Sleepy Hollow Vacations from $368

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Your Sleepy Hollow Vacation

Experience everything this neighborhood has to offer with a tailor-made Sleepy Hollow vacation package. However you picture yourself spending your time here, you'll find endless opportunities for fun, relaxation and adventure. What to cross off your itinerary first? Nearby Balzekas Museum of Lithuanian Culture is one thing you can't miss during your trip to Sleepy Hollow. Expedia will help turn your dream Sleepy Hollow vacation into reality, whatever your travel plans or budget.

The Latest Sleepy Hollow Vacation Packages

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $726, price is now $368 per person
$368
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel

Reviewed on Oct 20, 2025

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,151, price is now $457 per person
$457
per person
Dec 21 - Dec 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,070 reviews)
location to everything

Reviewed on Oct 30, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $1,010, price is now $474 per person
$474
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
We loved the Pendry!

Reviewed on Oct 27, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $746, price is now $368 per person
$368
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Loved my stay here. Everything was top notch from the time I entered the lobby. The staff was welcoming and enthusiastic about you choosing to patronize their hotel. The check-in process was quick. The hotel’s rooms were very clean and had the latest amenities. Televisions had numerous channel options. The roof top bar was amazing for photo ops. It’s also in a very good location for site seeing & shopping.

Reviewed on Oct 31, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was $796, price is now $404 per person
$404
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (303 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.

Reviewed on Oct 28, 2025

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

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

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
$118 nightly
The price is $139 total per night from Nov 23 to Nov 24
$139 total
Nov 23 - Nov 24
Total with taxes and fees
8.4/10 Very Good! (5,180 reviews)
Amazing amenities, cleanness and quite space

Reviewed on Nov 1, 2025

Embassy Suites by Hilton Chicago Downtown River North
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $129 total per night from Nov 25 to Nov 26
$129 total
Nov 25 - Nov 26
Total with taxes and fees
7.8/10 Good! (9,648 reviews)
Adequate

Reviewed on Nov 1, 2025

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $119 total per night from Nov 17 to Nov 18
$119 total
Nov 17 - Nov 18
Total with taxes and fees
8.8/10 Excellent! (3,214 reviews)
Great staff, great location and appreciate responsiveness as needed.

Reviewed on Nov 1, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,845 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Sleepy Hollow

Wrigley Field featuring cbd, a sporting event and a city

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
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

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

River tour boat in Chicago

Architecture River Tour

$49
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

$44
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.