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.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥456,116
per person
Nov 14 - Nov 20
found 21 hours 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.
Four Seasons Hotel Chicago
Downtown Chicago
￥384,460
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Perfect location for shopping, beach, and restaurants. Very clean and staff is very friendly… did not disappoint. Everything met the mark and expectations of a Four Seasons.
Reviewed on Sep 2, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
￥456,116
per person
Nov 14 - Nov 20
found 21 hours 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 Fukuoka 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.
Hotel Riu Plaza Chicago
Downtown Chicago
￥284,972
per person
Nov 30 - Dec 2
found 1 day 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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See all available trips from Fukuoka to Historic Route 66
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
￥346,254
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip 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
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.
