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.
Swissotel - Chicago
Downtown Chicago
Price was ￥519,392, price is now ￥369,706 per person
￥369,706
per person
Jul 19 - Jul 26
just found
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9/10 Wonderful! (3,332 reviews)
Excellent location, walk to all major attractions. Friendly staff. Hotel room was very clean and comfortable. Price was pretty reasonable
Reviewed on May 26, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥562,066, price is now ￥391,626 per person
￥391,626
per person
Jul 19 - Jul 26
just found
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (4,188 reviews)
This hotel is amazing, Great location, super clean and stuff was kind, informative and very respectful! The breakfast was well organized considering the amount people served! Not a missing items at any moment!
The rooftop bar was very pleasant place to sit and chill.
Strongly recommended!!!
Reviewed on May 26, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥559,075, price is now ￥414,126 per person
￥414,126
per person
Jul 19 - Jul 26
just found
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (2,507 reviews)
Great views of the lake, staff very helpful the rooms were clean and comfortable. Would stay there again!
Reviewed on May 26, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥544,490, price is now ￥410,328 per person
￥410,328
per person
Jul 19 - Jul 26
just found
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (3,727 reviews)
Excellent location! Great views from our room.
Reviewed on May 25, 2026
Viceroy Chicago
Downtown Chicago
Price was ￥627,481, price is now ￥487,556 per person
￥487,556
per person
Jul 30 - Aug 5
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,231 reviews)
I don’t think I have ever encountered a more polite, charming, and informed staff. As someone who has worked in the service industry I assume that your training program does an excellent job. The hotel is beautiful and well maintained. We’ll be back.
Reviewed on May 25, 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 ￥699,977, price is now ￥527,073 per person
￥527,073
per person
Jul 30 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,872 reviews)
Location, cleanliness, overall staff assistance and service and of course breakfast
Reviewed on May 26, 2026
Rosewood Inn of the Anasazi
Downtown Santa Fe
Price was ￥986,702, price is now ￥857,552 per person
￥857,552
per person
Aug 8 - Aug 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Albuquerque (ABQ)
9.6/10 Exceptional! (897 reviews)
Beautiful hotel right near everything in Santa Fe. We barely needed our car which was great.
Reviewed on Apr 24, 2026
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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.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥356,926, price is now ￥291,502 per person
￥291,502
per person
Aug 3 - Aug 6
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,188 reviews)
This hotel is amazing, Great location, super clean and stuff was kind, informative and very respectful! The breakfast was well organized considering the amount people served! Not a missing items at any moment!
The rooftop bar was very pleasant place to sit and chill.
Strongly recommended!!!
Reviewed on May 26, 2026
Swissotel - Chicago
Downtown Chicago
Price was ￥374,152, price is now ￥302,189 per person
￥302,189
per person
Aug 3 - Aug 6
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,332 reviews)
Excellent location, walk to all major attractions. Friendly staff. Hotel room was very clean and comfortable. Price was pretty reasonable
Reviewed on May 26, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥449,300, price is now ￥369,966 per person
￥369,966
per person
Aug 2 - Aug 5
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,872 reviews)
Location, cleanliness, overall staff assistance and service and of course breakfast
Reviewed on May 26, 2026
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View all trips4 Night Romantic vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Duets Bed & Breakfast
Pearl District
Price was ￥471,496, price is now ￥431,428 per person
￥431,428
per person
Aug 6 - Aug 10
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Tulsa (TUL)
10/10 Exceptional! (11 reviews)
Duets was the PERFECT stay for my wife and I on our wedding night. The location is perfect and the room was AMAZING. Even if you’re from Tulsa, consider this a little staycation due to the Leon Russell memorabilia and location. 10/10 we will be back!!
Reviewed on Oct 26, 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.
