by Hilton Hotel. Love museums? You'll be spoiled for choice here with the Museum of Natural History and Science, the Indian Pueblo Cultural Center and National Museum of Nuclear Science & History to name just a few. Thrillseekers will love a ride on the Sandia Peak Tramway up into the mountains. For an even better view, take off in a hot air ballon- an activity that Albuquerque is well-known for. 

Is this the way? Yes, the next stage of your Route 66 journey brings you to Amarillo, Texas. Tonight you'll stay at the Embassy Suites by Hilton. Guestrooms here area well-designed, with all modern amenities. There's an indoor pool, spa and fitness centre. A gateway to Palo Duro Canyon State Park, Amarillo's highlights include the iconic Cadillac Ranch and the beautiful botanical gardens. Texas is home to some of the best preserved sections of Route 66.

The next day, continue on to Oklahoma city. Known for its cowboy culture, your visit here must include some authentic local BBQ. Learn about the Wild West, the culture it fostered and its impact at the National Cowboy & Western Heritage Museum, American Banjo Museum and First Americans Museum. You'll spend one night at the lovely Sheraton Downtown. Oklahoma City Street Cars and Oklahoma City Museum of Art are both within an eight minute walk of the hotel.

St Louis, Missouri is your next destination. This city is probably best known for the iconic Gateway Arch, built in the 60's to honour the explorations Westward of Lewis & Clark. The view can be best enjoyed from one of the replica paddlewheelers which adorn the river. You'll stay just a 5-minute walk away, at the Drury Plaza at the Arch. Located in the heart of downtown Saint Louis, this the ideal place from which to explore the city. But it's not all about the Arch, other highlights include Busch Stadium (home of the Cardinals), Saint Louis Science Center, Grant's Farm, Forest Park and the City Museum.

After one night in St. Louis, continue your road trip to Springfield, Missouri. Famous as the origin of Highway 66, there's a placard to commemorate this on the east side of Park Central Square. Remnants of the old 66 Route run right through the city and can still be traced along many of the streets. Other sights here include the Air & Military Museum of the Ozarks, Trail of Tears National Historic Trail and the Wild Bill Hickok/ Davis Tutt shootout site. You'll spend one night in Springfield, at the Hilton Garden Inn.

The next day, continue along Route 66 to Chicago, Illinois. Return your hire car not far from your hotel, because you'll be spending the next two nights here in the city. Housed in a building dating back to the 1920's, the hip Saint Clair boutique hotel relaunched in September 2022 and provides a launchpad into the heart of Chicago close to the Magnificent Mile. With reimagined interior spaces, an art-inspired lobby, The Hot Coffee Shop and Curfew, the new restaurant operated by celebrity Chef Fabio Viviani, Hotel Saint Clair offers eccentric and distinctive spaces to work and gather for locals and travelers alike. Things to see in the Windy City include the Art Institute of Chicago, Millennium Park, Wrigley Field (home of the Chicago Cubs), Skydeck Chicago and the iconic Navy Pier. 

This itinerary is meant as a guide and can be adjusted to suit your particular needs. Want to stay in a different hotels? Extend your stay in certain towns? Reverse it and go Chicago- Los Angeles? Whatever your perfect Route 66 Road Trip looks like, we're here to make it happen. Chat to your USA experts to get started. 

December 27th - 29th: Los Angeles, California- 3* Gateway Hotel Santa Monica B&B 

December 29th- January 1st: Las Vegas, Nevada- 3* Excalibur Hotel Room only 

January 1st - 2nd: Grand Canyon (Williams, Arizona) - 3* Comfort Inn Near Grand Canyon Williams B&B

January 2nd - 3rd: Holbrook, Arizona- 3* Baymont Inn & Suites B&B

January 3rd - 5th: Albuquerque, New Mexico- 4* Doubletree by Hilton Hotel B&B

January 5th - 6th: Amarillo, Texas- 3* Embassy Suites by Hilton Downton Amarillo  B&B

January 6th - 7th: Oklahoma, Oklahoma- 4* Sheraton Downtown  B&B

January 7th - 8th: St Louis, Missouri- 3* Drury Plaza at the Arch B&B

January 8th - 9th: Springfield, Missouri 3* Hilton Garden Inn  B&B

January 9th - 11th: Chicago, Illinois- 4* Hotel Saint Clair Magnificent Mile Room Only

Price per person is based on 2 adults sharing, and includes:

  • Return flights from Cork, Dublin or Shannon via London
  • 23kg checked luggage
  • Car hire: SUV, Chevrolet or similar 27th Dec - 9th of Jan
  • 15 nights accommodation in selected 3* and 4* hotels:
    • Los Angeles, California- 3* Gateway Hotel Santa Monica B&B 
    • Las Vegas, Nevada- 3* Excalibur Hotel Room only 
    • Grand Canyon (Williams)- 3* Comfort Inn Near Grand Canyon Williams B&B
    • Holbrook, Arizona- 3* Baymont Inn & Suites B&B
    • Albuquerque, New Mexico- 4* Doubletree by Hilton Hotel B&B
    • Amarillo, Texas- 3* Embassy Suites by Hilton Downton Amarillo  B&B
    • Oklahoma, Oklahoma- 4* Sheraton Downtown  B&B
    • St Louis, Missouri- 3* Drury Plaza at the Arch B&B
    • Springfield, Missouri 3* Hilton Garden Inn  B&B
    • Chicago, Illinois- 4* Hotel Saint Clair Magnificent Mile Room Only

Please ask us about:

  • Travel insurance
  • ESTA visas
  • Attraction entry, guided tours and other experiences along Route 66. Save time and money by booking with us before you fly. From helicopter tours over the Grand Canyon to food tours around Chicago, we've got something for everyone.

Please be aware that a car hire fee of €107 is payable locally on arrival. Charges for car parking and road tolls are not included in your rental fee.

Subject to availability. Terms & conditions apply. This itinerary can be adjusted to suit your particular needs.

For more information please call us on 021 427 7094 or 01 696 5135, email, request a call back using the red button, or submit an enquiry through the form below.

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