Sleepy Hollow Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Flight + Hotel Deals in Sleepy Hollow
Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
Price was €1,715, price is now €1,286 per person
€1,286
per person
17 Jul - 24 Jul
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.4/10 Very Good! (3,921 reviews)
Great location! Has not been updated since the early 90"s..? Room smelled very old, musty; sheets like old cigarettes. Worth the price for a quick overnight.
Reviewed on 12 Jun 2026
Omni Chicago Hotel
Downtown Chicago
Save 100% on your flight
Price was €2,385, price is now €1,708 per person
€1,708
per person
17 Jul - 24 Jul
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,791 reviews)
Pro: Good gym, good room size, 676 restaurant. Con: room 1610 by the elevator is extremely noisy. Plus slow elevators. Late checkout charge, even though I'm a member. Shower pressure was like a fire hose, water everywhere.
Reviewed on 12 Jun 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was €2,373, price is now €1,791 per person
€1,791
per person
17 Jul - 24 Jul
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,535 reviews)
This is our second time staying at the sable and it was wonderful! The staff is amazing and friendly! The elevators were out and we got lost a couple times getting to our room, and every single staff member that we would run into each time was so helpful and kind in finding where we were supposed to go! One of the housekeepers even stopped what she was doing to walk us to our correct floor when she realized we were lost! She was so incredibly nice! The views are incredible, the location is incredible, and the staff is incredible! Will definitely be coming back on our next trip to Chicago/Navy Pier!
Reviewed on 11 Jun 2026
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Price was €2,020, price is now €1,528 per person
€1,528
per person
17 Jul - 24 Jul
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.4/10 Very Good! (1,966 reviews)
The staff was able to help us get a room earlier than the check-in time.
Reviewed on 9 Jun 2026
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 €117 per night from 26 Jun to 27 Jun
€117
26 Jun - 27 Jun
includes taxes & fees
7.8/10 Good! (1,025 reviews)
"Room was clean, but the most notable thing was the staff. Fantastic service."
Reviewed on 11 Jun 2026
Eaglewood Resort and Spa
1401 Nordic Rd Itasca IL
Fully refundableReserve now, pay when you stay
The price is €130 per night from 28 Jun to 29 Jun
€130
28 Jun - 29 Jun
includes taxes & fees
8.8/10 Excellent! (1,147 reviews)
"Everything"
Reviewed on 12 Jun 2026
The Westin Chicago Northwest
400 Park Blvd Itasca IL
The price is €147 per night from 2 Jul to 3 Jul
€147
2 Jul - 3 Jul
includes taxes & fees
8.8/10 Excellent! (1,022 reviews)
"The hotel is always nice whenever I stay here. My children and I usually come for a little getaway. The pool is really nice and, although it is operated by a different company, hotel guests are still able to swim for free. We also enjoyed using the basketball court and dining at the hotel restaurant, ..."
Reviewed on 12 Jun 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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
