Historic Route 66 Luxury Holidays
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Top Luxury holiday packages in Historic Route 66
- Eurostars Magnificent Mile
8 Oct - 14 OctEurostars Magnificent Mile + Flight
Downtown Chicago6 nights4.0 star property9.0/10 - Wonderful (3,786 reviews)Return • Athens (ATH) - Chicago (ORD)ATH - ORD • Direct ORD - ATH • Direct€2,924€2,061found 1 day agoper traveller - Sable at Navy Pier Chicago, Curio Collection by Hilton
8 Oct - 14 OctSable at Navy Pier Chicago, Curio Collection by Hilton + Flight
Downtown Chicago6 nights4.0 star property9.4/10 - Exceptional (2,643 reviews)"Great rescpatio "Reviewed August 5, 2026Return • Athens (ATH) - Chicago (ORD)ATH - ORD • Direct ORD - ATH • Direct€3,026€2,065found 1 day agoper traveller - L7 Chicago by LOTTE
8 Oct - 14 OctL7 Chicago by LOTTE + Flight
Downtown Chicago6 nights4.5 star property9.6/10 - Exceptional (4,509 reviews)"The staff was super friendly and helpful. Very nice ambience, and the bar downstairs was great."Reviewed August 6, 2026Return • Athens (ATH) - Chicago (ORD)ATH - ORD • Direct ORD - ATH • Direct€2,701€2,117found 1 day agoper traveller - Pendry Chicago
8 Oct - 14 OctPendry Chicago + Flight
Downtown Chicago6 nights4.5 star property9.2/10 - Wonderful (1,147 reviews)Return • Athens (ATH) - Chicago (ORD)ATH - ORD • Direct ORD - ATH • Direct€3,881€3,118found 1 day agoper traveller - Silversmith Hotel Chicago Downtown
8 Oct - 14 OctSilversmith Hotel Chicago Downtown + Flight
Downtown Chicago6 nights4.0 star property9.4/10 - Exceptional (2,314 reviews)"I was impressed with the friendliness of staff, very comfy bed, nice big shower, clean updated hotel. They always are happy to give you more bottled water for the room which I really appreciated! My food for breakfast from the restaurant was great and reasonably priced.The restaurant staff was to notch!! I would stay here again without any hesitation."Reviewed August 5, 2026Return • Athens (ATH) - Chicago (ORD)ATH - ORD • 1 stop ORD - ATH • 1 stop€6,561€5,537found 18 hours agoper traveller
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
Americas Best Value Inn & Suites Flagstaff
Americas Best Value Inn & Suites Flagstaff"Good"
The L Motel - Downtown Flagstaff
The L Motel - Downtown Flagstaff"Just the ice machine didn’t always have ice"
Days Inn by Wyndham St. Robert Waynesville/Ft. Leonard Wood
Days Inn by Wyndham St. Robert Waynesville/Ft. Leonard Wood"Clean room and comfortable stay"
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."
Frequently Asked Questions
How much does a Historic Route 66 holiday package cost?
Our Historic Route 66 packages, which start at just €2,061, are an easy way to save big bucks. Pick your preferred flights, hotels and rental cars to create your ideal trip.
How do I get a cheap travel package to Historic Route 66?
Book everything all in one place with our Historic Route 66 holiday packages. We have incredible bargains on hotels, flights and more that'll keep your hip pocket happy and your adventurous spirit alive. And, with more than 550 airlines and 1,000,000 properties globally to select from, you'll have the flexibility to mix and match as you please.
What are the top hotels in Historic Route 66?
If you're headed to Gillespie, you can't go past Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton. Both are excellent bases for exploring this lively Historic Route 66 city.
How far in advance should I book my Historic Route 66 holiday?
The earlier you book, the better. Airlines usually release flight tickets nearly 12 months prior to departure, and this is a fantastic opportunity to pick up some of the lowest prices. Just been told you need to take your holiday time next month? That's alright! Expedia are never short of fantastic deals to send you off on the getaway of your dreams, at a price you can afford.
What does an Expedia Historic Route 66 travel package include?
You can select from a combination of hotels, flights and rental cars. Once you've made your booking, you can add the fun stuff like activities and experiences. Want to pick your fare class? That's possible too. The choice is all yours when it comes to crafting your dream Historic Route 66 getaway.
What should I know before booking a Historic Route 66 travel package?
An Expedia travel package can be tailored to your budget and is a fantastic way to make your hard-earned dollars stretch further. How little or much you include is totally up to you. Hotels, rental cars and flights — come up with a combination that suits your plans.
Can I choose my airline with a Historic Route 66 Expedia holiday package?
Yes, definitely. Expedia has more than 550 airline partners to pick from around the globe. With such a big range of choice, finding the perfect carrier to take you to Historic Route 66 shouldn't be hard.
If I'm not able to travel, can I cancel my Historic Route 66 holiday package?
You sure can, and we're here to help. You may be able to cancel or change your Historic Route 66 holiday package for free if you booked in the last 24 hours. However, you may be charged a fee by your airline, hotel or car rental company if you booked more than 24 hours ago. If life gets in the way of your holiday, take a look at our Customer Service Portal for more information.