Sleepy Hollow Holidays from AU$6,234
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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 – Old Town
Downtown Chicago
Price was AU$7,067, price is now AU$6,234 per person
AU$6,234
per person
2 Jan - 8 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Its room was perfect the only bad part was their was a couple stains in the bathroom wall
Reviewed on 1 Dec 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was AU$7,947, price is now AU$6,774 per person
AU$6,774
per person
2 Jan - 8 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The property was beautiful. The holiday decorations were magical. The staff was friendly and helpful.
Reviewed on 1 Dec 2025
The Emily Hotel
Downtown Chicago
Price was AU$7,246, price is now AU$6,354 per person
AU$6,354
per person
2 Jan - 8 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay.
Reviewed on 26 Nov 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
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$165 per night from 2 Jan to 3 Jan
AU$165
2 Jan - 3 Jan 2026
includes taxes & fees
8/10 Very Good! (1,032 reviews)
Room spotless. Staff just perfect.
Reviewed on 23 Nov 2025
Comfort Inn & Suites Arlington Heights - Schaumburg
2112 S Arlington Heights Rd Arlington Heights IL
The price is AU$96 per night from 21 Dec to 22 Dec
AU$96
21 Dec - 22 Dec
includes taxes & fees
8.2/10 Very Good! (829 reviews)
Clean room great stay
Reviewed on 30 Nov 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$147 per night from 21 Dec to 22 Dec
AU$147
21 Dec - 22 Dec
includes taxes & fees
8/10 Very Good! (1,011 reviews)
Front desk staff was wonderful, room was spotless. Though, we did think they had a 24 hour airport shuttle, but that may have been our mistake.
Reviewed on 22 Nov 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.
