Title: Winthrop Harbor Vacation Packages & Trips 2026 from CA $707 | Expedia.ca [Hotels in Winthrop Harbor](https://expedia.ca/Winthrop-Harbor-Hotels.d183192.Travel-Guide-Hotels)[Vacation Rentals in Winthrop Harbor](https://expedia.ca/Winthrop-Harbor-Vacation-Rentals.d183192.Travel-Guide-VacationRentals)[Winthrop Harbor Car Rentals](https://expedia.ca/Car-Rentals-In-Winthrop-Harbor.d183192.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6338716/94ae8062-01b7-4cdf-b3dd-7ea1c75a7654.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Winthrop Harbor 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 ## Top Winthrop Harbor Vacation Deals Price found within the past 48 hours. Click for updated prices. ![JW Marriott Chicago](https://images.trvl-media.com/lodging/4000000/3540000/3538400/3538327/232aa080_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### JW Marriott Chicago Downtown Chicago CA $707 per person May 1 - May 3 found 12 hours ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.2/10 Wonderful! (1,000 reviews) Bottle of waters were not stocked in the refrigerator. Reviewed on Jan 6, 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 $743 per person Apr 9 - Apr 12 found 1 day ago Roundtrip flight included Toronto (YTO) 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 $828 per person Apr 17 - Apr 20 found 1 day ago Roundtrip flight included Montreal Metropolitan Airport (YHU) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Everything was amazing, specially the breakfast buffet. Reviewed on Feb 7, 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 $708 per person Apr 17 - Apr 20 found 1 day ago Roundtrip flight included Montreal Metropolitan Airport (YHU) to Chicago (ORD) 9/10 Wonderful! (766 reviews) Great stay. Would come again. Reviewed on Jan 19, 2026 ![Holiday Inn Club Vacations at Lake Geneva Resort by IHG](https://images.trvl-media.com/lodging/2000000/1690000/1681300/1681285/bf062b0f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Club Vacations at Lake Geneva Resort by IHG CA $723 per person Apr 21 - Apr 25 found 17 hours ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 8.8/10 Excellent! (1,003 reviews) My room was very clean, which I appreciated. We booked a suite, but the first one opened directly into the bedroom, and being on the first floor, I didn’t feel comfortable with that layout. I requested a room change, and the staff handled it quickly and professionally, which I really appreciated. One thing that was a bit confusing was the inconsistency between suites—some had a full kitchen while others only had a range top. It would be helpful to know that in advance when booking. Overall, the stay was quiet and peaceful during the week, which was exactly what we wanted. When we arrived on Saturday afternoon, the atmosphere was completely different—lots of people, plenty of activity, and a lively environment. The only real downside was that the room felt drafty. We ended up putting a towel under the door to help block the cold air. Aside from those small issues, it was a comfortable stay with a good stay. Reviewed on Jan 16, 2026 ## Ready to book your vacation to Winthrop Harbor? Choose your dates ## Winthrop Harbor Hotel Deals ![Motel Sun Inn](https://images.trvl-media.com/lodging/2000000/1280000/1279900/1279846/93033a15_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Motel Sun Inn 301 Sheridan Road Winthrop Harbor IL Fully refundableReserve now, pay when you stay 6.8/10 (276 reviews) I have stayed here several times in the last year and a half. The room is very clean! Staff is very kind and helpful! Good rate! Thank you again for everything! Reviewed on Nov 11, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=1279846&PinnedHotelID=1279846&HadPinnedHotel=true®ionId=183192) [](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=1279846&PinnedHotelID=1279846&HadPinnedHotel=true®ionId=183192) ![La Quinta Inn & Suites by Wyndham Chicago Gurnee](https://images.trvl-media.com/lodging/1000000/60000/50200/50124/52a8ce1f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### La Quinta Inn & Suites by Wyndham Chicago Gurnee 5688 Northridge Rd Gurnee IL Fully refundableReserve now, pay when you stay CA $86 CA $96 total Mar 1 - Mar 2 includes taxes & fees 7.8/10 Good! (1,499 reviews) Great breakfast , super helpful staff, nice rooms Reviewed on Feb 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=50124&PinnedHotelID=50124&HadPinnedHotel=true®ionId=183192) ![Wingate by Wyndham Gurnee](https://images.trvl-media.com/lodging/1000000/10000/4800/4715/51b2dfd0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Wingate by Wyndham Gurnee 6090 Gurnee Mills Blvd E Gurnee IL Fully refundableReserve now, pay when you stay CA $105 CA $117 total Feb 8 - Feb 9 includes taxes & fees 8.8/10 Excellent! (1,003 reviews) Friendly and helpful staff. Everything about this hotel was clean. I was particularly impressed with Joe they continued to clean the breakfast area. Our room was large and comfortable. Very clean. We stayed for a long weekend. Will stay here sign in our next trip up. Reviewed on Feb 2, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F02%2F2026&endDate=09%2F02%2F2026&selected=4715&PinnedHotelID=4715&HadPinnedHotel=true®ionId=183192) [See all 671 properties in Winthrop Harbor](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F02%2F2026&endDate=09%2F02%2F2026®ionId=183192) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. 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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