Title: Sleepy Hollow Vacation Packages 2026 from $525 | Expedia.com [Sleepy Hollow Travel Guide](https://expedia.com/Sleepy-Hollow.dx3000435324)[Hotels in Sleepy Hollow](https://expedia.com/Sleepy-Hollow-Hotels.d3000435324.Travel-Guide-Hotels)[Vacation Rentals in Sleepy Hollow](https://expedia.com/Sleepy-Hollow-Vacation-Rentals.d3000435324.Travel-Guide-VacationRentals)[Flights to Sleepy Hollow](https://expedia.com/Cheap-Flights-To-Sleepy-Hollow.d3000435324.Travel-Guide-Flights)[Things to do in Sleepy Hollow](https://expedia.com/Things-To-Do-In-Sleepy-Hollow.d3000435324.Travel-Guide-Activities)[Car Rentals in Sleepy Hollow](https://expedia.com/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 Vacations from $525 ## Book a Hotel + Flight or Car together to unlock savings ## 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.com/Grand-Victoria-Casino-Elgin.d6065129.Vacation-Attraction), [Santas Village](https://www.expedia.com/Santas-Village-East-Dundee.d553248621532658557.Vacation-Attraction) and [NOW Arena](https://www.expedia.com/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. ## The Latest Sleepy Hollow vacation packages Price found within the past 48 hours. Click for updated prices. ![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 Save 100% on your flight $525 per person May 12 - May 15 found 1 day ago Roundtrip flight included Dallas (DAL) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) Great location. Clean, comfortable, friendly staff. Reviewed on Mar 30, 2026 ![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/7aab5ae1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### LondonHouse Chicago, Curio Collection by Hilton Downtown Chicago Save 100% on your flight $1,122 per person Jun 4 - Jun 8 found 1 day ago Roundtrip flight included Dallas (DFW) to Chicago (ORD) 9.4/10 Exceptional! (3,646 reviews) Super clean, super friendly staff. Reviewed on Mar 29, 2026 ![Hilton Garden Inn Chicago Downtown South Loop](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/d5b5d773_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Garden Inn Chicago Downtown South Loop Downtown Chicago Save 100% on your flight $1,030 per person Jun 4 - Jun 8 found 5 hours ago Roundtrip flight included Dallas (DFW) to Chicago (ORD) 8.8/10 Excellent! (1,894 reviews) The valet and front desk staff were friendly Reviewed on Mar 30, 2026 ![Thompson Chicago, by Hyatt](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/8920c075_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Thompson Chicago, by Hyatt Downtown Chicago Save 100% on your flight $1,008 per person Jun 4 - Jun 8 found 1 day ago Roundtrip flight included Dallas (DFW) to Chicago (ORD) 9.2/10 Wonderful! (1,332 reviews) Perfect area- close to everything! Reviewed on Mar 29, 2026 Don't see what you're looking for? See all available trips from Columbus to Sleepy Hollow [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Sleepy Hollow Hotel Deals ![Comfort Inn & Suites Arlington Heights - Schaumburg](https://images.trvl-media.com/lodging/1000000/900000/894900/894864/d2adf0b5_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Comfort Inn & Suites Arlington Heights - Schaumburg 2112 S Arlington Heights Rd Arlington Heights IL $94 nightly $105 total Apr 20 - Apr 21 Total with taxes and fees 8.2/10 Very Good! (1,090 reviews) The nozzle in shower was broken and I asked them to fix it…it was not fixed. Coming back to room after a long day to it still non functional was a tad frustrating. Line was long in lobby so I sucked it up and treated it as a camping trip. Reviewed on Mar 29, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F20%2F2026&endDate=4%2F21%2F2026&selected=894864&PinnedHotelID=894864&HadPinnedHotel=true®ionId=3000435324) ![Quality Inn Schaumburg - Chicago near the Mall](https://images.trvl-media.com/lodging/1000000/10000/8500/8404/021474fc_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Quality Inn Schaumburg - Chicago near the Mall 600 North Martingale Rd Schaumburg IL Fully refundableReserve now, pay when you stay $76 nightly $87 total Apr 23 - Apr 24 Total with taxes and fees 8.6/10 Excellent! (1,007 reviews) nice location close to the Northwest Transportation Center you can walk there 1 minute and take the Pace to Rosemont blue line to Ohare airport so you really dont need a car uber, lyft or arrange a car rental there Reviewed on Mar 30, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F23%2F2026&endDate=4%2F24%2F2026&selected=8404&PinnedHotelID=8404&HadPinnedHotel=true®ionId=3000435324) ![Eaglewood Resort and Spa](https://images.trvl-media.com/lodging/1000000/900000/897200/897168/c603e0d7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Eaglewood Resort and Spa 1401 Nordic Rd Itasca IL Fully refundableReserve now, pay when you stay $144 nightly $160 total Mar 31 - Apr 1 Total with taxes and fees 8.8/10 Excellent! (1,005 reviews) Went for a birthday girlfriends weekend. The staff was friendly, the rooms were clean and provided what we needed. Our room couldve had better lighting by perhaps an extra lamp. Nice big tv, comfortable beds. The balcony was big and spacious. The buffet breakfast was very good and the overall condition ... Reviewed on Mar 30, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F31%2F2026&endDate=4%2F1%2F2026&selected=897168&PinnedHotelID=897168&HadPinnedHotel=true®ionId=3000435324) [See all 518 properties in Sleepy Hollow](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F31%2F2026&endDate=4%2F1%2F2026®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. ## Find the Best Sleepy Hollow Vacation Packages ### Things to do near Sleepy Hollow Sleepy Hollow, Illinois, is perfect for family-friendly vacations, offering a blend of outdoor activities and urban charm. Visitors can enjoy shopping at local centers and explore educational attractions. Key experiences include exciting tour packages, spooky fun, village visits, and seasonal events, ensuring a memorable getaway for all ages. **Shopping** For a great shopping experience in Sleepy Hollow, visit [Cabela's](https://www.expedia.com/Cabelas-Chicago.d553248635998039755.Vacation-Attraction), just 5 miles away, or explore the [Arboretum of South Barrington](https://www.expedia.com/Arboretum-Of-South-Barrington-Chicago.d6175734.Vacation-Attraction), 6 miles away, which offers a vibrant atmosphere. If you're up for a drive, check out the [Crystal Court Shopping Center](https://www.expedia.com/Crystal-Court-Shopping-Center-Crystal-Lake.d6183823.Vacation-Attraction), located 9 miles away, for more options. **Recreation** Experience the lush greens at [Randall Oaks Golf Club](https://www.expedia.com/Randall-Oaks-Golf-Club-West-Dundee.d553248635974846255.Vacation-Attraction), just 3 miles away, perfect for golf enthusiasts. Enjoy vibrant performances at [Hemmens Cultural Center](https://www.expedia.com/Hemmens-Cultural-Center-Elgin.d6247286.Vacation-Attraction), 4 miles from Sleepy Hollow, offering a mix of culture and entertainment. For relaxation, visit [Elgin Sports Complex](https://www.expedia.com/Elgin-Sports-Complex-Elgin.d553248635974846086.Vacation-Attraction), located 5 miles away, promoting wellness and tranquility. **Adventure** [Epic Air Trampoline Park](https://www.expedia.com/Epic-Air-Trampoline-Park-South-Elgin.d553248621532658549.Vacation-Attraction), located 8 miles from Sleepy Hollow, offers exhilarating bouncing fun for all ages with its vibrant atmosphere. For outdoor enthusiasts, [North Wall Rock Climbing](https://www.expedia.com/North-Wall-Rock-Climbing-Crystal-Lake.d553248621532659115.Vacation-Attraction), also 8 miles away, provides thrilling climbing challenges surrounded by nature. [Brunswick Zone XL](https://www.expedia.com/Brunswick-Zone-XL-Algonquin.d553248621532658559.Vacation-Attraction), 4 miles away, combines arcade games with family-friendly excitement. **Nightlife** Experience Sleepy Hollow's nightlife with cozy bars and local eateries. Enjoy live music at nearby venues and unwind at charming pubs. The atmosphere is relaxed, perfect for mingling with locals and savoring delightful drinks. Explore the nearby areas for more vibrant nightlife options under the stars. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Find the best attractions near Sleepy Hollow Sleepy Hollow, Illinois, offers a delightful mix of family-friendly and outdoor activities, making it perfect for any vacation. Explore popular attractions like the Sleepy Hollow Cemetery and local parks, as well as event venues and nature reserves. Whether you're seeking cultural experiences or simply enjoying the great outdoors, Sleepy Hollow has something for everyone to enjoy. - **[Santa's Village: ](https://www.expedia.com/Santas-Village-East-Dundee.d553248621532658557.Vacation-Attraction)** Located 2 miles from Sleepy Hollow, Santa's Village is a delightful theme park perfect for families. With whimsical rides, interactive attractions, and festive entertainment, it captures the holiday spirit year-round, ensuring joy for visitors of all ages. - **[NOW Arena: ](https://www.expedia.com/NOW-Arena-Chicago.d6192396.Vacation-Attraction)** Just 5 miles away, NOW Arena is a premier entertainment facility hosting a variety of events. From thrilling sports games to spectacular concerts, the arena offers a vibrant atmosphere perfect for family outings and memorable experiences. - **[Schaumburg Convention Center: ](https://www.expedia.com/Schaumburg-Convention-Center-Chicago.d6169684.Vacation-Attraction)** Situated 13 miles from Sleepy Hollow, this event venue is ideal for business travelers. With modern facilities and versatile spaces, it hosts conferences and events, making it a hub for professional gatherings and networking. ### Best time to go to Sleepy Hollow The best time to visit Sleepy Hollow is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly cloudy with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 22.3°F (-5.4°C) | Light Rain | Mostly Cloudy | Slightly Low | Slightly Low | | February | 24.6°F (-4.1°C) | Light Rain | Mostly Cloudy | Slightly Low | Slightly Low | | March | 37.4°F (3.0°C) | Light Rain | Mostly Cloudy | Average | Average | | April | 47.3°F (8.5°C) | Light Rain | Mostly Cloudy | Average | Average | | May | 59.4°F (15.2°C) | Light Rain | Mostly Sunny | Average | Average | | June | 68.9°F (20.5°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | July | 72.9°F (22.7°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | August | 71.4°F (21.9°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | September | 64.9°F (18.3°C) | Light Rain | Mostly Sunny | Average | Average | | October | 52.5°F (11.4°C) | Light Rain | Mostly Sunny | Average | Average | | November | 39.4°F (4.1°C) | Light Rain | Mostly Sunny | Average | Average | | December | 29.5°F (-1.4°C) | Light Rain | Mostly Cloudy | Slightly Low | Slightly Low | ### Tips to save on your trip to Sleepy Hollow - Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings. - Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Sleepy Hollow. - Use the *Price per traveler* filter on Expedia to find a package deal that suits your budget. - Check the *VIP Access properties* filter to discover outstanding hotels with added member perks at select properties. ## Sleepy Hollow Essential Information | Language | English | | --------------- | ---------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Closest Airport | O'Hare Intl. Airport (ORD) | | Population | 3,300 | | Top Sights | [Santas Village](https://www.expedia.com/Santas-Village-East-Dundee.d553248621532658557.Vacation-Attraction), [Hemmens Cultural Center](https://www.expedia.com/Hemmens-Cultural-Center-Elgin.d6247286.Vacation-Attraction) and [Epic Air Trampoline Park](https://www.expedia.com/Epic-Air-Trampoline-Park-South-Elgin.d553248621532658549.Vacation-Attraction) | ## More vacations you might like ![](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.com/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.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) 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![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Sleepy Hollow vacation package cost? ### What are the cheapest months to go to Sleepy Hollow? ### How many days is enough for Sleepy Hollow? ### How to find the best Sleepy Hollow package deals? ### Is it cheaper to book a Sleepy Hollow vacation as a package? ### When to book a vacation package to Sleepy Hollow? ### How to plan a trip to Sleepy Hollow? > 1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Sleepy Hollow. > 2. Figure out your budget: Make sure you have enough money to pay for everything from transportation and meals to activities and airfares. Your accommodations will probably be the biggest expense during your trip to Sleepy Hollow. > 3. Explore Sleepy Hollow using Expedia's [trip planning tool](https://www.expedia.com/why/trip-planning): Gain insights into the top attractions and best hotels for your trip to Sleepy Hollow. You can also save your favorite locations, collaborate with your group and manage all your plans in one place. > 4. Set the duration of your trip: Start by making a list of all the sights and activities you want to get to in Sleepy Hollow. Then, estimate how long you'll need at each, as well as any travel time. > 5. Bundle your accommodations and airfare: Once you've settled on your dates and duration, book the perfect Sleepy Hollow vacation package for you. > 6. Book any activities or excursions: Now to the fun part — organizing everything you want to see and do. Explore some of the top [things to do in Sleepy Hollow](https://www.expedia.com/Things-To-Do-In-Sleepy-Hollow.d3000435324.Travel-Guide-Activities) in Sleepy Hollow and reserve your tickets early to save time (and maybe some cash too!). ### Does Expedia offer Book Now, Pay Later Sleepy Hollow vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - More ways to book - [West Dundee Hotels ](https://www.expedia.com/West-Dundee-Hotels.d172781.Travel-Guide-Hotels) - [Apartments in West Dundee ](https://www.expedia.com/West-Dundee-Apartments.d172781-aaApartments.Travel-Guide-Accommodation) - [Casino Hotels in West Dundee ](https://www.expedia.com/West-Dundee-Hotels-Casino-Hotel.0-0-d172781-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in West Dundee ](https://www.expedia.com/West-Dundee-Hotels-Romantic-Hotel.0-0-d172781-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Hotels with an Outdoor Pool in West Dundee ](https://www.expedia.com/West-Dundee-Hotels-Hotels-With-Outdoor-Pool.0-0-d172781-tHotelswithOutdoorPool.Travel-Guide-Filter-Hotels) - 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