
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.


La Banque Hotel
Price was CA $1,406, price is now CA $853 per person
CA $853
per person
Apr 23 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.
Reviewed on Jan 26, 2026

Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,444, price is now CA $1,542 per person
CA $1,542
per person
May 4 - May 9
found 16 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Room smelled like food but overall very clean, very great service and staff both night and morning shift.
Reviewed on Feb 16, 2026

Park Hyatt Chicago
Downtown Chicago
Price was CA $2,521, price is now CA $1,811 per person
CA $1,811
per person
Apr 23 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
The staff were lovely. As it was our anniversary, we were given a beautiful room overlooking the water tower and the lake. The room was exceptional - the bath tub, huge! The hotel itself was within walking distance to almost everywhere - the lake, the river, the magnificent mile. There were cafes and restaurants very close by. We had a fantastic time in Chicago because of this!
Reviewed on Feb 20, 2026

4BR Corporate Suite Central and Modern
Near North Side
Price was CA $2,119, price is now CA $1,562 per person
CA $1,562
per person
Apr 23 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
10/10 Exceptional! (8 reviews)
Our stay at Envitae was amazinggg!! I’m so glad I booked with them for my Chicago trip with my family. The place was so nice and clean and decorated nicely and looks exactly like the pictures! This place literally had everything we needed and was so accommodating from having soap and shampoo to pots and pans pretty anything you could think of that you may need they had stocked. Also they were checking in with us to make sure our stay was going well they even were so kind to send us gourmet doughnuts!! The views were amazing and the location was literally near everything you could think of in walking distance. I would definitely book here again! Thank you so much for having us!
Reviewed on Jan 30, 2026
Sleepy Hollow Hotel Deals

Comfort Inn & Suites Arlington Heights - Schaumburg
2112 S Arlington Heights Rd Arlington Heights IL
The price is CA $104 per night from Mar 3 to Mar 4
CA $104
CA $116 total
Mar 3 - Mar 4
includes taxes & fees
8.2/10 Very Good! (1,036 reviews)
Do not stay there! Rooms are neglected. Bedding had 4 blood stains... I was moved to another room. In the new room the bathroom was in poor shape, wallpaper coming off, hair dryer never worked, tub faucet dripping water and making noises all night, toilet loose and about to fall off! Carpet dirty! ...
Reviewed on Feb 26, 2026

Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts
22 West Algonquin Road Arlington Heights IL
Fully refundableReserve now, pay when you stay
The price is CA $72 per night from Mar 6 to Mar 7
CA $72
CA $81 total
Mar 6 - Mar 7
includes taxes & fees
5.6/10 (1,002 reviews)
Room was very small. TV was going bad with dark screen hard to see. King-size bed was comfortable. Room was clean. Staff was fine. No coffee maker. No iron or ironing board.
Reviewed on Feb 25, 2026

Country Inn & Suites by Radisson, Elk Grove Village/Itasca
1160 W Devon Avenue Elk Grove Village IL
Fully refundable
The price is CA $132 per night from Mar 22 to Mar 23
CA $132
CA $149 total
Mar 22 - Mar 23
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
Perfect place to stay Good breakfast options Clean rooms
Reviewed on Feb 26, 2026
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.








