Sleepy Hollow Holidays

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Price found within the past 48 hours. Click for updated prices.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
27 Dec - 30 Dec
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
9/10 Wonderful! (809 reviews)
It was a nice experience. The hotel was very clean and the staff was very welcoming.

Reviewed on 16 Nov,2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
27 Dec - 30 Dec
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (1,390 reviews)
Excellent , nice city room view ,

Reviewed on 15 Nov,2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
27 Dec - 30 Dec
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
9/10 Wonderful! (263 reviews)
Beautiful place with amazing amenities. Perfect stay for adults or families alike! Highly recommend!

Reviewed on 11 Nov,2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
27 Dec - 30 Dec
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (888 reviews)
We thoroughly enjoyed our stay. The staff was courteous and attentive, the room was clean, modern, and comfortable.

Reviewed on 14 Nov,2024

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
27 Dec - 30 Dec
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (3,559 reviews)
excellent staff, great lounge and location

Reviewed on 14 Nov,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 featuring a city

Downtown Chicago

5 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Top hotels in Sleepy Hollow

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 S$135 per night from 24 Nov to 25 Nov
S$135
includes taxes & fees
24 Nov - 25 Nov
7.8/10 Good! (8,084 reviews)
"I did really enjoy my stay at the congress hotel overall, 1.st I’m going to say I love the history behind the building and the architecture. It kinda looks like the Stanley hotel on a budget while you’re walking to your room which I’m not complaining I did love the experience. 2. If you’re going ..."

Reviewed on 16 Nov,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 S$186 per night from 8 Dec to 9 Dec
S$186
includes taxes & fees
8 Dec - 9 Dec
8.2/10 Very Good! (3,200 reviews)
"It was great being in a hotel central to the city and close to a lot of things. The breakfast was amazing!"

Reviewed on 15 Nov,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 S$153 per night from 16 Dec to 17 Dec
S$153
includes taxes & fees
16 Dec - 17 Dec
8.6/10 Excellent! (3,544 reviews)
"This hotel is a wonderful place, I was there around 8:00 on the 14th of November and The Man Behind The Desk was exceptional! He went above and beyond to get me the room that I was asking for. I did not get the gentleman's name but this hotel needs more people just like him. The River Hotel on Wacker ..."

Reviewed on 16 Nov,2024

River Hotel
See all 4,265 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 S$707. 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 rentals 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.

Popular places to visit

McCormick Place

McCormick Place

4.5/5(36 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
Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

4.5/5(40 reviews)

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

4.5/5(147 reviews)

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

Things to do

Flyover in Chicago

Flyover in Chicago

S$50
Per adult
94% of travellers recommend
Flyover in Chicago
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

S$58
Per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Cocktail Cruise

Chicago River Cocktail Cruise

S$78
Per adult
90% of travellers recommend
Chicago River Cocktail Cruise
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.