Title: Winslow Vacation Packages & Trips 2026 from CA $701 | Expedia.ca [Hotels in Winslow](https://expedia.ca/Winslow-Hotels.d553248634983150076.Travel-Guide-Hotels)[Vacation Rentals in Winslow](https://expedia.ca/Winslow-Vacation-Rentals.d553248634983150076.Travel-Guide-VacationRentals)[Winslow Car Rentals](https://expedia.ca/Car-Rentals-In-Winslow.d553248634983150076.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Winslow Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place #### Your Winslow Vacation Memorable adventures await when you reserve a vacation package to Winslow. Whether you're a foodie, history buff or just a traveler who loves to discover new places, there's something for everyone in this awesome city. Any trip to Winslow has to include a little sightseeing. [Lake Le Aqua Na State Park](https://www.expedia.ca/Lake-Le-Aqua-Na-State-Park-Illinois.d6310752.Vacation-Attraction) is a great place to begin exploring. Stop daydreaming and start traveling. Check out the range of options on Expedia today and put your Winslow vacation plans into motion! ## Top Winslow Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/b2962364_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $701 per person Apr 17 - Apr 21 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (347 reviews) Hot tub wasn’t working(freezing cold) and no robes in my room. Need bigger roller carts and cheaper or free parking. Other than that the room, view, amenities were excellent. Reviewed on Feb 9, 2026 ![La Banque Hotel](https://images.trvl-media.com/lodging/15000000/14710000/14702200/14702161/a8c9af9e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### La Banque Hotel CA $888 per person Apr 14 - Apr 19 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 9.4/10 Exceptional! (447 reviews) Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring. Reviewed on Jan 26, 2026 ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago CA $1,033 per person Apr 16 - Apr 21 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Friendly staff, tasteful room Reviewed on Feb 11, 2026 ![Aloft Chicago Downtown River North](https://images.trvl-media.com/lodging/6000000/5470000/5461400/5461400/w4000h2662x0y0-8993d93f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Aloft Chicago Downtown River North Downtown Chicago CA $872 per person Apr 16 - Apr 21 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,159 reviews) Staff was great but next to fire station. Beware very noisy if staying city view Reviewed on Feb 8, 2026 ![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/668d065a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago - River North Downtown Chicago CA $837 per person Apr 16 - Apr 21 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (766 reviews) Great stay. Would come again. Reviewed on Jan 19, 2026 ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_553248634983150076) ## Ready to book your vacation to Winslow? Choose your dates ## Winslow Hotel Deals ![Super 8 by Wyndham Monroe WI](https://images.trvl-media.com/lodging/1000000/460000/459900/459802/b2846b8b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Super 8 by Wyndham Monroe WI 500 6th St and Hwy 69 Monroe WI Fully refundableReserve now, pay when you stay CA $94 CA $103 total Mar 1 - Mar 2 includes taxes & fees [](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=459802&PinnedHotelID=459802&HadPinnedHotel=true®ionId=553248634983150076) ![Country Inn & Suites by Radisson, Freeport, IL](https://images.trvl-media.com/lodging/1000000/30000/28000/27974/9cdfac50_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Country Inn & Suites by Radisson, Freeport, IL 1710 South Dirck Drive Freeport IL Fully refundable CA $132 CA $146 total Mar 1 - Mar 2 includes taxes & fees 9/10 Wonderful! (863 reviews) The staff was great and Patrice who ran the breakfast area was wonderful but the carpet in our room had stains and there were ants by the hot tub and bugs by the pool. Reviewed on Feb 10, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=27974&PinnedHotelID=27974&HadPinnedHotel=true®ionId=553248634983150076) ![Hampton Inn Freeport](https://images.trvl-media.com/lodging/2000000/1640000/1632400/1632362/3a80a350_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn Freeport 109 S Galena Ave Freeport IL Fully refundableReserve now, pay when you stay CA $138 CA $153 total Feb 22 - Feb 23 includes taxes & fees 8.8/10 Excellent! (456 reviews) The room was spotless and the beds were comfortable. The only issue we had which was out of the hotels control was the noise from the cars passing by at night . The staff was polite and courtesy and the food was delicious . The pool was warm and clean Reviewed on Feb 8, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=1632362&PinnedHotelID=1632362&HadPinnedHotel=true®ionId=553248634983150076) [See all 102 properties in Winslow](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=13%2F02%2F2026&endDate=14%2F02%2F2026®ionId=553248634983150076) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app