Historic Route 66 Beach Vacations
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Top Beach vacation packages in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥275,472, price is now ￥233,604 per person
￥233,604
per person
Apr 8 - Apr 13
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
I liked the hotel. The staff was very courteous and friendly. The room was cute. The location is fantastic.
Reviewed on Jan 20, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥334,890, price is now ￥251,553 per person
￥251,553
per person
Apr 8 - Apr 13
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
No parking available, the hotel was nice, room etc. but breakfast was overly crowded, cafeteria style. They say breakfast is free with stay but then I was charged $85. When I asked what the charge was for they said for breakfast, room service etc. plus parking was an additional $150, not on site so not too pleased with the overall experience. Staff was very nice though.
Reviewed on Jan 22, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥451,724, price is now ￥343,696 per person
￥343,696
per person
Mar 18 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Exceptional service, great location, beautiful hotel
Reviewed on Jan 20, 2026
The Emily Hotel
Downtown Chicago
Price was ￥341,857, price is now ￥281,974 per person
￥281,974
per person
Mar 18 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Everything about this hotel is special. Great staff- awesome restaurant/bar. Location is perfect. This hotel is my destination every time I come to the city. Which is quite often.
Reviewed on Jan 20, 2026
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View all trips5* Beach 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 ￥451,724, price is now ￥343,696 per person
￥343,696
per person
Mar 18 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Exceptional service, great location, beautiful hotel
Reviewed on Jan 20, 2026
Nobu Hotel Chicago
Downtown Chicago
Price was ￥402,703, price is now ￥369,156 per person
￥369,156
per person
Mar 18 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (748 reviews)
Room was great and spacious. Service was great. The pool and sauna were nice also.
Reviewed on Jan 13, 2026
The Ritz-Carlton, Chicago
Downtown Chicago
Price was ￥385,644, price is now ￥385,644 per person
￥385,644
per person
Mar 18 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
Amazing experience the place was amazing. The people were fantastic. The food was incredible. I pray I can do it again.
Reviewed on Jan 13, 2026
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View all trips4 Night Beach vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hilton Orrington / Evanston
Downtown Evanston
Price was ￥274,210, price is now ￥246,694 per person
￥246,694
per person
Mar 17 - Mar 21
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
7.6/10 Good! (1,002 reviews)
I would stay here again if I need to stay in Evanston again. Thanks
Reviewed on Jan 19, 2026
Hilton Chicago O'Hare Airport
O'Hare
Price was ￥328,756, price is now ￥293,110 per person
￥293,110
per person
Mar 17 - Mar 21
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Hotel was very clean. Concierge was great with advice. Sports bar pepperoni pizza was great and the french fries were just as freshly cooked. Room was clean. Bed was great. Shower pressure great. Toilet correct height for a man of my age. Pillows…..pillows with a firmness of that of a 48 year old mother who breast fed all her 7 children until 9 months old. Glad the kids are good but those pillows need work Hilton. God Bless and safe travels to all. See you next time.
Reviewed on Jan 20, 2026
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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.
