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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $420, price is now $260 per person
$260
per person
Mar 27 - Mar 29
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 smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking. Limo/town car service, WiFi in public areas, and express check-out are also on offer.
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 $797, price is now $450 per person
$450
per person
Mar 19 - Mar 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,708, price is now $982 per person
$982
per person
Mar 12 - Mar 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the indoor pool and perks like a free area shuttle.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $476, price is now $278 per person
$278
per person
Mar 27 - Mar 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $539, price is now $328 per person
$328
per person
Mar 27 - Mar 29
found 1 day 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.

Top Sleepy Hollow hotels deals

Comfort Inn & Suites Arlington Heights - Schaumburg

Comfort Inn & Suites Arlington Heights - Schaumburg

3 out of 5
2112 S Arlington Heights Rd Arlington Heights IL
$76 nightly
The price is $85 total per night
$85 total
Jan 18 - Jan 19
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.
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
$125 nightly
The price is $139 total per night
$139 total
Jan 19 - Jan 20
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.
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
Reserve now, pay when you stay
$38 nightly
The price is $43 total per night
$43 total
Jan 19 - Jan 20
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.
Comfort Inn & Suites Arlington Heights - Buffalo Grove

Comfort Inn & Suites Arlington Heights - Buffalo Grove

2.5 out of 5
3700 N Wilke Rd Arlington Heights IL
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $85 total per night
$85 total
Jan 23 - Jan 24
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A 24-hour business center, a coffee shop, and a snack bar/deli are also on offer.
Country Inn & Suites by Radisson, Schaumburg, IL

Country Inn & Suites by Radisson, Schaumburg, IL

3 out of 5
1401 North Roselle Road Schaumburg IL
Free Cancellation
$98 nightly
The price is $112 total per night
$112 total
Feb 8 - Feb 9
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts

Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts

2 out of 5
22 West Algonquin Road Arlington Heights IL
Free Cancellation
Reserve now, pay when you stay
$49 nightly
The price is $54 total per night
$54 total
Jan 22 - Jan 23
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. There's luggage storage and multilingual staff can provide around-the-clock assistance.
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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 $260. 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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