
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
Price was ¥310,404, price is now ¥260,047 per person
¥260,047
per person
Apr 15 - Apr 18
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026

Waldorf Astoria Chicago
Downtown Chicago
Price was ¥315,934, price is now ¥266,546 per person
¥266,546
per person
Apr 15 - Apr 18
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026


River Spirit Casino Resort
South Tulsa
Price was ¥316,599, price is now ¥305,052 per person
¥305,052
per person
Apr 29 - May 2
found 1 day ago
Roundtrip flight included
Fukuoka (FUK) to Tulsa (TUL)
9.4/10 Exceptional! (2,516 reviews)
I've stayed at this resort several times, the customer service is always excellent, the rooms are impeccably clean and spacious.
I also enjoy the concert venue, the Cove, a great deal.
That said, if you're coming to gamble, you may find that the slots favor the house more than other casinos in the area.
Reviewed on Feb 9, 2026

DoubleTree by Hilton Tulsa - Warren Place
South Tulsa
Price was ¥320,394, price is now ¥310,260 per person
¥310,260
per person
Apr 29 - May 2
found 1 day ago
Roundtrip flight included
Fukuoka (FUK) to Tulsa (TUL)
8.2/10 Very Good! (617 reviews)
Hotel was decent. We had an issue with our shower not draining, had to stop the water mid shower to let it drain so you could finish the shower without it overflowing onto the floor. Also, mattress had a big hole toward the middle. Seemed like time for a new mattress. Other than that it was good
Reviewed on Feb 1, 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
Price was ¥310,404, price is now ¥260,047 per person
¥260,047
per person
Apr 15 - Apr 18
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026

Waldorf Astoria Chicago
Downtown Chicago
Price was ¥315,934, price is now ¥266,546 per person
¥266,546
per person
Apr 15 - Apr 18
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026

Don't see what you're looking for?
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View all trips3 Night Romantic vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.

River Spirit Casino Resort
South Tulsa
Price was ¥316,599, price is now ¥305,052 per person
¥305,052
per person
Apr 29 - May 2
found 1 day ago
Roundtrip flight included
Fukuoka (FUK) to Tulsa (TUL)
9.4/10 Exceptional! (2,516 reviews)
I've stayed at this resort several times, the customer service is always excellent, the rooms are impeccably clean and spacious.
I also enjoy the concert venue, the Cove, a great deal.
That said, if you're coming to gamble, you may find that the slots favor the house more than other casinos in the area.
Reviewed on Feb 9, 2026


DoubleTree by Hilton Tulsa - Warren Place
South Tulsa
Price was ¥320,394, price is now ¥310,260 per person
¥310,260
per person
Apr 29 - May 2
found 1 day ago
Roundtrip flight included
Fukuoka (FUK) to Tulsa (TUL)
8.2/10 Very Good! (617 reviews)
Hotel was decent. We had an issue with our shower not draining, had to stop the water mid shower to let it drain so you could finish the shower without it overflowing onto the floor. Also, mattress had a big hole toward the middle. Seemed like time for a new mattress. Other than that it was good
Reviewed on Feb 1, 2026
Don't see what you're looking for?
See all available trips from Fukuoka 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.


Shangri-La Resort
Price was ¥330,837, price is now ¥322,188 per person
¥322,188
per person
Mar 20 - Mar 24
found 23 hours ago
Roundtrip flight included
Tokyo (TYO) to Tulsa (TUL)
9/10 Wonderful! (287 reviews)
Room was in good condition. Didn't stay long enough to review much more than that.
Reviewed on Jan 20, 2026

Holiday Inn Express & Suites Vinita by IHG
Price was ¥347,846, price is now ¥343,369 per person
¥343,369
per person
Mar 20 - Mar 24
found 23 hours ago
Roundtrip flight included
Tokyo (TYO) to Tulsa (TUL)
8.4/10 Very Good! (391 reviews)
Friendly and helpful staff, good breakfast, nice room.
Reviewed on Dec 27, 2025
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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.
