Sleepy Hollow Holidays from AU$808
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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 Drake
Downtown Chicago
Price was AU$1,183, price is now AU$808 per person
AU$808
per person
16 Nov - 19 Nov
found 23 hours ago
Return flight included
Greensboro (GSO) to Chicago (ORD)
8.8/10 Excellent! (1,291 reviews)
Great location and wonderful staff. Stayed with my family of four and we were able to easily get to all the wonderful sites we wanted to visit. The historic charm and lastige spaces enhanced our stay and our breakfast was superb.
Reviewed on 14 Oct 2025
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was AU$1,974, price is now AU$1,358 per person
AU$1,358
per person
16 Nov - 19 Nov
found 23 hours ago
Return flight included
Raleigh (RDU) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
The front desk staff was super friendly and helpful. After waking up at 4am to catch an early flight, we were thrilled when they had a room ready for us for early check-in.
Hyatt does a great job with room lay-outs. It was obvious that our room was recently renovated with a modern conveniences like motorized shades, a comfy window seat, hidden bar and Nespresso maker, and clean decor. Our friends were staying around the corner at the Ritz and liked our room better.
Reviewed on 14 Oct 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was AU$2,045, price is now AU$1,417 per person
AU$1,417
per person
16 Nov - 19 Nov
found 23 hours ago
Return flight included
Greensboro (GSO) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Excellent luxury atmosphere with second to none customer service. The bathroom was very nice. Although the toilet has a slight odor that was unexpected for the high quality room and hotel.
Reviewed on 15 Oct 2025
Pendry Chicago
Downtown Chicago
Price was AU$1,417, price is now AU$1,025 per person
AU$1,025
per person
16 Nov - 19 Nov
found 23 hours ago
Return flight included
Greensboro (GSO) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
I loved the hotel, however I would request an inside room next time. It was extremely noisy outside.
Reviewed on 11 Oct 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
Courtyard by Marriott Chicago Wood Dale
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
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$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
Wyndham Garden Schaumburg Chicago Northwest
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
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.
