Title: Sleepy Hollow Vacation Packages & Trips 2025/2026 from CA $493 | Expedia.ca [Hotels in Sleepy Hollow](https://expedia.ca/Sleepy-Hollow-Hotels.d3000435324.Travel-Guide-Hotels)[Vacation Rentals in Sleepy Hollow](https://expedia.ca/Sleepy-Hollow-Vacation-Rentals.d3000435324.Travel-Guide-VacationRentals)[Sleepy Hollow Car Rentals](https://expedia.ca/Car-Rentals-In-Sleepy-Hollow.d3000435324.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) # Sleepy Hollow 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 Sleepy Hollow Vacation Entertainment, history, art and more … There's so much to experience with a Sleepy Hollow vacation package. And with the ability to customize your city getaway, it's guaranteed to be one you won't forget. Make your trip to Sleepy Hollow even more fun by going sightseeing. [Grand Victoria Casino](https://www.expedia.ca/Grand-Victoria-Casino-Elgin.d6065129.Vacation-Attraction), [Santas Village](https://www.expedia.ca/Santas-Village-East-Dundee.d553248621532658557.Vacation-Attraction) and [NOW Arena](https://www.expedia.ca/NOW-Arena-Chicago.d6192396.Vacation-Attraction) are among the top attractions worth exploring. Whatever your travel plans or budget, organizing your ultimate tailored Sleepy Hollow vacation is simple with Expedia. ## Top Sleepy Hollow 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 $493 per person Nov 24 - Nov 26 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (291 reviews) Food price was high but everything was fine Reviewed on Oct 4, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-24/2025-11-26/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=1qy9L2f9MnB3Zlaf3cNbvvsjFfCb23ZyJ803se0v0hA6ln_BXbMxGrfFxGKI4pGM) ![The Westin Michigan Avenue Chicago](https://images.trvl-media.com/lodging/1000000/30000/21100/21055/dcfbf36b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Michigan Avenue Chicago Downtown Chicago CA $1,012 per person Dec 24 - Dec 29 found 23 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 8.8/10 Excellent! (1,046 reviews) One bad part -drain in tub very slow. Called to fix it but even afterwards still slow. Also room was not cleaned one day, had to call to get it done. Reviewed on Oct 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-24/2025-12-29/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=21055&paandie=true&dealMarker=6CuNs0vxu2uILjtBFDt_O5Di8y6ylf3_EUc7MwsMNOmXgQ4l_lb_v2dVtFwugTVb) ![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 $1,258 per person Dec 15 - Dec 19 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) The best hotel in chicago Reviewed on Oct 11, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-15/2025-12-19/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=q82CN2n13NUTAYSDQ7OVElA2zRqpnpMcVegRZ0dTijppc3v143BvehMKo750T2K8) ![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 $707 per person Dec 15 - Dec 19 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) I loved the hotel, however I would request an inside room next time. It was extremely noisy outside. Reviewed on Oct 11, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-15/2025-12-19/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=q82CN2n13NUTAYSDQ7OVErASIb-oyoMeuDelX2KXuZhiRuJWTN1hqOCUL2zNx8O1) ![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 $1,565 per person Dec 15 - Dec 19 found 19 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.4/10 Exceptional! (1,002 reviews) Simply love this hotel Reviewed on Sep 18, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-15/2025-12-19/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2717582&paandie=true&dealMarker=n5HdZvsqH8RXHZEDY1p-0Q2_yROw6rOccJ-oaDqSI4E-qXbu1aDx8aCQaGPjzYRw) ## Ready to book your vacation to Sleepy Hollow? Choose your dates ## Sleepy Hollow Hotel Deals ![DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove](https://images.trvl-media.com/lodging/1000000/10000/6600/6545/8dd24dc8_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove 1200 N Mittel Blvd, Wood Dale, IL Fully refundableReserve now, pay when you stay CA $137 CA $152 total Oct 19 - Oct 20 includes taxes & fees 8/10 Very Good! (1,018 reviews) "Very clean" Reviewed on Oct 6, 2025 [](https://expedia.ca/Hotel-Search?startDate=19%2F10%2F2025&endDate=20%2F10%2F2025&selected=6545&PinnedHotelID=6545&HadPinnedHotel=true®ionId=3000435324) ![Courtyard by Marriott Chicago Wood Dale](https://images.trvl-media.com/lodging/1000000/10000/3100/3034/400d8a7d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Courtyard by Marriott Chicago Wood Dale 900 N Wood Dale Rd, Wood Dale, IL CA $130 CA $144 total Oct 19 - Oct 20 includes taxes & fees 8.4/10 Very Good! (1,003 reviews) "Easy and plenty parking" Reviewed on Oct 6, 2025 [](https://expedia.ca/Hotel-Search?startDate=19%2F10%2F2025&endDate=20%2F10%2F2025&selected=3034&PinnedHotelID=3034&HadPinnedHotel=true®ionId=3000435324) ![Eaglewood Resort and Spa](https://images.trvl-media.com/lodging/1000000/900000/897200/897168/f931dcd0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Eaglewood Resort and Spa 1401 Nordic Rd, Itasca, IL Fully refundableReserve now, pay when you stay CA $144 CA $190 total Nov 9 - Nov 10 includes taxes & fees 8.6/10 Excellent! (1,001 reviews) "Great place" Reviewed on Oct 2, 2025 [](https://expedia.ca/Hotel-Search?startDate=09%2F11%2F2025&endDate=10%2F11%2F2025&selected=897168&PinnedHotelID=897168&HadPinnedHotel=true®ionId=3000435324) [See all 486 properties in Sleepy Hollow](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=12%2F10%2F2025&endDate=13%2F10%2F2025®ionId=3000435324) 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 ![QR code to download the app](data:image/png;base64,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)