Historic Route 66 Mountain Holidays
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Top flight + Mountain hotel deals in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Silversmith Hotel Chicago Downtown
Downtown Chicago
£1,013
per person
21 Dec - 28 Dec
found 4 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (2,414 reviews)
Hotel Silversmith was in the exact location I was hoping for!
The staff was so friendly and helpful and I had pleasant interactions with them every time. They were also very honest about what kinds of things would improve my stay (such as taking the bus instead of the train), which as an out-of-towner, I really appreciated.
I stayed in the standard King Room and it was really great. My only knit-pick is that while the room had a mini fridge, there was no microwave. Otherwise, perfect. I would absolutely stay here again!
Reviewed on 12 Oct 2026
Eurostars Magnificent Mile
Downtown Chicago
£1,047
per person
21 Dec - 28 Dec
found 6 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9/10 Wonderful! (3,934 reviews)
Hands-down, always my favorite place to stay when I am in Chicago. I’ve been staying here for years. It’s essentially located so you can walk everywhere to the magnificent mile to the Gold Coast Beach to all of the shopping. Restaurants are right next to it. There is a true food, kitchen and a soul cycle right next to it as well and Tal nightclub is also right next-door. The staff is absolutely amazing in the rooms are luxurious for a great price.
Reviewed on 12 Oct 2026
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View all trips5* Mountain holidays in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago
Downtown Chicago
£1,331
per person
19 Dec - 22 Dec
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Service was superb. However, the mattress was too soft for me. The comforter has a bloody spot on it that should have been replaced.
Reviewed on 12 Oct 2026
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View all trips3 Night Mountain holidays in Historic Route 66
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Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
£925
per person
19 Dec - 22 Dec
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,727 reviews)
This is the only property right on Navy Pier! We were able to get many places with the help of public transportation!
And it had a great view!
Reviewed on 12 Oct 2026
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View all trips4 Night Mountain holidays in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
