Winslow Vacations from ￥196,404
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The Latest Winslow Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥363,190, price is now ￥274,446 per person
￥274,446
per person
Mar 24 - Mar 28
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!
Reviewed on Jan 3, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥266,548, price is now ￥215,022 per person
￥215,022
per person
Mar 24 - Mar 28
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Great breakfast, Clean room, enjoyed the stay
Reviewed on Jan 9, 2026
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ￥271,462, price is now ￥219,834 per person
￥219,834
per person
Mar 24 - Mar 28
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Perfect location, comfortable and clean room
Reviewed on Jan 5, 2026
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was ￥293,750, price is now ￥241,002 per person
￥241,002
per person
Mar 24 - Mar 28
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.
Reviewed on Dec 18, 2025
Find the Best Winslow Vacation Packages
Winslow Hotel Deals
Country Inn & Suites by Radisson, Freeport, IL
1710 South Dirck Drive Freeport IL
Fully refundable
The price is ￥16,484 per night from Feb 7 to Feb 8
￥16,484
￥18,295 total
Feb 7 - Feb 8
includes taxes & fees
8.8/10 Excellent! (853 reviews)
Safe, clean & convenient.
Reviewed on Jan 3, 2026
Super 8 by Wyndham Monroe WI
500 6th St and Hwy 69 Monroe WI
Fully refundableReserve now, pay when you stay
The price is ￥12,403 per night from Jan 22 to Jan 23
￥12,403
￥13,581 total
Jan 22 - Jan 23
includes taxes & fees
8.8/10 Excellent! (824 reviews)
This hotel did not have an elevator. I don't remember ever staying at a hotel that does not have an elevator. Our room was on the second floor. We had a lot of luggage and dresses/ suits that needed to be carried up (and down) steps in order to get to our room on the second floor. An elevator would ...
Reviewed on Jan 5, 2026
Baymont by Wyndham Freeport
1060 Riverside Dr Freeport IL
Fully refundableReserve now, pay when you stay
The price is ￥12,004 per night from Jan 19 to Jan 20
￥12,004
￥13,322 total
Jan 19 - Jan 20
includes taxes & fees
7.8/10 Good! (714 reviews)
Front desk staff was awesome, very professional, courteous and friendly, room was very clean bed was very comfortable
Reviewed on Jan 1, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
