Sleepy Hollow Holidays

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Our guide on 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 featuring a city

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

Our pick of the best 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 NZ$263 per night from 14 Feb to 15 Feb
NZ$263
14 Feb - 15 Feb
includes taxes & fees
8/10 Very Good! (9,821 reviews)
Yes perfectly clean

Reviewed on 24 Jan 2026

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 NZ$206 per night from 5 Feb to 6 Feb
NZ$206
5 Feb - 6 Feb
includes taxes & fees
8.4/10 Very Good! (5,614 reviews)
Too few elevators working…

Reviewed on 28 Jan 2026

Embassy Suites by Hilton Chicago Downtown River North
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
300 E Ohio St Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$166 per night from 3 Feb to 4 Feb
NZ$166
3 Feb - 4 Feb
includes taxes & fees
8.6/10 Excellent! (2,266 reviews)
Great

Reviewed on 27 Jan 2026

DoubleTree by Hilton Chicago - Magnificent Mile
See all 4,972 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 holiday package cost?
Get your credit card ready, because a getaway to Sleepy Hollow starts from a tempting . 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 holiday 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 holiday?
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 holiday homes like beachside villas and city apartments. You've got choices galore!
Can I choose my airline with a Sleepy Hollow Expedia holiday 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 holiday package?
Certainly, and we'll help you every step of the way. You may be able to cancel or amend your Sleepy Hollow holiday 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 which includes a city, central business district and a sporting event

Wrigley Field

4.5/5(21 reviews)

A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.

Wrigley Field
McCormick Place showing a high rise building and a city

McCormick Place

4.5/5(21 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
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(64 reviews)

One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

Navy Pier

Activities

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

NZ$43
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Lineup with Capone and Dillinger!

Chicago Crime and Mob Bus Tour

NZ$85
per adult
92% of travellers recommend
Chicago Crime and Mob Bus Tour
Art Institute of Chicago

Art Institute of Chicago

NZ$70
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.