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.
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Save 100% on your flight
Price was $424, price is now $258 per person
$258
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the free full breakfast each morning.
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,560, price is now $638 per person
$638
per person
Dec 23 - Dec 28
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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $682, price is now $383 per person
$383
per person
Nov 14 - Nov 17
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.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,135, price is now $670 per person
$670
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, laundry facilities, and concierge services are also on offer.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $919, price is now $562 per person
$562
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A seasonal outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free. A business center, a picnic area, and luggage storage are also on offer.

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
$98 nightly
The price is $108 total per night
$108 total
Oct 12 - Oct 13
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
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
$93 nightly
The price is $103 total per night
$103 total
Oct 30 - Oct 31
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
$122 nightly
The price is $135 total per night
$135 total
Nov 1 - Nov 2
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
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
$64 nightly
The price is $74 total per night
$74 total
Oct 19 - Oct 20
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi, free self parking, and a free area shuttle. Traveling on business? Take advantage of the 4 conference rooms, along with the 24-hour business center. There's a 24-hour gym on site, and a 24-hour front desk and a terrace are also provided.
Parking included
Free WiFi
Comfort Inn Chicago Schaumburg - O'Hare Airport

Comfort Inn Chicago Schaumburg - O'Hare Airport

2.5 out of 5
1300 E Higgins Rd, Schaumburg, IL
Free Cancellation
Reserve now, pay when you stay
$80 nightly
The price is $92 total per night
$92 total
Oct 12 - Oct 13
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and airport shuttle. Relax with a drink at the bar/lounge and enjoy free perks like full breakfast and free self parking.
Pool
Breakfast included
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 2 - Nov 3
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
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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 $258. 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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