Winslow Holidays
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Top Flight + Hotel Deals in Winslow
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was €811, price is now €533 per person
€533
per person
8 Jun - 11 Jun
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.2/10 Very Good! (2,636 reviews)
Very nice place and staff, breakfast very well prepared and served
Reviewed on 23 Apr 2026
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Save 100% on your flight
Price was €1,015, price is now €651 per person
€651
per person
8 Jun - 11 Jun
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (2,500 reviews)
Great location and very nice Hotel. Would stay there again!
Reviewed on 21 Apr 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Save 100% on your flight
Price was €921, price is now €628 per person
€628
per person
8 Jun - 11 Jun
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (1,417 reviews)
Great location and converted old Virgin Hotel. Room was fine and hotel basics were fine. There wasn’t any room service daily or for my 3 night stay. There was a strike for housekeepers and they were LOUD out front everyday. Not sure what the hotel fee was for on top of Expedia hotel charge was for, they gave me 2 waters the first day and that was it. They also upsell their vacation club/time share a lot, kinda odd.
Reviewed on 14 Apr 2026
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Save 100% on your flight
Price was €866, price is now €613 per person
€613
per person
8 Jun - 11 Jun
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.4/10 Exceptional! (1,047 reviews)
This property is in a great location. The staff were friendly and the room was clean. The room we were in was very small and used. The building is really cool but we were super disappointed with it being under construction with no place to hang out and have a drink. We weren’t notified of the construction until right before our stay. We would have chosen somewhere else because of this.
Reviewed on 21 Apr 2026
Top hotels in Winslow
Country Inn & Suites by Radisson, Freeport, IL
1710 South Dirck Drive Freeport IL
Fully refundable
The price is €111 per night from 10 May to 11 May
€111
10 May - 11 May
includes taxes & fees
9/10 Wonderful! (882 reviews)
cleaning room was perfect. staff was too breakfast good
Reviewed on 20 Apr 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 €76 per night from 24 May to 25 May
€76
24 May - 25 May
includes taxes & fees
9/10 Wonderful! (849 reviews)
From my arrival to my leaving Everyone was Very Professional and Caring. Very Helpful and my room was so comfortable. Its an older hotel but I felt very welcome, safe and the hot breakfast was a very well maintained. I really enjoyed my stay.
Reviewed on 23 Apr 2026
Country Inn & Suites by Radisson, Stockton, IL
200 Dillon Ave Stockton IL
The price is €87 per night from 14 May to 15 May
€87
14 May - 15 May
includes taxes & fees
8.4/10 Very Good! (661 reviews)
Clean, affordable, and rooms that exceeded my expectations for the price.
Reviewed on 23 Apr 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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