Deals on vacations and trips to Sleepy Hollow

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Sleepy Hollow flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Hyatt House Chicago West Loop

Hyatt House Chicago West Loop

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $455, price is now $273 per person
$273
per person
Feb 4 - Feb 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and free buffet breakfast each morning.
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,177, price is now $516 per person
$516
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and coffee shop.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,603, price is now $918 per person
$918
per person
Dec 28 - Jan 2
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.
Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $736, price is now $431 per person
$431
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the express check-out, laundry service, and valet parking. There's luggage storage and multilingual staff can provide around-the-clock assistance.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,522, price is now $918 per person
$918
per person
Dec 28 - Jan 2
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.

Top Sleepy Hollow hotels deals

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

4 out of 5
1200 N Mittel Blvd Wood Dale IL
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $99 total per night
$99 total
Nov 26 - Nov 27
Total with taxes and fees
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Pool
Pet friendly
Wyndham Garden Schaumburg Chicago Northwest

Wyndham Garden Schaumburg Chicago Northwest

3 out of 5
1725 E Algonquin Road Schaumburg IL
Free Cancellation
Reserve now, pay when you stay
$63 nightly
The price is $73 total per night
$73 total
Nov 23 - Nov 24
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the 24-hour business center, conference space, and airport shuttle. There's a 24-hour gym on site, and a 24-hour front desk and a terrace are also provided.
Parking included
Free WiFi
Courtyard by Marriott Chicago Wood Dale

Courtyard by Marriott Chicago Wood Dale

3 out of 5
900 N Wood Dale Rd Wood Dale IL
Free Cancellation
Reserve now, pay when you stay
$80 nightly
The price is $89 total per night
$89 total
Nov 28 - Nov 29
Total with taxes and fees
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and free airport shuttle. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Pool
Free airport shuttle
Eaglewood Resort and Spa

Eaglewood Resort and Spa

4 out of 5
1401 Nordic Rd Itasca IL
Free Cancellation
Reserve now, pay when you stay
$97 nightly
The price is $107 total per night
$107 total
Nov 27 - Nov 28
Total with taxes and fees
This smoke-free resort features a golf course, a full-service spa, and 2 restaurants. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Make the most of the outdoor pool and indoor pool, and relax with drinks at one of the 2 bars/lounges.
Pool
Hot Tub
Motel 6 Elk Grove Village, IL

Motel 6 Elk Grove Village, IL

2 out of 5
1000 W Devon Ave Elk Grove Village IL
Free Cancellation
$45 nightly
The price is $51 total per night
$51 total
Nov 26 - Nov 27
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A computer station is provided and the front desk is staffed around-the-clock.
Pet friendly
Parking included
Comfort Inn & Suites Arlington Heights - Schaumburg

Comfort Inn & Suites Arlington Heights - Schaumburg

3 out of 5
2112 S Arlington Heights Rd Arlington Heights IL
$59 nightly
The price is $66 total per night
$66 total
Dec 21 - Dec 22
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Parking included
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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 are vacation packages to Sleepy Hollow?
Travelocity provides package deals to Sleepy Hollow, as well as flights and hotels, starting at just $273. With all the money you save, you could book some interesting tours or perhaps even add some extra nights to your getaway.
Where can I get the best vacation package deals for Sleepy Hollow?
It's simple — head to Travelocity. With as many as 400 partner airlines and 1,000,000 properties around the world, it's easy to find a Sleepy Hollow package deal that satisfies your wanderlust.
Why should I purchase my Sleepy Hollow vacation bundle with Travelocity?
By booking your flights, hotel, car rental and activities all in the one place, you'll save both time and money. We offer round-the-clock customer support, and you'll know that you're always getting the best deal in town with our Price Match Guarantee. So, what's stopping you? Book the getaway of your dreams today and start packing!
Can I save money on my Sleepy Hollow car rental if I book it with hotels and flights?
You most certainly can — bundle your flight, hotel and car into a Sleepy Hollow vacation package and you can save a handsome sum. With so much to see and do in the Sleepy Hollow area, having your own ride will more than come in handy. Once you're in the driver's seat, crank up the tunes and make your way to Wrigley Field, an unmissable sight roughly 35 mi from Sleepy Hollow.
What is the best time of year to go to Sleepy Hollow?
You can swerve the crowds and save money in December, January and February, the quietest period for tourist visits. The high season months of May, June and August are naturally busier (and pricier), but more will be happening around Sleepy Hollow. Lock in a hotel in and get a lot more bang for your buck. Room rates tend to be highest in .
Which airport is best for Sleepy Hollow?
O'Hare Intl. Airport (ORD), located around 20 mi east of downtown Sleepy Hollow, is most likely where you'll touch down. Your other options are Midway Intl. Airport (MDW) (35 mi away from central Sleepy Hollow) and Rockford, IL (RFD-Greater Rockford) (40 mi away from central Sleepy Hollow).
Where should I stay when visiting Sleepy Hollow?
Many visitors check in to the Your BIG home away from home(KING SUITE 3QUEEN beds+)hghwy 90 to Chicago/O'Hare. It's sure to be a great base for your Sleepy Hollow vacation.

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