Sleepy Hollow Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
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Better together
Save up to CA $1,096 when you book a flight and hotel together*
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With over 300,000 hotels worldwide, it's easy to create a perfect package
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Your Sleepy Hollow Vacation
Entertainment, history, art and more … There's so much to experience with a Sleepy Hollow vacation package. And with the ability to customize your city getaway, it's guaranteed to be one you won't forget. Make your trip to Sleepy Hollow even more fun by going sightseeing. Grand Victoria Casino, Santas Village and NOW Arena are among the top attractions worth exploring. Whatever your travel plans or budget, organizing your ultimate tailored Sleepy Hollow vacation is simple with Expedia.
Top Sleepy Hollow Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Park Hyatt Chicago
Downtown Chicago
Price was CA $3,592, price is now CA $2,089 per person
CA $2,089
per person
Nov 17 - Nov 23
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Excellent service with great top notch amenities and a room that has everything you can need away from home. Highly recommend!
Reviewed on Aug. 31, 2025
Arlo Chicago
Downtown Chicago
Price was CA $1,313, price is now CA $837 per person
CA $837
per person
Oct 7 - Oct 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,828 reviews)
Great staff and quality of service. Check in process a little confusing and stressful at first but location, amenities, and friendly team made our experience memorable.
Reviewed on Sep. 2, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,906, price is now CA $1,221 per person
CA $1,221
per person
Oct 7 - Oct 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
Best, very clean, best view, really enjoyed the stay!
Reviewed on Sep. 2, 2025
Sleepy Hollow Hotel Deals
Wyndham Garden Schaumburg Chicago Northwest
1725 E Algonquin Road, Schaumburg, IL
Fully refundableReserve now, pay when you stay
The price is CA $93 per night from Sep 11 to Sep 12
CA $93
CA $107 total
Sep 11 - Sep 12
includes taxes & fees
Hyatt Regency Schaumburg Chicago
1800 East Golf Rd, Schaumburg, IL
Fully refundableReserve now, pay when you stay
The price is CA $233 per night from Sep 4 to Sep 5
CA $233
CA $268 total
Sep 4 - Sep 5
includes taxes & fees
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 CA $133 per night from Sep 17 to Sep 18
CA $133
CA $148 total
Sep 17 - Sep 18
includes taxes & fees
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.