Historic Route 66 Ski Holidays
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Top Ski holiday packages in Historic Route 66
- Hotel Felix River North/Magnificent Mile
29 Dec - 3 JanHotel Felix River North/Magnificent Mile + Flight
Downtown Chicago5 nights4.0 star property8.4/10 - Very good (3,187 reviews)"Charged for an extra night that we didn’t stay and called and was told a reimbursement was completed. Five days later, the full charge for the night we didn’t stay posted in my account and with no reimbursement. When I called again, was told there was nothing they could do because the reimbursement was “released” and I would have to wait to talk to a manager when they arrived which would not be until the nighttime hours."Reviewed November 14, 2026Return • Dublin (DUB) - Chicago (ORD)DUB - ORD • Direct ORD - DUB • Direct€1,271€1,046found 6 hours agoper traveller - Hotel Saint Clair- Magnificent Mile
29 Dec - 3 JanHotel Saint Clair- Magnificent Mile + Flight
Downtown Chicago5 nights4.0 star property8.6/10 - Excellent (2,413 reviews)Return • Dublin (DUB) - Chicago (ORD)DUB - ORD • Direct ORD - DUB • Direct€1,472€1,113found 6 hours agoper traveller - Swissotel - Chicago
29 Dec - 3 JanSwissotel - Chicago + Flight
Downtown Chicago5 nights4.5 star property9.0/10 - Wonderful (3,585 reviews)"LOVE this hotel! Location is perfect and you can walk everywhere! Just wished they had a pool"Reviewed November 14, 2026Return • Dublin (DUB) - Chicago (ORD)DUB - ORD • Direct ORD - DUB • Direct€1,507€1,213found 6 hours agoper traveller - Sports Illustrated Resorts Chicago
29 Dec - 3 JanSports Illustrated Resorts Chicago + Flight
Downtown Chicago5 nights3.5 star property9.0/10 - Wonderful (1,541 reviews)"Very clean and comfortable. Valet was helpful and kind"Reviewed November 13, 2026Return • Dublin (DUB) - Chicago (ORD)DUB - ORD • Direct ORD - DUB • Direct€1,367€1,116found 6 hours agoper traveller - InterContinental Chicago Magnificent Mile by IHG
29 Dec - 3 JanInterContinental Chicago Magnificent Mile by IHG + Flight
Downtown Chicago5 nights4.5 star property9.2/10 - Wonderful (3,428 reviews)Return • Dublin (DUB) - Chicago (ORD)DUB - ORD • Direct ORD - DUB • Direct€1,399€1,159found 6 hours agoper traveller
Top Ski Historic Route 66 Hotels
Ramada by Wyndham Williams/Grand Canyon Area
Ramada by Wyndham Williams/Grand Canyon Area"Our room was ok. The shower faucet and spout was very loose and not secured. The pocket door to the bathroom was noisy and hard to close."
Americas Best Value Inn & Suites Flagstaff
Americas Best Value Inn & Suites Flagstaff
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 €1,046, 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.