Sleepy Hollow Holidays

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    Save up to Rp173.195 when you book a flight and hotel together*

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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

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

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 Rp4.519.200 per night from 13 Mar to 14 Mar
Rp4.519.200
Rp5.305.089 total
13 Mar - 14 Mar
includes taxes & fees
8/10 Very Good! (9,937 reviews)
Shortly after our check in when noticed our room did not have heat called the operator only to be told the hotels boiler was out, had to call a 2nd time because the toilet wouldn't flush finally when the maintenance guy came to fix the toilet he said he could get us a space heater we was so excited ...

Reviewed on 26 Feb 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is Rp2.087.153 per night from 8 Mar to 9 Mar
Rp2.087.153
Rp2.924.350 total
8 Mar - 9 Mar
includes taxes & fees
9.4/10 Exceptional! (3,416 reviews)
Loved the hotel and ambiance. My stay was truly amazing. I just wish they would’ve had an ice machine and microwaves inside the hotel . It would’ve been 5 stars if they had microwaves and ice. Also the receptionist attitude wasn’t the best. I didn’t feel very welcomed and seemed like she was just ...

Reviewed on 26 Feb 2026

Hotel Riu Plaza Chicago
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 Rp1.724.973 per night from 4 Mar to 5 Mar
Rp1.724.973
Rp2.024.946 total
4 Mar - 5 Mar
includes taxes & fees
8.6/10 Excellent! (5,685 reviews)
Service was great, and the staff was very kind.

Reviewed on 26 Feb 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,940 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 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

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

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

Wrigley Field
Millennium Park which includes autumn colours, modern architecture and street scenes

Millennium Park

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Grant Park showing a garden and night scenes

Grant Park

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

Things to do

Art Institute of Chicago

Art Institute of Chicago

Rp672.960
per adult
92% of travellers recommend
Art Institute of Chicago
Picture 7 for Activity Chicago River: 1.5-Hour Guided Architecture Cruise

Chicago River: 1.5-Hour Guided Architecture Cruise

Rp740.256
per adult
98% of travellers recommend
Chicago River: 1.5-Hour Guided Architecture Cruise
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

Rp1.783.344
per adult
88% of travellers recommend
Chicago C3® by CityPASS®
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.