Sleepy Hollow Vacation Packages
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- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith 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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $720, price is now CA $555 per person
CA $555
per person
Sep 7 - Sep 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,767 reviews)
Terrible attitude of the front desk clerk.
Room smelled bad, dirty carpet.
Reviewed on Jun 24, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $3,614, price is now CA $2,421 per person
CA $2,421
per person
Sep 12 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (493 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026
The Talbott, Autograph Collection
Downtown Chicago
Price was CA $1,313, price is now CA $936 per person
CA $936
per person
Aug 30 - Sep 3
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (120 reviews)
Always a pleasure and a great location
Reviewed on Jun 24, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $2,819, price is now CA $2,098 per person
CA $2,098
per person
Aug 14 - Aug 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,034 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.
Reviewed on Jun 19, 2026
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 CA $156 per night from Jul 5 to Jul 6
CA $156
CA $173 total
Jul 5 - Jul 6
includes taxes & fees
7.8/10 Good! (1,006 reviews)
"Staff ck in was not what I expected from Double Tree personnel, short, seemed bothered by questions, "had some where else to be". Called front desk multiple times for a question no answer 10pm or call back (NO USB outlets!) and I forgot my adapter. Room was clean, nicely refurbished, but noisy AC, ..."
Reviewed on Jun 24, 2026
Sheraton Suites Chicago Elk Grove
121 Northwest Point Boulevard Elk Grove Village IL
Fully refundableReserve now, pay when you stay
The price is CA $120 per night from Jul 6 to Jul 7
CA $120
CA $136 total
Jul 6 - Jul 7
includes taxes & fees
8/10 Very good! (1,003 reviews)
"The pics and the actual room are misleading"
Reviewed on Jun 24, 2026
Hyatt Place Itasca
1150 North Arlington Heights Road Itasca IL
Fully refundableReserve now, pay when you stay
The price is CA $156 per night from Jun 28 to Jun 29
CA $156
CA $173 total
Jun 28 - Jun 29
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.
