Winslow Holidays
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Top Flight + Hotel Deals in Winslow
Price found within the past 48 hours. Click for updated prices.
Hilton Chicago O'Hare Airport
O'Hare
Price was €1,332, price is now €1,065 per person
€1,065
per person
11 Apr - 16 Apr
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.4/10 Very Good! (2,217 reviews)
Had a steak and ribs at the restaurant downstairs and both were delicious
Reviewed on 1 Mar 2026
Hyatt Centric The Loop Chicago
Downtown Chicago
Price was €1,193, price is now €1,012 per person
€1,012
per person
11 Apr - 16 Apr
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (2,385 reviews)
One of my fav hotels in Chicago! The staff helpful and friendly. I’ll see them again soon!
Reviewed on 8 Mar 2026
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was €1,066, price is now €904 per person
€904
per person
11 Apr - 16 Apr
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,014 reviews)
Center of the Loop, easy walk to a majority of landmark sights.
Reviewed on 5 Mar 2026
Top hotels in Winslow
Country Inn & Suites by Radisson, Freeport, IL
1710 South Dirck Drive Freeport IL
Fully refundable
The price is €100 per night from 15 Mar to 16 Mar
€100
15 Mar - 16 Mar
includes taxes & fees
9/10 Wonderful! (869 reviews)
Clean rooms, comfortable bed, good breakfast on the morning. Great location with plenty of dining options close by.
Reviewed on 2 Mar 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 €71 per night from 15 Mar to 16 Mar
€71
15 Mar - 16 Mar
includes taxes & fees
9/10 Wonderful! (836 reviews)
Clean rooms, friendly staff, nice location
Reviewed on 8 Mar 2026
Amazing Log Cabin with Beautiful Views at Apple Canyon Lake
Apple River IL
9.8/10 Exceptional! (226 reviews)
Cabin was beautiful and the perfect getaway for our family ski trip at Chestnut Mountain. Comfortable beds and linens, hosts were very hospitable, and kitchen was well-stocked.
Reviewed on 15 Feb 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.
