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

Top Holiday Package Deals in Sleepy Hollow

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,900, price is now CA $1,360 per person
CA $1,360
per person
Jun 3 - Jun 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (453 reviews)
I booked this stay specifically because I saw they had a steam room and Sauna. They were both very pleasant and available 24/7. The room was very high quality with great views but if the city. The game rooms looked really nice and spacious but I sadly didn’t have time to enjoy that aspect of the hotel. There is also a great cafe and bakery connected to the lobby. I’m excited to book here again with a little more time to make the most of my stay

Reviewed on Apr 11, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $3,272, price is now CA $2,122 per person
CA $2,122
per person
May 14 - May 18
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
Great location! Easy parking and the rooms were gorgeous! We will definitely stay here next time we visit Chicago

Reviewed on Apr 10, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $2,647, price is now CA $1,868 per person
CA $1,868
per person
May 14 - May 18
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
We love staying at the Sable. Easy in and out parking. The Valet staff is wonderful. We enjoyed our breakfast. The room and view is always amazing.

Reviewed on Apr 11, 2026

Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was CA $2,134, price is now CA $1,509 per person
CA $1,509
per person
Jun 19 - Jun 23
found 12 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
8.8/10 Excellent! (1,013 reviews)
Le Meridien Exxex Chicago is in the perfect location, steps from where I need to be when visiting Chicago. The staff are super helpful and friendly. The restaurant serves delicious food and the waitstaff is attentive. Keep up the good work!

Reviewed on Apr 3, 2026

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was CA $2,415, price is now CA $1,715 per person
CA $1,715
per person
May 20 - May 27
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.2/10 Wonderful! (371 reviews)
Breakfast was good. Room was clean with great air-conditioned. Staff very nice and happy. Customer service great. Had a great experience. Will be back and would recommend to everyone.

Reviewed on Apr 11, 2026

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
Downtown Chicago

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

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 $171 per night from Apr 26 to Apr 27
CA $171
CA $200 total
Apr 26 - Apr 27
includes taxes & fees
8/10 Very Good! (10,095 reviews)
Storage luggage staff was great and helpful. Had to move rooms due to the shower being dirty and water was not draining. Second room had brown water coming out when you turned the shower on, after 5 minutes it would go away.

Reviewed on Apr 11, 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $165 per night from Apr 26 to Apr 27
CA $165
CA $194 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (4,107 reviews)
Don’t book through Expedia, I had to leave my vacation early because I had to rush my travel companion to the ER as they were struggling to breathe. Great hotel, just don’t book through Expedia. You will have problems.

Reviewed on Apr 11, 2026

Hilton Chicago/Magnificent Mile Suites
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 $192 per night from Apr 26 to Apr 27
CA $192
CA $225 total
Apr 26 - Apr 27
includes taxes & fees
8.6/10 Excellent! (5,842 reviews)
Great location!

Reviewed on Apr 11, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,898 properties in Sleepy Hollow
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 $1,360. 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

Wrigley Field

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $60
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
See all activities in Chicago

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.