Sleepy Hollow Vacations

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Your Sleepy Hollow Vacation

Make travel planning hassle-free by snapping up a vacation package to Sleepy Hollow. Let us handle the minutiae, so you can focus on savoring everything this neighborhood has to offer. Your trip to Sleepy Hollow wouldn't be complete without exploring leading attractions nearby such as Morton College, Hawthorne Works Museum and Balzekas Museum of Lithuanian Culture. Whatever your travel plans or the size of your budget, booking your ideal Sleepy Hollow vacation is simple with Expedia.

The Latest Sleepy Hollow Vacation Packages

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

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 30 - Sep 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,007 reviews)
One of the best hotels Ive ever been to and such a clean and beautiful city

Reviewed on Jun 17, 2024

W Chicago - Lakeshore

W Chicago - Lakeshore

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 30 - Sep 6
found 14 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.2/10 Very Good! (1,006 reviews)
Good stay at the W, staff was very nice and organized. Would stay there again for sure.

Reviewed on Jun 17, 2024

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 6 - Sep 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (97 reviews)
Staff was very friendly and helpful.

Reviewed on Jun 15, 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 30 - Sep 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (216 reviews)
I found out that the problem is more me - i am just not a fan of central Chicago - too much traffic-sirens etc., Otherwise the hotel and amenities were fine.

Reviewed on Jun 18, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 30 - Sep 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,230 reviews)
Location is amazing, super friendly staff. Will definitely be back soon

Reviewed on Jun 17, 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 hotel + flight trips 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 $161 per night from Jul 1 to Jul 2
$161
$189 total
includes taxes & fees
Jul 1 - Jul 2
7.6/10 Good! (7,005 reviews)
"I love the history of this hotel. Like a grand old hotel from the past. Also you can’t beat the price or location. The staff was especially friendly and helpful!"

Reviewed on Jun 18, 2024

Congress Plaza Hotel
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 $182 per night from Jul 1 to Jul 2
$182
$213 total
includes taxes & fees
Jul 1 - Jul 2
8/10 Very Good! (2,400 reviews)
Great stay loved it
"Love staying at the embassy suits. Breakfast as well as there social hour"

Reviewed on Jun 18, 2024

Embassy Suites by Hilton Chicago Downtown River North
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $159 per night from Jun 30 to Jul 1
$159
$187 total
includes taxes & fees
Jun 30 - Jul 1
8.6/10 Excellent! (2,956 reviews)
"Great central location"

Reviewed on Jun 18, 2024

River Hotel
See all 4,305 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly 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 $506. 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 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
Image for Navy Pier

Navy Pier

4.5/5(4,870 reviews)

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

Navy Pier

Things to do

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

$188
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
Image for Chicago Architecture Center River Cruise aboard Chicago's First Lady

Chicago Architecture Center River Cruise aboard Chicago's First Lady

$54
Per adult
96% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
Image for Chicago Pizza Tour

Chicago Pizza Tour

$89
Per adult
100% of travellers recommend
Chicago Pizza Tour
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.