Sleepy Hollow Vacations

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Price found within the past 48 hours. Click for updated prices.
  • Room service - dining
    Jul 15 - Jul 20

    The Wade + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    8.4/10 - Very Good (1,846 reviews)
    "Bathroom doors do not close completely, beds were small than queen size, there is no microwave, fan in bathroom is not strong."
    Reviewed May 25, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥455,390
    ￥353,707
    per traveler
    found 2 hours ago
    The Wade
  • Terrace/patio
    Jul 15 - Jul 20

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.6/10 - Exceptional (1,886 reviews)
    "Location, cleanliness, overall staff assistance and service and of course breakfast"
    Reviewed May 26, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥548,170
    ￥435,320
    per traveler
    found 2 hours ago
    Trump International Hotel & Tower Chicago
  • Exterior detail
    Jul 30 - Aug 5

    The Emily Hotel + Flight

    Downtown Chicago
    6 nights
    4.0 star property
    9.2/10 - Wonderful (1,324 reviews)
    "One of the worst hotel rooms I have stayed in. Tables and drawers made out of plywood, very uncomfortable beds, tv was mounted on side of bed so you had to turn to side to watch it. Low lights, makeup light mounted on opposite side of plug in so you had a cord in front of the mirror. Super basic and not worth the price. Location, bar and coffee were only positives. Would not stay here again."
    Reviewed May 26, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥565,609
    ￥456,772
    per traveler
    found 13 hours ago
    The Emily Hotel
  • Dinner served
    Jul 15 - Jul 20

    Kimpton Gray Hotel by IHG + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.4/10 - Exceptional (1,006 reviews)
    "Great hotel. Loved the lobby and our room. Would definitely stay here again."
    Reviewed May 19, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥444,254
    ￥365,090
    per traveler
    found 2 hours ago
    Kimpton Gray Hotel by IHG
  • Lobby
    Jul 15 - Jul 20

    The Langham, Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.8/10 - Exceptional (1,001 reviews)
    "Thumbs up"
    Reviewed May 18, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥566,982
    ￥473,233
    per traveler
    found 2 hours ago
    The Langham, Chicago

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

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

Sleepy Hollow Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is ￥21,480 per night from May 27 to May 28
￥21,480
￥25,539 total
May 27 - May 28
includes taxes & fees
8/10 Very Good! (10,141 reviews)
"Everything was perfect. Great customer service."

Reviewed on May 25, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
The price is ￥37,986 per night from Jun 16 to Jun 17
￥37,986
￥49,692 total
Jun 16 - Jun 17
includes taxes & fees
9.4/10 Exceptional! (4,253 reviews)
"The hotel is clean and in a good location. The bathrooms are spacious and the showers were excellent. The rooms, however, are long, narrow, and cheaply furnished, with awkward closets and water-restricted faucets. The hotel feels designed to cut costs, without passing any savings to guests. Tile ..."

Reviewed on May 26, 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
The price is ￥30,279 per night from Jun 3 to Jun 4
￥30,279
￥35,999 total
Jun 3 - Jun 4
includes taxes & fees
7.8/10 Good! (1,477 reviews)
"El staff es un poco malhumorado Cuando tienes preguntas, la mayoria. Los tickets de comida o drinks gratis en realidad son descuentos, tienes q pagar. Excepto por el desayuno, solo use una vez cada uno, no me agrado, sali afuera. Regrese todos los demas tickets al hacer checkout. Gracias"

Reviewed on May 26, 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,847 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 . 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

Wrigley Field

Wrigley Field

4.5/5(2,149 reviews)

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

4.5/5(461 reviews)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

4.5/5(4,925 reviews)

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

Navy Pier

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥4,236
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

￥6,904
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

￥6,276
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.