Title: Woodstock Vacation Packages & Trips 2026 from CA $857 | Expedia.ca [Hotels in Woodstock](https://expedia.ca/Woodstock-Hotels.d7936.Travel-Guide-Hotels)[Vacation Rentals in Woodstock](https://expedia.ca/Woodstock-Vacation-Rentals.d7936.Travel-Guide-VacationRentals)[Flights to Woodstock](https://expedia.ca/Cheap-Flights-To-Woodstock.d7936.Travel-Guide-Flights)[Woodstock Car Rentals](https://expedia.ca/Car-Rentals-In-Woodstock.d7936.Car-Rental-Guide) ![](https://images.trvl-media.com/place/7936/5032a45c-3811-43f0-8ba7-edf1f80b19af.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Woodstock Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings #### Your Woodstock Vacation With one of our vacation packages to Woodstock, you'll discover infinite opportunities for excitement and adventure. There's tons to experience, including its rich history and spectacular views. You'll want to do some exploring during your trip to Woodstock. Make time for top attractions such as [McHenry County College](https://www.expedia.ca/McHenry-County-College-Illinois.d6183854.Vacation-Attraction), [McHenry County Courthouse](https://www.expedia.ca/McHenry-County-Courthouse-Woodstock.d6187322.Vacation-Attraction) and [Woodstock Opera House](https://www.expedia.ca/Woodstock-Opera-House-Woodstock.d6186936.Vacation-Attraction). No matter your travel plans or the size of your budget, putting together the ultimate tailored Woodstock vacation is easy with Expedia. ## Top Woodstock 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 $857 per person Apr 30 - May 3 found 1 day ago Roundtrip 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 ![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 $1,005 per person Mar 13 - Mar 16 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 ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago CA $954 per person Mar 15 - Mar 19 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (380 reviews) My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone! Reviewed on Feb 2, 2026 ![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 $1,140 per person Apr 16 - Apr 21 found 16 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Amazing hotel. Always stay here when I make a trip to Chicago. Reviewed on Feb 10, 2026 ![Hyatt Centric Chicago Magnificent Mile](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/w3837h2249x3y0-2724cf53_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Centric Chicago Magnificent Mile Downtown Chicago CA $1,085 per person Apr 16 - Apr 21 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,034 reviews) All good. bar staff was not that friendlly Reviewed on Feb 3, 2026 ## Ready to book your vacation to Woodstock? Choose your dates ## Woodstock Hotel Deals ![AmericInn by Wyndham Woodstock IL](https://images.trvl-media.com/lodging/1000000/30000/20700/20685/18ff1b13_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### AmericInn by Wyndham Woodstock IL 990 Lake Avenue Woodstock IL Fully refundableReserve now, pay when you stay CA $110 CA $122 total Feb 18 - Feb 19 includes taxes & fees 7.8/10 Good! (1,003 reviews) I forgot my weighted pillow that is highly sentimental. We called and inquired about it. They promptly called back and are mailing it back to me. They were kind and compassionate!! Reviewed on Feb 5, 2026 [](https://expedia.ca/Hotel-Search?startDate=18%2F02%2F2026&endDate=19%2F02%2F2026&selected=20685&PinnedHotelID=20685&HadPinnedHotel=true®ionId=7936) ![Abbey Resort and Avani Spa](https://images.trvl-media.com/lodging/1000000/50000/40200/40133/938090f1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Abbey Resort and Avani Spa 269 Fontana Boulevard Fontana WI Fully refundableReserve now, pay when you stay CA $133 CA $182 total Feb 18 - Feb 19 includes taxes & fees 8.4/10 Very Good! (1,734 reviews) It was a nice hotel with a great spa and workout facilities. Bed was comfy and location was perfect. Reviewed on Feb 9, 2026 [](https://expedia.ca/Hotel-Search?startDate=18%2F02%2F2026&endDate=19%2F02%2F2026&selected=40133&PinnedHotelID=40133&HadPinnedHotel=true®ionId=7936) ![Timber Ridge Lodge and Waterpark](https://images.trvl-media.com/lodging/2000000/1050000/1043900/1043867/6d6345d6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Timber Ridge Lodge and Waterpark 7020 Grand Geneva Way Lake Geneva WI Fully refundableReserve now, pay when you stay CA $191 CA $265 total Feb 26 - Feb 27 includes taxes & fees 8.6/10 Excellent! (3,130 reviews) Great stay. First family trip with my little girl who is 2yr old and she loved here water park, whirlpool bath! We will come back again ;) btw staffs are so nice👍 Reviewed on Feb 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=26%2F02%2F2026&endDate=27%2F02%2F2026&selected=1043867&PinnedHotelID=1043867&HadPinnedHotel=true®ionId=7936) [See all 1,154 properties in Woodstock](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=12%2F02%2F2026&endDate=13%2F02%2F2026®ionId=7936) 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