Great River Road Luxury Vacations
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Top Luxury vacation packages in Great River Road
Price found within the past 48 hours. Click for updated prices.
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥451,858, price is now ￥346,480 per person
￥346,480
per person
May 1 - May 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) 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
Level Chicago Fulton Market
Downtown Chicago
Price was ￥348,173, price is now ￥270,984 per person
￥270,984
per person
May 1 - May 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Hot tub wasn’t working(freezing cold) and no robes in my room. Need bigger roller carts and cheaper or free parking. Other than that the room, view, amenities were excellent.
Reviewed on Feb 9, 2026
Hilton Chicago O'Hare Airport
O'Hare
Price was ￥308,092, price is now ￥255,944 per person
￥255,944
per person
May 1 - May 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Food at sports bar was great along with the service.
Bedding was top notch, room clean& nice TV
Reviewed on Feb 9, 2026
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See all available trips from Tokyo to Great River Road
View all trips5* Luxury vacations in Great River Road
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥380,704, price is now ￥326,720 per person
￥326,720
per person
May 2 - May 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥451,858, price is now ￥346,480 per person
￥346,480
per person
May 1 - May 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) 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
Don't see what you're looking for?
See all available trips from Tokyo to Great River Road
View all trips3 Night Luxury vacations in Great River Road
Price found within the past 48 hours. Click for updated prices.
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥392,486, price is now ￥317,936 per person
￥317,936
per person
May 2 - May 5
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) 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
Level Chicago – Old Town
Downtown Chicago
Price was ￥323,898, price is now ￥277,932 per person
￥277,932
per person
May 2 - May 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!
Reviewed on Feb 2, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Great River Road
View all trips4 Night Luxury vacations in Great River Road
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
Price was ￥348,173, price is now ￥270,984 per person
￥270,984
per person
May 1 - May 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Hot tub wasn’t working(freezing cold) and no robes in my room. Need bigger roller carts and cheaper or free parking. Other than that the room, view, amenities were excellent.
Reviewed on Feb 9, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥451,858, price is now ￥346,480 per person
￥346,480
per person
May 1 - May 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) 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
Don't see what you're looking for?
See all available trips from Tokyo to Great River Road
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
