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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was $1,061, price is now $758 per person
$758
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A lobby fireplace, a communal living room, and express check-out are also on offer.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,555, price is now $945 per person
$945
per person
Sep 24 - Sep 29
found 16 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,445, price is now $959 per person
$959
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,514, price is now $1,022 per person
$1,022
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, a business center, and a picnic area are also offered.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,337, price is now $943 per person
$943
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
This hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Self parking, a coffee shop, and a terrace are also offered.

Top Sleepy Hollow hotels deals

Sheraton Suites Chicago Elk Grove

Sheraton Suites Chicago Elk Grove

3.5 out of 5
121 Northwest Point Boulevard Elk Grove Village IL
$116 nightly
The price is $131 total per night
$131 total
Jul 19 - Jul 20
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 free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
DoubleTree by Hilton Chicago - Arlington Heights

DoubleTree by Hilton Chicago - Arlington Heights

4 out of 5
75 W Algonquin Rd Arlington Heights IL
Free Cancellation
Reserve now, pay when you stay
$106 nightly
The price is $118 total per night
$118 total
Aug 9 - Aug 10
Total with taxes and fees
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 perks like free self parking.
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
$147 nightly
The price is $164 total per night
$164 total
Aug 9 - Aug 10
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 indoor pool and 24-hour gym, and relax with drinks at one of the 2 bars/lounges.
Hyatt Place Itasca

Hyatt Place Itasca

3 out of 5
1150 North Arlington Heights Road Itasca IL
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $122 total per night
$122 total
Jul 26 - Jul 27
Total with taxes and fees
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 perks like buffet breakfast and free self parking.
Pool
Breakfast included
The Westin Chicago Northwest

The Westin Chicago Northwest

4 out of 5
400 Park Blvd Itasca IL
Free Cancellation
Reserve now, pay when you stay
$144 nightly
The price is $160 total per night
$160 total
Aug 14 - Aug 15
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 free WiFi in public areas. Enjoy the hot tub and perks like a free area shuttle.
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
$98 nightly
The price is $108 total per night
$108 total
Jul 26 - Jul 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
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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 $758. 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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