Historic Route 66 Luxury Vacations
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Top Luxury vacation packages in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
The Hacienda & Spa at Hotel Santa Fe
Downtown Santa Fe
￥352,905
per person
Oct 28 - Nov 2
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Albuquerque (ABQ)
9.4/10 Exceptional! (1,000 reviews)
Welcoming and helpful staff. My boys enjoyed the continental breakfast every morning while mom enjoyed the complementary happy hour in the evenings. The suite was spacious.
Awesome location. Although half the hotel is unavailable and there is no restaurant on site currently. There are great restaurants in walking distance. The pool is unheated and hot tub is out of order. The pool area could use some tlc.
Reviewed on Sep 3, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
￥456,116
per person
Nov 14 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
The Trump Hotel In Chicago is one of my family's FAVORITE hotels in the world. We stay at The Trump every single time we're in Chicago. It's the BEST.😀👍
Reviewed on Sep 2, 2026
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View all trips5* Luxury vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥456,116
per person
Nov 14 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
The Trump Hotel In Chicago is one of my family's FAVORITE hotels in the world. We stay at The Trump every single time we're in Chicago. It's the BEST.😀👍
Reviewed on Sep 2, 2026
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See all available trips from Osaka to Historic Route 66
View all trips3 Night Luxury vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Eurostars Magnificent Mile
Downtown Chicago
￥263,859
per person
Nov 30 - Dec 2
found 12 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9/10 Wonderful! (3,865 reviews)
I stayed a weekend at the hotel and upon entering there is a restaurant. The hotel check in is upstairs. I’m not a fan of that setup because I was confused as to where to go when my Lyft dropped me off.
The staff is very nice and friendly. They interacted with guests in passing. In my room there was noticeable wear and tear. Overall the room was clean.
I used the spa. You have to book with them for them to open the spa. It seems like a company rents the space out and comes to service you as needed. I enjoyed my spa experience.
Lastly, the restaurant was okay. It didn’t have enough variety for me but the tomato soup and cheesecake I enjoyed.
Reviewed on Sep 3, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
￥282,669
per person
Nov 30 - Dec 2
found 12 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (5,106 reviews)
We absolutely loved this hotel. My wife and I came for two days to celebrate my birthday. The location is fantastic to walk many great places, breakfast buffet was the best, excellent selection and tasty. While eating breakfast then brought me a birthday brownie and put chocolate in our room. Above and beyond expectations. Very clean and modern hotel with great staff. Roof top bar is a must!
Reviewed on Sep 2, 2026
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View all trips4 Night Luxury vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
￥391,422
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (5,106 reviews)
We absolutely loved this hotel. My wife and I came for two days to celebrate my birthday. The location is fantastic to walk many great places, breakfast buffet was the best, excellent selection and tasty. While eating breakfast then brought me a birthday brownie and put chocolate in our room. Above and beyond expectations. Very clean and modern hotel with great staff. Roof top bar is a must!
Reviewed on Sep 2, 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
￥366,054
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
The room was very clean and spacious. Staff was very informative about what was accessible during our stay. I would definitely stay here again if I come back to visit Chicago.
Reviewed on Sep 1, 2026
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View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
