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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,060, price is now $648 per person
$648
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the business center, express check-in, and valet parking. A restaurant, a 24-hour front desk, and laundry facilities are also provided.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,832, price is now $983 per person
$983
per person
Oct 15 - Oct 20
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, a business center, and a picnic area are also offered.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,168, price is now $1,224 per person
$1,224
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A restaurant and a 24-hour gym are featured at this hotel. 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.
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,599, price is now $976 per person
$976
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a terrace, and a snack bar/deli are also offered.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,639, price is now $1,063 per person
$1,063
per person
Nov 1 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.

Top Sleepy Hollow hotels deals

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
The price is $148 total per night
$148 total
per night
Aug 31 - Sep 1
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.
Pool
Hot Tub
Quality Inn Schaumburg - Chicago near the Mall

Quality Inn Schaumburg - Chicago near the Mall

2.5 out of 5
600 North Martingale Rd Schaumburg IL
Free Cancellation
The price is $106 total per night
$106 total
per night
Sep 10 - Sep 11
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 hot tub and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
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
The price is $126 total per night
$126 total
per night
Sep 6 - Sep 7
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
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
The price is $118 total per night
$118 total
per night
Sep 6 - Sep 7
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like free self parking.
Pool
Free airport shuttle
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
The price is $114 total per night
$114 total
per night
Sep 11 - Sep 12
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
The price is $177 total per night
$177 total
per night
Sep 7 - Sep 8
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.
Pool
Hot Tub
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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 $648. 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.

Photos of local treasures

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