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
Price was ￥379,200, price is now ￥302,369 per person
￥302,369
per person
Feb 21 - Feb 25
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The property was beautiful. The holiday decorations were magical. The staff was friendly and helpful.
Reviewed on Dec 1, 2025
Level Chicago – Old Town
Downtown Chicago
Price was ￥320,168, price is now ￥261,760 per person
￥261,760
per person
Feb 19 - Feb 23
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Its room was perfect the only bad part was their was a couple stains in the bathroom wall
Reviewed on Dec 1, 2025
The Peninsula Chicago
Downtown Chicago
Price was ￥419,270, price is now ￥343,284 per person
￥343,284
per person
Feb 19 - Feb 23
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Excellent service throughout the hotel
Reviewed on Nov 29, 2025
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See all available trips from Tokyo to Historic Route 66
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
Price was ￥379,200, price is now ￥302,369 per person
￥302,369
per person
Feb 21 - Feb 25
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The property was beautiful. The holiday decorations were magical. The staff was friendly and helpful.
Reviewed on Dec 1, 2025
The Peninsula Chicago
Downtown Chicago
Price was ￥419,270, price is now ￥343,284 per person
￥343,284
per person
Feb 19 - Feb 23
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Excellent service throughout the hotel
Reviewed on Nov 29, 2025
Nobu Hotel Chicago
Downtown Chicago
Price was ￥379,688, price is now ￥348,893 per person
￥348,893
per person
Jan 17 - Jan 21
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (748 reviews)
The sink clogged at some point the staff was not that attentive
Reviewed on Nov 29, 2025
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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.
Level Chicago – Old Town
Downtown Chicago
Price was ￥320,168, price is now ￥261,760 per person
￥261,760
per person
Feb 19 - Feb 23
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Its room was perfect the only bad part was their was a couple stains in the bathroom wall
Reviewed on Dec 1, 2025
Chicago luxury home suites
Downtown Chicago
Price was ￥577,256, price is now ￥439,498 per person
￥439,498
per person
Feb 19 - Feb 23
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
10/10 Exceptional! (1 review)
Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job.
Reviewed on Nov 26, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥379,200, price is now ￥302,369 per person
￥302,369
per person
Feb 21 - Feb 25
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The property was beautiful. The holiday decorations were magical. The staff was friendly and helpful.
Reviewed on Dec 1, 2025
Don't see what you're looking for?
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.
