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 $2,197, price is now CA $1,334 per person
CA $1,334
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) 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
Hyatt Centric Chicago Magnificent Mile
Downtown Chicago
Price was CA $2,153, price is now CA $1,389 per person
CA $1,389
per person
Oct 24 - Oct 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,028 reviews)
It was great for a short stay with my family. We enjoyed the location and proximity to public transportation.
Reviewed on Sep. 4, 2025
The Langham, Chicago
Downtown Chicago
Price was CA $2,322, price is now CA $1,512 per person
CA $1,512
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug. 12, 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 $75 per night from Oct 3 to Oct 4
CA $75
CA $86 total
Oct 3 - Oct 4
includes taxes & fees
Hyatt Regency Schaumburg Chicago
1800 East Golf Rd, Schaumburg, IL
The price is CA $275 per night from Sep 7 to Sep 8
CA $275
CA $316 total
Sep 7 - Sep 8
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 $135 per night from Sep 14 to Sep 15
CA $135
CA $150 total
Sep 14 - Sep 15
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.
