
Sleepy Hollow Vacation Packages
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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.

Holiday Inn & Suites Chicago - Downtown by IHG
Downtown Chicago
Price was CA $2,212, price is now CA $1,404 per person
CA $1,404
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,104 reviews)
Front desk staff
Every front desk person was friendly and helpful
Room
Spacious and Recently updated
Location
Proximity to CTA is perfect or walkable to attractions, Grant Park etc
Amenities
5 stars for on site washer dryer. First time I've ever seen this at a hotel
Reviewed on Aug 5, 2026


Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $3,677, price is now CA $2,273 per person
CA $2,273
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,770 reviews)
We enjoyed the roof top bar and the glass floor experience in the roof top bar
Room was clean and breakfast changed daily
In a good area for attractions and transport
Reviewed on Aug 5, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,858, price is now CA $1,776 per person
CA $1,776
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,606 reviews)
Our stay was amazing with a beautiful view.
Reviewed on Aug 5, 2026

Eurostars Magnificent Mile
Downtown Chicago
Price was CA $2,383, price is now CA $1,573 per person
CA $1,573
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,752 reviews)
Rating: ★★★★★
Stayed: July 31, 2026
My stay at Eurostars Magnificent Mile was excellent. The location is very convenient — the Grand train station is only about a 6‑minute walk, making it easy to get around the city and even reach Wrigley Field without any hassle. The area feels lively, safe, and perfect for exploring Chicago.
Breakfast was very good, and the staff was friendly and attentive. I want to highlight Cristina in particular — her service, kindness, and professionalism really stood out and made the experience even better.
Even though I was on a high floor, you can still hear some of the typical city noise (motorcycles, ambulances, police sirens). It’s part of being in downtown Chicago, and it didn’t take away from the overall quality of the stay.
Overall, this was a great experience from start to finish. I definitely recommend this hotel.
Reviewed on Aug 5, 2026
Sleepy Hollow Hotel Deals

Eaglewood Resort and Spa
1401 Nordic Rd Itasca IL
Fully refundableReserve now, pay when you stay
The price is CA $164 per night from Aug 23 to Aug 24
CA $164
CA $213 total
Aug 23 - Aug 24
includes taxes & fees
8.8/10 Excellent! (1,253 reviews)
"The bowling alley."
Reviewed on Aug 5, 2026

The Westin Chicago Northwest
400 Park Blvd Itasca IL
Fully refundableReserve now, pay when you stay
The price is CA $227 per night from Aug 20 to Aug 21
CA $227
CA $253 total
Aug 20 - Aug 21
includes taxes & fees
8.8/10 Excellent! (1,017 reviews)
"good"
Reviewed on Aug 5, 2026

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 $154 per night from Aug 16 to Aug 17
CA $154
CA $171 total
Aug 16 - Aug 17
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.
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.







