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.
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination
Price was CA $1,084, price is now CA $784 per person
CA $784
per person
Sep 11 - Sep 14
found 5 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.6/10 Excellent! (1,024 reviews)
Clean large room. Friendly helpful staff. Garage parking with covered bridge to hotel and casino. Highly recommend.
Reviewed on Jun 25, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $3,635, price is now CA $2,437 per person
CA $2,437
per person
Sep 12 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well
Reviewed on Jun 26, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,544, price is now CA $1,096 per person
CA $1,096
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,767 reviews)
Our room this time was more cozy (re: small). Bathroom was efficient (re: cramped). I would guess they took a suite and made an extra room of it. Staff was great, hotel clean. Just a bad draw in the room - we arrived late.
Reviewed on Jun 27, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,991, price is now CA $2,125 per person
CA $2,125
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!
Reviewed on Jun 25, 2026
Sleepy Hollow Hotel Deals
Sheraton Suites Chicago Elk Grove
121 Northwest Point Boulevard Elk Grove Village IL
Fully refundableReserve now, pay when you stay
The price is CA $130 per night from Jul 9 to Jul 10
CA $130
CA $147 total
Jul 9 - Jul 10
includes taxes & fees
8/10 Very good! (1,006 reviews)
"Clean comfortable quiet & great location"
Reviewed on Jun 27, 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 Jul 26 to Jul 27
CA $156
CA $173 total
Jul 26 - Jul 27
includes taxes & fees
8.8/10 Excellent! (1,169 reviews)
"Good"
Reviewed on Jun 27, 2026
The Westin Chicago Northwest
400 Park Blvd Itasca IL
Fully refundableReserve now, pay when you stay
The price is CA $212 per night from Jul 5 to Jul 6
CA $212
CA $236 total
Jul 5 - Jul 6
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"Staff is friendly. The rooms were clean with comfortable beds."
Reviewed on Jun 21, 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.
