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.
Thompson Chicago, by Hyatt
Downtown Chicago
Price was ￥419,910, price is now ￥349,994 per person
￥349,994
per person
May 29 - Jun 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,326 reviews)
Room was nice and clean, decent view.
Perfect location. Close to shopping and nice restaurants.
Staff was amazing; Myron in particular was so kind and accommodating.
Reviewed on Mar 8, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥505,796, price is now ￥391,960 per person
￥391,960
per person
May 28 - Jun 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Great spot and view, would stay again!
Reviewed on Mar 13, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥468,384, price is now ￥369,362 per person
￥369,362
per person
Jun 5 - Jun 8
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Comfy beds, great staff, great shower, great breakfast
Reviewed on Mar 13, 2026
Hilton Chicago
Downtown Chicago
Price was ￥605,910, price is now ￥499,852 per person
￥499,852
per person
May 28 - Jun 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (2,675 reviews)
It is a very old hotel that is very well maintained.
Room temperature is controlled by maintenance.
Reviewed on Mar 12, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥415,929, price is now ￥356,362 per person
￥356,362
per person
May 29 - Jun 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,646 reviews)
Great room but the beds were really small. The bathroom door was frosted but you could still see through the door and there was a large mirror in front of the bathroom door. To top it off the bathroom door was a sliding door that did not close all the way, so absolutely no privacy in a room that sleeps 4!
Reviewed on Mar 13, 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.
The Ritz-Carlton, St. Louis
Clayton
Price was ￥582,318, price is now ￥574,602 per person
￥574,602
per person
May 1 - May 5
found 22 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to St. Louis (STL)
9.2/10 Wonderful! (557 reviews)
Excellent staff! I was upgraded to a deluxe room from a standard at check-in. Servers and bartenders were kind and helpful and the food and drinks were delicious.
Reviewed on Mar 13, 2026
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View all trips3 Night Luxury vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥402,090, price is now ￥327,374 per person
￥327,374
per person
May 29 - Jun 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Great spot and view, would stay again!
Reviewed on Mar 13, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥468,384, price is now ￥369,362 per person
￥369,362
per person
Jun 5 - Jun 8
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Comfy beds, great staff, great shower, great breakfast
Reviewed on Mar 13, 2026
Thompson Chicago, by Hyatt
Downtown Chicago
Price was ￥419,910, price is now ￥349,994 per person
￥349,994
per person
May 29 - Jun 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,326 reviews)
Room was nice and clean, decent view.
Perfect location. Close to shopping and nice restaurants.
Staff was amazing; Myron in particular was so kind and accommodating.
Reviewed on Mar 8, 2026
Don't see what you're looking for?
See all available trips from Tokyo 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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥505,796, price is now ￥391,960 per person
￥391,960
per person
May 28 - Jun 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Great spot and view, would stay again!
Reviewed on Mar 13, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥574,240, price is now ￥402,408 per person
￥402,408
per person
May 28 - Jun 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Comfy beds, great staff, great shower, great breakfast
Reviewed on Mar 13, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥528,000, price is now ￥412,964 per person
￥412,964
per person
May 28 - Jun 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
Loved how it was next to all the things you might need during a stay A grocery store convenience store and even a Walgreens down the street
Reviewed on Mar 12, 2026
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See all available trips from Tokyo to Historic Route 66
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
