Sleepy Hollow Holidays
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Top Flight + Hotel Deals in Sleepy Hollow
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,505, price is now €1,005 per person
€1,005
per person
1 Feb - 6 Feb
found 24 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
18.8/10 Exceptional! (1,773 reviews)
Political stigma aside, I must say, this property is stunning across the board. From the moment you enter the building you're met with this amazingly inviting fragrance.
The Room was spotless. All the staff was sincere, kind, hospitable, and surprisingly diverse. Also, The front desk was exceptionally accommodating while I (minimally) "stress tested" the room service. 10/10 would and Will return.
Mr. & Mrs.S
Reviewed on 17 Nov 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was €952, price is now €662 per person
€662
per person
1 Feb - 6 Feb
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
18.4/10 Exceptional! (317 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.
Reviewed on 28 Oct 2025
Pendry Chicago
Downtown Chicago
Price was €937, price is now €670 per person
€670
per person
1 Feb - 6 Feb
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
18.8/10 Exceptional! (1,130 reviews)
Everything was excellent. Will definitely stay here again. I really liked the scent of the bath/shower products and the candles in the lobby
Reviewed on 20 Nov 2025
Top hotels in Sleepy Hollow
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 €86 per night from 27 Nov to 28 Nov
€86
27 Nov - 28 Nov
includes taxes & fees
8/10 Very Good! (1,013 reviews)
Clean rooms Friendly front desk. Warm cookies in check in a nice touch!
Reviewed on 17 Nov 2025
Wyndham Garden Schaumburg Chicago Northwest
1725 E Algonquin Road Schaumburg IL
Fully refundableReserve now, pay when you stay
The price is €63 per night from 23 Nov to 24 Nov
€63
23 Nov - 24 Nov
includes taxes & fees
6.4/10 (1,005 reviews)
It was quiet and affort
Reviewed on 14 Nov 2025
Courtyard by Marriott Chicago Wood Dale
900 N Wood Dale Rd Wood Dale IL
Fully refundableReserve now, pay when you stay
The price is €77 per night from 28 Nov to 29 Nov
€77
28 Nov - 29 Nov
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
Comfy bed and nice bistro in the lobby
Reviewed on 15 Nov 2025
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.
