Historic Route 66 Romantic Vacations
Book a Romantic Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Romantic vacation packages in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ￥323,468, price is now ￥275,784 per person
￥275,784
per person
Feb 22 - Feb 27
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Overall good experience. My room was not cleaned one of the nights because the maid didn’t come until late but we were already in our room. Also, the $25/night resort fee was not properly explained to me, didn’t make much sense at all honestly. Property is nice and in a great location but i wouldn’t stay here again
Reviewed on Dec 19, 2025
The Peninsula Chicago
Downtown Chicago
Price was ￥478,845, price is now ￥375,622 per person
￥375,622
per person
Feb 22 - Feb 27
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Service and clean room - paying attention to the details
Reviewed on Dec 22, 2025
Level Chicago – Old Town
Downtown Chicago
Price was ￥340,795, price is now ￥286,280 per person
￥286,280
per person
Feb 22 - Feb 27
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Great location, clean room and friendly staff!
Reviewed on Dec 14, 2025
Hilton Chicago
Downtown Chicago
Price was ￥341,808, price is now ￥290,271 per person
￥290,271
per person
Feb 22 - Feb 27
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (2,301 reviews)
Room temperature control on th 6th floor was terrible. Way too hot even when turning temp down as low as it would go. Had to open windows to sleep.
In the morning went to grab 2 coffees for over $20 and $80 for parking on top of room. Absolute rip off.
Room was definitely getting dated, pillows, bed and sheets were cheap. Definitely not what I would expectbfrom the Hilton.
On a positive, staff was very nice.
Reviewed on Dec 21, 2025
Don't see what you're looking for?
See all available trips from Tokyo to Historic Route 66
View all trips5* Romantic vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
Price was ￥478,845, price is now ￥375,622 per person
￥375,622
per person
Feb 22 - Feb 27
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Service and clean room - paying attention to the details
Reviewed on Dec 22, 2025
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.
Motel 6 Flagstaff, AZ - West - Woodland Village
Woodlands Village
Price was ￥174,976, price is now ￥170,284 per person
￥170,284
per person
Mar 1 - Mar 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Sedona (SDX)
7.4/10 Good! (1,683 reviews)
The location is great and the motel grounds were clean.
Reviewed on Dec 17, 2025
Getaways at Highlands at Verde Ridge
Verde Santa Fe
Price was ￥181,380, price is now ￥176,890 per person
￥176,890
per person
Mar 1 - Mar 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Sedona (SDX)
9.2/10 Wonderful! (32 reviews)
This place was clean and quiet. Staff were friendly and we enjoyed the amenities. Will definitely go back.
Reviewed on Nov 15, 2025
Best Western Pony Soldier Inn & Suites
Lower Greenlaw Estates
Price was ￥181,306, price is now ￥177,372 per person
￥177,372
per person
Mar 1 - Mar 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Sedona (SDX)
8.4/10 Very Good! (1,006 reviews)
Great room but trains go by constantly at night. It kept my husband and I awake.
Reviewed on Dec 22, 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.
