Winslow Vacations from ₩542,004
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₩234,741 when you book a flight and hotel together*
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The Latest Winslow Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ₩712,078, price is now ₩561,386 per person
₩561,386
per person
Dec 23 - Dec 25
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Nice hotel, very clean and the buffet breakfast was excellent
Reviewed on Nov 6, 2025
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ₩671,293, price is now ₩553,502 per person
₩553,502
per person
Dec 23 - Dec 25
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
A+++ in all areas.
And fabulous location.
Reviewed on Nov 6, 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 ₩166,404 per night from Nov 19 to Nov 20
₩166,404
₩184,675 total
Nov 19 - Nov 20
includes taxes & fees
8.8/10 Excellent! (838 reviews)
Nice staff, clean rooms, good breakfast
Reviewed on Nov 2, 2025
Baymont by Wyndham Freeport
1060 Riverside Dr, Freeport, IL
Fully refundableReserve now, pay when you stay
The price is ₩112,782 per night from Nov 13 to Nov 14
₩112,782
₩125,165 total
Nov 13 - Nov 14
includes taxes & fees
7.8/10 Good! (701 reviews)
Had i not made my reservation ahead of time and saw the condition of the carpets first, I probably would have not checked in. If our room wasn't clean when we opened the room door, i would have left. It appears the hall/stair carpets have never been cleaned and/or vacuumed rarely. My first impression ...
Reviewed on Nov 1, 2025
Super 8 by Wyndham Monroe WI
500 6th St and Hwy 69, Monroe, WI
Fully refundableReserve now, pay when you stay
The price is ₩107,879 per night from Dec 8 to Dec 9
₩107,879
₩118,127 total
Dec 8 - Dec 9
includes taxes & fees
8.8/10 Excellent! (794 reviews)
Location convenient- walking distance to restaurants and grocery store. Staff polite & professional Wish there was in room coffee- in the past there was a small coffee pot in the room.
Reviewed on Oct 30, 2025
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.
