Sleepy Hollow Vacation Packages

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Sleepy Hollow

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
The Wade
Park Hyatt Chicago
Level Chicago - River North
Chicago Athletic Association, a Hyatt Hotel

Where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas and neighborhoods for the activities you enjoy most. Learn more about Sleepy Hollow

Sleepy Hollow Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $177 per night from Aug 18 to Aug 19
CA $177
CA $207 total
Aug 18 - Aug 19
includes taxes & fees
7.8/10 Good! (8,916 reviews)
"Great views of the lake. Good location for museum campus and northerly island."

Reviewed on Aug. 14, 2025

Congress Plaza Hotel
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $209 per night from Sep 1 to Sep 2
CA $209
CA $245 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (1,184 reviews)
"Very nice place close to so many places."

Reviewed on Aug. 15, 2025

The Wade
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $222 per night from Aug 24 to Aug 25
CA $222
CA $261 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (4,711 reviews)
"Happy Hour drinks were amazing!"

Reviewed on Aug. 16, 2025

Embassy Suites by Hilton Chicago Downtown River North
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.

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 CA $681. 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.

Discover the most popular places to visit in Sleepy Hollow

Things to do

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.