Historic Route 66 All inclusive Vacations
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Top All inclusive 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 ￥282,092, price is now ￥223,838 per person
￥223,838
per person
Mar 24 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Great breakfast buffet, incredible staff, very clean, close to everything we wanted to do! 10/10 and will certainly stay here again!
Reviewed on Jan 26, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥403,668, price is now ￥297,720 per person
￥297,720
per person
Mar 24 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on Jan 24, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥299,862, price is now ￥244,036 per person
￥244,036
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) 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
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See all available trips from Tokyo to Historic Route 66
View all trips5* All inclusive vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥299,862, price is now ￥244,036 per person
￥244,036
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) 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
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥403,668, price is now ￥297,720 per person
￥297,720
per person
Mar 24 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on Jan 24, 2026
Don't see what you're looking for?
See all available trips from Osaka to Historic Route 66
View all trips3 Night All inclusive vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥225,194, price is now ￥183,198 per person
￥183,198
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Great breakfast buffet, incredible staff, very clean, close to everything we wanted to do! 10/10 and will certainly stay here again!
Reviewed on Jan 26, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥299,862, price is now ￥244,036 per person
￥244,036
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) 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
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥285,612, price is now ￥233,135 per person
￥233,135
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on Jan 24, 2026
Don't see what you're looking for?
See all available trips from Osaka to Historic Route 66
View all trips4 Night All inclusive vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥340,920, price is now ￥274,182 per person
￥274,182
per person
Mar 14 - Mar 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Great breakfast buffet, incredible staff, very clean, close to everything we wanted to do! 10/10 and will certainly stay here again!
Reviewed on Jan 26, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥402,709, price is now ￥319,210 per person
￥319,210
per person
Mar 14 - Mar 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on Jan 24, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥345,598, price is now ￥295,217 per person
￥295,217
per person
Mar 14 - Mar 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
Staff was kind and it was at a great location!
Reviewed on Jan 27, 2026
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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.
