Sleepy Hollow Vacation Packages
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Top Holiday Package Deals in Sleepy Hollow
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,113, price is now CA $1,436 per person
CA $1,436
per person
Aug 24 - Aug 28
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place.
Reviewed on Jul 14, 2026
Omni Chicago Hotel
Downtown Chicago
Price was CA $1,871, price is now CA $1,286 per person
CA $1,286
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
Great stay downtown. Great location. Staff was friendly and helpful.
Reviewed on Jul 14, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,089, price is now CA $1,466 per person
CA $1,466
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Very clean nice workers and amazing views
Reviewed on Jul 14, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,546, price is now CA $1,103 per person
CA $1,103
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
We booked a two bedroom unit, but the unit clearly wasn't intended for a 2 bedroom. It was obviously a sitting area or something with a bed squeezed in. There was no vent so it made it impossible to shut the door, but then it was open to the living space and a full wall of windows.
In addition, they list housekeeping as an amenity, and advertise one day or long term stays, however, for our 4 night stay, this didn't get housekeeping services. Meaning we had to get towels and coffee each day from the front desk, had piles of trash from cooking and such, and a heap of dirty towels from the week.
Staff was friendly, but not really provided agency or capacity to do anything to fix the experience. Even a request for a fan to try to cool the space was impossible for them to solve (although they certainly had one for the front desk to keep staff comfortable).
Reviewed on Jul 14, 2026
Where to stay in Sleepy Hollow
Find the best Sleepy Hollow areas and neighborhoods for the activities you enjoy most. Learn more about Sleepy Hollow
Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Sleepy Hollow Hotel Deals
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $239 per night from Aug 3 to Aug 4
CA $239
CA $273 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (2,844 reviews)
"This is the third time we’ve stayed, and every time we’ve enjoyed, property is well kept, nice rooms, great staff, wonderful breakfast, would definitely recommend!"
Reviewed on Jul 14, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $232 per night from Jul 27 to Jul 28
CA $232
CA $276 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very good! (1,747 reviews)
"We decided to extend our stay and the staff were amazing. Very courteous !!!"
Reviewed on Jul 13, 2026
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $333 per night from Jul 26 to Jul 27
CA $333
CA $443 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (1,908 reviews)
"Great stay downtown. Great location. Staff was friendly and helpful."
Reviewed on Jul 14, 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.
Frequently asked questions
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
CA $35
per adult
88% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $64
per adult
94% of travellers recommend
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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.