Sleepy Hollow Holidays from AU$2,160
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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.
Level Chicago Fulton Market
Downtown Chicago
Price was AU$2,657, price is now AU$2,160 per person
AU$2,160
per person
29 May - 1 June
found 17 hours ago
Return direct flight included
Honolulu (HNL) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great and helpful staff very clean, a place where you don’t feel out of place
Reviewed on 25 Apr 2026
L7 Chicago by LOTTE
Downtown Chicago
Price was AU$4,759, price is now AU$3,797 per person
AU$3,797
per person
27 May - 1 June
found 16 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.6/10 Exceptional! (3,950 reviews)
I had a very short stay in Chicago and had a hard time finding a hotel at a reasonable price. This
Reviewed on 26 Apr 2026
Level Chicago - River North
Downtown Chicago
Price was AU$3,120, price is now AU$2,314 per person
AU$2,314
per person
29 May - 1 June
found 17 hours ago
Return direct flight included
Honolulu (HNL) to Chicago (ORD)
9.2/10 Wonderful! (932 reviews)
Very spontaneous view! Room was very clean and kitchen is top tier.
Reviewed on 25 Apr 2026
InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
Price was AU$3,463, price is now AU$2,666 per person
AU$2,666
per person
29 May - 1 June
found 17 hours ago
Return direct flight included
Honolulu (HNL) to Chicago (ORD)
9.2/10 Wonderful! (2,975 reviews)
Amazing location, great staff, room was luxurious, doormen were super friendly and helpful!
Reviewed on 24 Apr 2026
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$83 per night from 9 May to 10 May
AU$83
9 May - 10 May
includes taxes & fees
5.4/10 (1,004 reviews)
Worst place I’ve ever seen in my life. I did NOT stay here and they won’t refund either. Would definitely advise to stay far far away.
Reviewed on 23 Apr 2026
Eaglewood Resort and Spa
1401 Nordic Rd Itasca IL
Fully refundableReserve now, pay when you stay
The price is AU$190 per night from 10 May to 11 May
AU$190
10 May - 11 May
includes taxes & fees
8.8/10 Excellent! (1,035 reviews)
very old facility with marijuna smells
Reviewed on 24 Apr 2026
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
1200 N Mittel Blvd Wood Dale IL
Fully refundableReserve now, pay when you stay
The price is AU$151 per night from 3 May to 4 May
AU$151
3 May - 4 May
includes taxes & fees
8/10 Very Good! (1,001 reviews)
Nice location and huge building, an clean room. But it is currently being renovated, so the public areas are mostly inaccessible.
Reviewed on 20 Apr 2026
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.
