Sleepy Hollow Holidays from AU$808

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$703 when you book a flight and hotel together*

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

    Rest easy

    Plan, book, and manage your trip all in one place

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 Drake
Park Hyatt Chicago
Trump International Hotel & Tower Chicago
Swissotel - Chicago
Pendry Chicago

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

Courtyard by Marriott Chicago Wood Dale

Courtyard by Marriott Chicago Wood Dale

3 out of 5
900 N Wood Dale Rd, Wood Dale, IL
Fully refundableReserve now, pay when you stay
The price is AU$158 per night from 30 Oct to 31 Oct
AU$158
30 Oct - 31 Oct
includes taxes & fees
8.4/10 Very Good! (1,006 reviews)
"Great place."

Reviewed on 9 Oct 2025

Courtyard by Marriott Chicago Wood Dale
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
Fully refundableReserve now, pay when you stay
The price is AU$166 per night from 26 Oct to 27 Oct
AU$166
26 Oct - 27 Oct
includes taxes & fees
8/10 Very Good! (1,025 reviews)
"Very cool place"

Reviewed on 13 Oct 2025

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
Wyndham Garden Schaumburg Chicago Northwest

Wyndham Garden Schaumburg Chicago Northwest

3 out of 5
1725 E Algonquin Road, Schaumburg, IL
Fully refundableReserve now, pay when you stay
The price is AU$107 per night from 29 Oct to 30 Oct
AU$107
29 Oct - 30 Oct
includes taxes & fees
6.6/10 (1,029 reviews)
"The venue was nice, a bit far from the Chicago Marathon start, but it was a good place to rest. Fitness room was nice with cable weights and treadmills as well."

Reviewed on 13 Oct 2025

Wyndham Garden Schaumburg Chicago Northwest
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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.