Sleepy Hollow Vacations from ￥289,670

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The Latest Sleepy Hollow Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Jul 12 - Jul 15
Roundtrip flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (687 reviews)
Enjoyed our stay at the Pendry. It is in a great location and very walkable. Housekeeping was great. Enjoyed the restaurant and bar and the staff was very friendly.

Reviewed on May 15, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Jul 12 - Jul 15
Roundtrip flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (1,190 reviews)
The best hotel hands down!

Reviewed on May 13, 2024

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
Jul 12 - Jul 15
Roundtrip flight included
Tokyo (NRT) to Chicago (ORD)
9.8/10 Exceptional! (1,012 reviews)
I was pleasantly surprised to find artwork displayed throughout the property, including my favorite Kehinde Wiley.

Reviewed on May 12, 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Jul 12 - Jul 15
Roundtrip flight included
Tokyo (NRT) to Chicago (ORD)
8.8/10 Excellent! (207 reviews)
Thoroughly enjoyed my stay and my room. Will definitely book here again. Basic view of the courtyard but that was not important to me.

Reviewed on Mar 16, 2024

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Jul 12 - Jul 15
Roundtrip flight included
Tokyo (NRT) to Chicago (ORD)
9.6/10 Exceptional! (976 reviews)
Everything exceeded our expectations and would highly recommend! Stunning rooms that make the Ritz and Four Seasons look pathetic!

Reviewed on May 2, 2024

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 showing a city

Downtown Chicago

4 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

Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥15,539 per night from May 27 to May 28
￥15,539
per night
May 27 - May 28
7.6/10 Good! (2,584 reviews)
"Large, super clean, convenient hotel. Staff was excellent and friedly. Bar staff was great. Would definitely stay again."

Reviewed on May 16, 2024

Warwick Allerton - Chicago
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 ￥23,094 per night from May 27 to May 28
￥23,094
per night
May 27 - May 28
7.6/10 Good! (6,728 reviews)
"I really liked how clean the room was."

Reviewed on May 14, 2024

Congress Plaza Hotel
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥34,652 per night from Jun 6 to Jun 7
￥34,652
per night
Jun 6 - Jun 7
8.6/10 Excellent! (1,001 reviews)
"We had a wonderful time in Chicago! This property was located in such a great area and easy walking to all the things we wanted to do...and eat. :)"

Reviewed on May 10, 2024

The Westin Michigan Avenue Chicago
See all 4,362 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.

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 ￥289,670. 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

Image for Wrigley Field

Wrigley Field

4.5/5(2,128 reviews)

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

Wrigley Field
Image for McCormick Place

McCormick Place

4.5/5(1,805 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Image for Six Flags Great America

Six Flags Great America

4.5/5(347 reviews)

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America

Things to do

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

￥27,764
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
See all activities in Chicago

Other vacations you might like

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