Title: Winnebago Vacation Packages & Trips 2026 from CA $728 | Expedia.ca [Hotels in Winnebago](https://expedia.ca/Winnebago-Hotels.d3000435733.Travel-Guide-Hotels)[Vacation Rentals in Winnebago](https://expedia.ca/Winnebago-Vacation-Rentals.d3000435733.Travel-Guide-VacationRentals)[Winnebago Car Rentals](https://expedia.ca/Car-Rentals-In-Winnebago.d3000435733.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) # Winnebago 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 Winnebago Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Hilton Grand Vacations Club Chicago Magnificent Mile](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Grand Vacations Club Chicago Magnificent Mile Downtown Chicago CA $728 per person Mar 1 - Mar 4 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Chicago (ORD) 9.2/10 Wonderful! (317 reviews) The room was beautiful and clean and a good city view of the city Reviewed on Nov 26, 2025 ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago CA $1,160 per person Mar 1 - Mar 4 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Excellent service throughout the hotel Reviewed on Nov 29, 2025 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $1,129 per person Mar 1 - Mar 4 found 1 hour ago Roundtrip non-stop flight included Montreal (YMQ) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) All of the above. Staff was wonderful. Room was clean and comfortable. On site amenities were great and food was superb. Best espresso martini I’ve ever tasted. Reviewed on Dec 11, 2025 ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago CA $753 per person Mar 1 - Mar 4 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Very pleasant stay for my birthday! Will definitely come back and recommend to others! Top notch service and rooms were beautiful and comfortable! Reviewed on Dec 13, 2025 ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago CA $806 per person Mar 1 - Mar 4 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Concierge not helpful and neither is was the door man, Neither would get me a cab, they said to just stand outside Reviewed on Dec 4, 2025 ## Ready to book your vacation to Winnebago? Choose your dates ## Winnebago Hotel Deals ![Baymont by Wyndham Rockford](https://images.trvl-media.com/lodging/1000000/80000/75400/75329/abcdff36_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Baymont by Wyndham Rockford 662 N Lyford Rd Rockford IL Fully refundableReserve now, pay when you stay CA $93 CA $105 total Jan 4 - Jan 5, 2026 includes taxes & fees 8.8/10 Excellent! (1,435 reviews) The breakfast variety was amazing and my favorite thing about this hotel. It was very clean and comfortable. Thank you. Reviewed on Dec 11, 2025 [](https://expedia.ca/Hotel-Search?startDate=04%2F01%2F2026&endDate=05%2F01%2F2026&selected=75329&PinnedHotelID=75329&HadPinnedHotel=true®ionId=3000435733) ![Holiday Inn Rockford by IHG](https://images.trvl-media.com/lodging/1000000/30000/27700/27617/2e62a938_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Rockford by IHG 7550 E State Street Rockford IL Fully refundable CA $113 CA $129 total Dec 28 - Dec 29 includes taxes & fees 8.4/10 Very Good! (999 reviews) Shuttle from bus station, clean room, staff was very helpful. Reviewed on Dec 6, 2025 [](https://expedia.ca/Hotel-Search?startDate=28%2F12%2F2025&endDate=29%2F12%2F2025&selected=27617&PinnedHotelID=27617&HadPinnedHotel=true®ionId=3000435733) ![Embassy Suites by Hilton Rockford Riverfront](https://images.trvl-media.com/lodging/40000000/39630000/39624700/39624618/ec2a5a03_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Embassy Suites by Hilton Rockford Riverfront 416 S Main Street Rockford IL Fully refundableReserve now, pay when you stay CA $175 CA $200 total Dec 22 - Dec 23 includes taxes & fees 9.4/10 Exceptional! (878 reviews) Chicago feel 30 minutes from our house. Amazing views on the corner room and staff was great 😁 Reviewed on Dec 7, 2025 [](https://expedia.ca/Hotel-Search?startDate=22%2F12%2F2025&endDate=23%2F12%2F2025&selected=39624618&PinnedHotelID=39624618&HadPinnedHotel=true®ionId=3000435733) [See all 213 properties in Winnebago](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=15%2F12%2F2025&endDate=16%2F12%2F2025®ionId=3000435733) 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