Title: Greenwood Vacation Packages & Trips 2026 from CA $734 | Expedia.ca [Hotels in Greenwood](https://expedia.ca/Greenwood-Hotels.d553248634983419577.Travel-Guide-Hotels)[Vacation Rentals in Greenwood](https://expedia.ca/Greenwood-Vacation-Rentals.d553248634983419577.Travel-Guide-VacationRentals)[Greenwood Car Rentals](https://expedia.ca/Car-Rentals-In-Greenwood.d553248634983419577.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) # Greenwood 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 Greenwood Vacation Take the guesswork out of travel planning with a Greenwood vacation package. A good neighborhood to stay in this captivating city is Powers Lake, which is good for watersports and a lot more. If taking in sights is on the agenda during your trip to Greenwood, visit top attractions like [McHenry County Courthouse](https://www.expedia.ca/McHenry-County-Courthouse-Woodstock.d6187322.Vacation-Attraction), [Petersen Park Beach](https://www.expedia.ca/Petersen-Park-Beach-McHenry.d553248635983991828.Vacation-Attraction) and [Woodstock Opera House](https://www.expedia.ca/Woodstock-Opera-House-Woodstock.d6186936.Vacation-Attraction). Whatever your travel plans or budget, putting together the ultimate tailored Greenwood vacation is a piece of cake with Expedia. ## Top Greenwood 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 $734 per person Mar 26 - Mar 31 found 7 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (347 reviews) Room smelled like food but overall very clean, very great service and staff both night and morning shift. Reviewed on Feb 16, 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 $1,014 per person May 17 - May 21 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Location was perfect! Rooms clean and renovated and breakfast was AMAZING! Staff is really nice and friendly. Would love to stay there again. Reviewed on Feb 23, 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 $793 per person May 17 - May 21 found 1 day ago Roundtrip non-stop 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 ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago CA $1,670 per person Mar 31 - Apr 4 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better. Reviewed on Jan 26, 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 $1,406 per person May 17 - May 21 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Had a great stay!! Kelly at the front desk was so sweet Reviewed on Feb 22, 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_553248634983419577) ## Ready to book your vacation to Greenwood? Choose your dates ## Greenwood Hotel Deals ![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 $138 CA $188 total Feb 25 - Feb 26 includes taxes & fees 8.6/10 Excellent! (1,765 reviews) I would like streaming services readily available especially since spa times aren’t guaranteed. I’d also like options to be available in case a spa service isn’t available at Avani spa. What alternatives are there especially when traveling from another state. It was extremely difficult to reach room ... Reviewed on Feb 23, 2026 [](https://expedia.ca/Hotel-Search?startDate=25%2F02%2F2026&endDate=26%2F02%2F2026&selected=40133&PinnedHotelID=40133&HadPinnedHotel=true®ionId=553248634983419577) ![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 $192 CA $268 total Mar 3 - Mar 4 includes taxes & fees 8.6/10 Excellent! (3,151 reviews) Great facility beautiful areas but the cleanliness of the rooms was horrible drains, showers and the showers heads just nasty. For as much as we paid for one night I was so disappointed with the way the hotel is being maintained especially in the rooms. Reviewed on Feb 23, 2026 [](https://expedia.ca/Hotel-Search?startDate=03%2F03%2F2026&endDate=04%2F03%2F2026&selected=1043867&PinnedHotelID=1043867&HadPinnedHotel=true®ionId=553248634983419577) ![#EnglishPrairieBnB - 8 Bedroom - 4.5 Bathrooms](https://images.trvl-media.com/lodging/68000000/67430000/67422300/67422248/469f0cf9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### #EnglishPrairieBnB - 8 Bedroom - 4.5 Bathrooms Twin Lakes WI 10/10 Exceptional! (44 reviews) Upstairs and basement was not heated good it’s gives discomfort Reviewed on Jan 5, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=10%2F03%2F2026&endDate=11%2F03%2F2026&selected=67422248&PinnedHotelID=67422248&HadPinnedHotel=true®ionId=553248634983419577) [](https://expedia.ca/Hotel-Search?startDate=10%2F03%2F2026&endDate=11%2F03%2F2026&selected=67422248&PinnedHotelID=67422248&HadPinnedHotel=true®ionId=553248634983419577) [See all 1,023 properties in Greenwood](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=25%2F02%2F2026&endDate=26%2F02%2F2026®ionId=553248634983419577) 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