Historic Route 66 Luxury Holidays
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Top Luxury holiday packages in Historic Route 66
- Hotel Saint Clair- Magnificent Mile
1 Oct - 6 OctHotel Saint Clair- Magnificent Mile + Flight
Downtown Chicago5 nights4.0 star property8.4/10 - Very good (2,100 reviews)Return • Dublin (DUB) - Chicago (ORD)DUB - ORD • 1 stop ORD - DUB • 1 stop£1,165£795found 1 hour agoper traveller - Hotel Riu Plaza Chicago
1 Oct - 6 OctHotel Riu Plaza Chicago + Flight
Downtown Chicago5 nights4.0 star property9.4/10 - Exceptional (4,942 reviews)Return • Dublin (DUB) - Chicago (ORD)DUB - ORD • 1 stop ORD - DUB • 1 stop - Four Seasons Hotel Chicago
9 Oct - 15 OctFour Seasons Hotel Chicago + Flight
Downtown Chicago6 nights5.0 star property9.4/10 - Exceptional (1,006 reviews)Return • London (LHR) - Chicago (ORD)LHR - ORD • Direct ORD - LHR • 1 stop - Level Chicago Fulton Market
1 Oct - 6 OctLevel Chicago Fulton Market + Flight
Downtown Chicago5 nights4.0 star property9.2/10 - Wonderful (546 reviews)"Great staff, great place!"Reviewed August 5, 2026Return • Dublin (DUB) - Chicago (ORD)DUB - ORD • 1 stop ORD - DUB • 1 stop - Sable at Navy Pier Chicago, Curio Collection by Hilton
9 Oct - 15 OctSable at Navy Pier Chicago, Curio Collection by Hilton + Flight
Downtown Chicago6 nights4.0 star property9.4/10 - Exceptional (2,644 reviews)"Great beautiful rooms. Nice beds"Reviewed August 7, 2026Return • London (LHR) - Chicago (ORD)LHR - ORD • Direct ORD - LHR • 1 stop
Top Luxury Historic Route 66 Hotels
Quality Inn Holbrook near Petrified Forest
Quality Inn Holbrook near Petrified Forest"Older hotel but flooring was new LVP. Ice machine near front was convenient. Front desk--at check in and check out/breakfast were pleasant."
Ramada by Wyndham Williams/Grand Canyon Area
Ramada by Wyndham Williams/Grand Canyon Area"The beds were comfortable and room was clean pool area also great. Loved the big parking lot to park our truck that was pulling a trailer"
Americas Best Value Inn & Suites Flagstaff
Americas Best Value Inn & Suites Flagstaff"Good"
The L Motel - Downtown Flagstaff
The L Motel - Downtown Flagstaff
Days Inn by Wyndham St. Robert Waynesville/Ft. Leonard Wood
Days Inn by Wyndham St. Robert Waynesville/Ft. Leonard Wood"Missed not having a complimentary breakfast"
Terrace #1 | 2 BR/1BA | Spend Spring in Flagstaff!
Terrace #1 | 2 BR/1BA | Spend Spring in Flagstaff!"This stay was AWESOME ! The beds were so comfortable, the home was immaculate.m and we felt so incredibly safe so close to Downtown. We had the pleasure of staying here with our puppy and the accessibility to the backyard was absolutely fantastic. Our stay was met with calm and serene every time we stepped foot in the door. Everything that we wanted to explore was walking distance. The host responded quickly with any questions we had. "
Terrace Main | 5BR/3BA | Spend Spring in Flagstaff!
Terrace Main | 5BR/3BA | Spend Spring in Flagstaff!"The house was ok. There was an issue with the outlets not working in one room, the dishwasher was not secured and would fall forward when the trays were pulled out, and one of the pans in the kitchen needs to be replaced. Other than that, it was fine."
All you need to know about luxury holidays in Historic Route 66
What can I expect from a luxury Historic Route 66 holiday?
Luxury on holiday is all about relaxing and feeling good. Whether you choose a sumptuous spa, Michelin-starred restaurant or super-king bed is your call. Use our amenities filters to find the things that tick all your boxes.
How can I find all-inclusive luxury holidays in Historic Route 66?
Tick the all-inclusive and 5-star filters to find the crème de la crème of Historic Route 66 holidays. With everything included in the package price, you can drink and dine to your heart’s content, without worrying about that bill at the end.
Can I book a cheap luxury holiday to Historic Route 66?
A luxury holiday doesn’t have to break the bank. Travel out of peak season, choose a hotel or resort a little way out or go for a last-minute getaway and you’ll find some cracking deals. Sort by price to find luxury holidays to Historic Route 66 starting at £795. Prices and availability are subject to change. Additional terms may apply.
Are there luxury spa holidays in Historic Route 66?
For sunset massages on the shoreline and view-filled saunas, use our spa filter to find your ideal Historic Route 66 spa hotel. Book a whole weekend soaking away your stresses, or hop into the spa after the beach, some golf or a local advent-ahhhh.
What should I look for when booking a luxury family holiday in Historic Route 66?
Luxury isn’t just for adults. Those little touches designed for little people make a family holiday genuinely stress free … which is the greatest luxury of all. Look for spacious suites, pools toddlers can splash in, and breakfast buffets with waffles, pancakes and Nutella galore.
Can I book luxury last-minute holidays to Historic Route 66?
You can wangle a top-notch luxury holiday in Historic Route 66 for a fraction of the normal price by booking last minute. Just enter your dates and see what’s available – if you’re flexible ... even better!
Can I book a luxury holiday in Historic Route 66 with free cancellation and/or flexible dates?
If you’re splashing out on a luxury holiday, make sure your money is safe by booking with free cancellation. Just use the fully refundable filter and make sure you read all the terms and conditions.
Why should I book my luxury travel to Historic Route 66 with Expedia?
Nobody does luxury quite like Expedia. With so many gorgeous properties in Historic Route 66 to choose from, as well as access to first-class flight deals and hire cars with horsepower, there’s no better place to book.