Historic Route 66 Mountain Vacations
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Top Mountain vacation packages 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 18 hours 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 ￥402,709, price is now ￥319,210 per person
￥319,210
per person
Mar 14 - Mar 18
found 24 hours 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
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 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
The staff was incredible and the room was spotless.
Reviewed on Jan 25, 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 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
Beautiful hotel, stunning views, excellent location, amazing staff, and phenomenal rooftop!
Reviewed on Jan 26, 2026
The Emily Hotel
Downtown Chicago
Price was ￥319,223, price is now ￥277,370 per person
￥277,370
per person
Mar 14 - Mar 18
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Hotel was very stylish…hotel bar and food was great too. Staff was courteous and rooms were clean, we will stay here again.
Reviewed on Jan 25, 2026
Don't see what you're looking for?
See all available trips from Osaka to Historic Route 66
View all trips5* Mountain 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 18 hours 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 ￥402,709, price is now ￥319,210 per person
￥319,210
per person
Mar 14 - Mar 18
found 24 hours 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 Mountain 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 18 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
The staff was incredible and the room was spotless.
Reviewed on Jan 25, 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 18 hours 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 17 hours 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 Mountain 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 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
The staff was incredible and the room was spotless.
Reviewed on Jan 25, 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 24 hours 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 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
Beautiful hotel, stunning views, excellent location, amazing staff, and phenomenal rooftop!
Reviewed on Jan 26, 2026
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.
