Sleepy Hollow Holidays from AU$600
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Your Sleepy Hollow Holiday
History, cuisine, art and more … There's so much to discover with a Sleepy Hollow holiday package. And with the ability to customise your city getaway, you know it'll be one that's hard to forget. Ready to explore your surroundings? Grand Victoria Casino, Santas Village and NOW Arena are just a few of the top-rated places to visit during a trip to Sleepy Hollow. Whoever you're heading away with and whatever your budget, your ultimate Sleepy Hollow holiday is just a few clicks away with Expedia.
The Latest Sleepy Hollow Holiday Deals
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
Save 100% on your flight
Price was AU$1,000, price is now AU$600 per person
AU$600
per person
9 Feb - 15 Feb
found 17 hours ago
Return flight included
New York (NYC) to Chicago (ORD)
9.2/10 Wonderful! (2,241 reviews)
Everyone was great. A special shout out to Tareka and Nate who worked behind the bar!
Reviewed on 16 Dec 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was AU$2,949, price is now AU$1,659 per person
AU$1,659
per person
9 Feb - 15 Feb
found 17 hours ago
Return flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom.
Reviewed on 14 Dec 2025
theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was AU$1,159, price is now AU$672 per person
AU$672
per person
9 Feb - 15 Feb
found 17 hours ago
Return flight included
New York (NYC) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff.
Reviewed on 8 Dec 2025
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was AU$1,413, price is now AU$827 per person
AU$827
per person
9 Feb - 15 Feb
found 17 hours ago
Return flight included
New York (NYC) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Great location, clean room and friendly staff!
Reviewed on 14 Dec 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was AU$1,935, price is now AU$1,172 per person
AU$1,172
per person
9 Feb - 15 Feb
found 17 hours ago
Return flight included
New York (NYC) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was nice. Service was good.
Reviewed on 17 Dec 2025
Sleepy Hollow Holiday
Sleepy Hollow Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Population | 3,300 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 27ºC |
Top Sights | Santas Village, Hemmens Cultural Centre and Main Beach |
Our pick of the best Sleepy Hollow Hotel Deals
Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts
22 West Algonquin Road Arlington Heights IL
Fully refundableReserve now, pay when you stay
The price is AU$82 per night from 31 Dec to 1 Jan
AU$82
31 Dec - 1 Jan 2026
includes taxes & fees
5.4/10 (1,004 reviews)
Good
Reviewed on 9 Dec 2025
DoubleTree by Hilton Chicago - Arlington Heights
75 W Algonquin Rd Arlington Heights IL
Fully refundableReserve now, pay when you stay
The price is AU$148 per night from 22 Dec to 23 Dec
AU$148
22 Dec - 23 Dec
includes taxes & fees
8/10 Very Good! (1,006 reviews)
yes
Reviewed on 10 Dec 2025
Eaglewood Resort and Spa
1401 Nordic Rd Itasca IL
Fully refundableReserve now, pay when you stay
The price is AU$217 per night from 24 Dec to 25 Dec
AU$217
24 Dec - 25 Dec
includes taxes & fees
8.6/10 Excellent! (1,017 reviews)
I am a big fan of the resort. I love the ambiance and amenities. And, the staff is very friendly. I will continue to make it my resort of choice when in the area!
Reviewed on 15 Dec 2025
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
