Historic Route 66 Romantic Vacations
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Top Romantic vacation packages in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥328,376
per person
Dec 26 - Dec 30
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
This is one of the best Trump properties I've been to.
I know Trump Hotels' bar is high, but this is on another level.
Obviously, being a landmark in Chicago, location is the best in Chicago.
There is a Langham property right next to it, but this is it.
Rooms are well maintained, and the restaurants were excellent.
I hope to visit again soon.
Reviewed on Oct 12, 2026
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View all trips5* Romantic vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥328,376
per person
Dec 26 - Dec 30
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
This is one of the best Trump properties I've been to.
I know Trump Hotels' bar is high, but this is on another level.
Obviously, being a landmark in Chicago, location is the best in Chicago.
There is a Langham property right next to it, but this is it.
Rooms are well maintained, and the restaurants were excellent.
I hope to visit again soon.
Reviewed on Oct 12, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Historic Route 66
View all trips4 Night Romantic vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥328,376
per person
Dec 26 - Dec 30
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
This is one of the best Trump properties I've been to.
I know Trump Hotels' bar is high, but this is on another level.
Obviously, being a landmark in Chicago, location is the best in Chicago.
There is a Langham property right next to it, but this is it.
Rooms are well maintained, and the restaurants were excellent.
I hope to visit again soon.
Reviewed on Oct 12, 2026
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.
