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.
Level Chicago Fulton Market
Downtown Chicago
Price was €1,735, price is now €1,160 per person
€1,160
per person
23 Jun - 28 Jun
found 7 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great and helpful staff very clean, a place where you don’t feel out of place
Reviewed on 25 Apr 2026
Swissotel - Chicago
Downtown Chicago
Price was €2,109, price is now €1,410 per person
€1,410
per person
23 Jun - 28 Jun
found 7 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (3,280 reviews)
Corner room with breath taking view. It was my second time in this hotel, it never disappoints.
Reviewed on 27 Apr 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was €1,956, price is now €1,376 per person
€1,376
per person
23 Jun - 28 Jun
found 7 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,663 reviews)
bar selection and staff wonderful
Reviewed on 28 Apr 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was €1,853, price is now €1,310 per person
€1,310
per person
23 Jun - 28 Jun
found 7 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (2,131 reviews)
Great location, nice property, extremely slow breakfast at in house restaurant Toro. Didn’t appreciate paying an “urban experience fee” with associated taxes.
Reviewed on 24 Apr 2026
Top hotels in Sleepy Hollow
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 €51 per night from 23 May to 24 May
€51
23 May - 24 May
includes taxes & fees
5.4/10 (1,005 reviews)
Room 216 was in need of some maintenance. AC unit wasn’t working properly, some kid used a blue pen to draw on the arms of the chair, and the water pressure wasn’t very good for the toilet or the shower. Otherwise staff was friendly and facility was decent
Reviewed on 26 Apr 2026
Eaglewood Resort and Spa
1401 Nordic Rd Itasca IL
Fully refundableReserve now, pay when you stay
The price is €116 per night from 17 May to 18 May
€116
17 May - 18 May
includes taxes & fees
8.8/10 Excellent! (1,044 reviews)
This resort was just ok imo. Pretty old and dated. Not the worst place I’ve been but needs work. Carpet old , old scratched up furnishings in the rooms. ATP no hotel should have a tub only glassed in showers. Didn’t use the amenities like the bowling alley as it was closed when we arrived. This place ...
Reviewed on 26 Apr 2026
Comfort Inn & Suites Arlington Heights - Schaumburg
2112 S Arlington Heights Rd Arlington Heights IL
The price is €98 per night from 10 May to 11 May
€98
10 May - 11 May
includes taxes & fees
8.2/10 Very Good! (1,130 reviews)
I stayed with my family for a night and was comfortable. It was a good value for money
Reviewed on 28 Apr 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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