Sleepy Hollow Vacations from ₩816,978
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- Better togetherSave up to ₩1,660,000 when you book a flight and hotel together*
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The Latest Sleepy Hollow Vacation Packages
- The Whitehall Hotel, BW Premier Collection
Sep 19 - Sep 22The Whitehall Hotel, BW Premier Collection + Flight
Downtown Chicago3 nights3.5 star property8.4/10 - Very Good (3,916 reviews)"Good stay, one of the desk staff was less than pleasant to talk to. Every time she was not easy to approach and less than helpful. I enjoyed my stay and the room was great. Old wood everywhere which I enjoyed. It was weird when they had their breakfast because they were put out pastries but then in the middle, they put out something that was much nicer but only a few of them not enough for everybody. Sorry it was a little bit weird if you weren’t there at the right time you missed out on..."Reviewed July 29, 2026Roundtrip • New York (EWR) - Chicago (ORD)LGA - ORD • Nonstop ORD - LGA • Nonstop - Hotel Riu Plaza Chicago
Sep 19 - Sep 22Hotel Riu Plaza Chicago + Flight
Downtown Chicago3 nights4.0 star property9.4/10 - Exceptional (4,855 reviews)Roundtrip • New York (EWR) - Chicago (ORD)LGA - ORD • Nonstop ORD - LGA • Nonstop - Pendry Chicago
Sep 19 - Sep 22Pendry Chicago + Flight
Downtown Chicago3 nights4.5 star property9.2/10 - Wonderful (1,152 reviews)"The property is one of the coolest places in Chicago. Conveniently located to the Magnificent Mile, Millennial Park, and the Theater District."Reviewed July 28, 2026Roundtrip • New York (EWR) - Chicago (ORD)LGA - ORD • Nonstop ORD - LGA • Nonstop - Swissotel - Chicago
Sep 19 - Sep 22Swissotel - Chicago + Flight
Downtown Chicago3 nights4.5 star property9.0/10 - Wonderful (3,512 reviews)Roundtrip • New York (EWR) - Chicago (ORD)LGA - ORD • Nonstop ORD - LGA • Nonstop - Sable at Navy Pier Chicago, Curio Collection by Hilton
Sep 19 - Sep 22Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight
Downtown Chicago3 nights4.0 star property9.4/10 - Exceptional (2,634 reviews)"They let us check in early which was wonderful! Staff were extremely friendly and the valet was more than kind when I forgot a few items in my car. The room was clean and beautiful 😍"Reviewed July 28, 2026Roundtrip • New York (EWR) - Chicago (ORD)LGA - ORD • Nonstop ORD - LGA • Nonstop
Frequently Asked Questions
How much does a Sleepy Hollow vacation package cost?
Get your credit card ready, because a getaway to Sleepy Hollow starts from a tempting ₩816,978. When you bundle your flights, hotels and more into a package, you'll land the lowest prices.
How do I get a cheap travel package to Sleepy Hollow?
Book everything in the one place with our Sleepy Hollow vacation packages. We have incredible bargains on hotels, flights, tours and more that'll keep your travel budget happy and your adventurous spirit alive. And, with more than 550 partner airlines and 1,000,000 hotel options around the world to pick from, there are endless opportunities to mix and match as you like.
Where should I stay in Sleepy Hollow?
There's plenty to do in Sleepy Hollow, so stay near its best attractions and spend more time sightseeing. Balzekas Museum of Lithuanian Culture is one spot to put on your must-see list.
How far in advance should I book my Sleepy Hollow vacation?
Reserving your flights early with Expedia means one less thing to worry about. A number of air carriers advertise prices up to 12 months in advance. This is usually the cheapest time to book. If circumstances have left you booking late, fantastic last-minute deals to Sleepy Hollow sometimes emerge a few weeks before departure.
What does an Expedia Sleepy Hollow travel package include?
Expedia has everything you need to lock in Sleepy Hollow trip, but what goes into your package is your call. Select from any combination of rental cars, flights and hotels. Chasing some experiences or tours to keep you on the go? Once you've made your booking, you can add them on too. No matter your style, there's a package to meet your needs.
What should I know before booking a Sleepy Hollow travel package?
Booking all the parts of your getaway together is a great way to save. Bundle your airfares, rental cars and hotels into a neat package. But your options don't end at hotels. Expedia has all kinds of properties, including vacation rentals like beachside villas and city apartments. You've got choices galore!
Can I choose my airline with a Sleepy Hollow Expedia vacation package?
Expedia has access to more than 550 airline partners worldwide, so you definitely can. Simply select the carrier that suits you and craft your ideal Sleepy Hollow getaway.
If I'm not able to travel, can I cancel my Sleepy Hollow vacation package?
Certainly, and we'll help you every step of the way. You may be able to cancel or amend your Sleepy Hollow vacation package at no cost if you booked in the last 24 hours. But you may incur a fee from your hotel, airline or car rental company for older bookings. If your travel plans unexpectedly change, have a look at our Customer Service Portal for more information.