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.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥259,878, price is now ￥231,756 per person
￥231,756
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Nice hotel, very clean and the buffet breakfast was excellent
Reviewed on Nov 6, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥350,592, price is now ￥290,813 per person
￥290,813
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The Trump International Hotel was absolutely immaculate in appearance and the entire staff were fantastic in all aspects. The location is extremely desirable and within walking distance to numerous restaurants and attractions. However, my suite was somewhat underwhelming in regard to the bathroom. The deep soaking bathtub was smaller in scale than one would expect, and more specifically the shower head is set far too low for those of us who are six feet or taller. I would recommend this property.
Reviewed on Nov 3, 2025
Hilton Chicago O'Hare Airport
O'Hare
Price was ￥372,797, price is now ￥329,660 per person
￥329,660
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
8.2/10 Very Good! (2,141 reviews)
It was okay, nothing terrible, nothing special. The staff was curteous, it waa very convienent.
Reviewed on Oct 31, 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥350,592, price is now ￥290,813 per person
￥290,813
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The Trump International Hotel was absolutely immaculate in appearance and the entire staff were fantastic in all aspects. The location is extremely desirable and within walking distance to numerous restaurants and attractions. However, my suite was somewhat underwhelming in regard to the bathroom. The deep soaking bathtub was smaller in scale than one would expect, and more specifically the shower head is set far too low for those of us who are six feet or taller. I would recommend this property.
Reviewed on Nov 3, 2025
The Peninsula Chicago
Downtown Chicago
Price was ￥1,069,686, price is now ￥950,805 per person
￥950,805
per person
Dec 7 - Dec 13
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,009 reviews)
Room was clean. Staff are always awesome. Our favorite place in Chicago. Thank you
Reviewed on Nov 3, 2025
The Langham, Chicago
Downtown Chicago
Price was ￥983,942, price is now ￥910,020 per person
￥910,020
per person
Dec 7 - Dec 13
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,008 reviews)
Remarkable stay! I will return for my next stay in downtown Chicago. Have stayed at other 5 Star Hotels but this one is now my #1 choice. Thank you to all the staff that made my family's stay a memorable one.
Reviewed on Oct 28, 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.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥259,878, price is now ￥231,756 per person
￥231,756
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Nice hotel, very clean and the buffet breakfast was excellent
Reviewed on Nov 6, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥350,592, price is now ￥290,813 per person
￥290,813
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The Trump International Hotel was absolutely immaculate in appearance and the entire staff were fantastic in all aspects. The location is extremely desirable and within walking distance to numerous restaurants and attractions. However, my suite was somewhat underwhelming in regard to the bathroom. The deep soaking bathtub was smaller in scale than one would expect, and more specifically the shower head is set far too low for those of us who are six feet or taller. I would recommend this property.
Reviewed on Nov 3, 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.
