Sleepy Hollow Vacations from ￥189,824
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The Latest Sleepy Hollow Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hilton Chicago O'Hare Airport
O'Hare
Price was ￥246,540, price is now ￥189,824 per person
￥189,824
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
It’s convenient but old features and breakfast was overpriced. Cheap and simple menus. Service person was not friendly.
Reviewed on Dec 6, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥307,991, price is now ￥211,934 per person
￥211,934
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom.
Reviewed on Dec 14, 2025
Chicago luxury home suites
Downtown Chicago
Save 100% on your flight
Price was ￥564,895, price is now ￥393,365 per person
￥393,365
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
10/10 Exceptional! (1 review)
Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job.
Reviewed on Nov 26, 2025
The Peninsula Chicago
Downtown Chicago
Price was ￥367,895, price is now ￥260,594 per person
￥260,594
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
One of the best, if not the best we have ever stayed at. Staff were exceptional including Osama who made us welcome from the moment we arrived.
Outstanding!!
Reviewed on Dec 15, 2025
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥351,432, price is now ￥249,102 per person
￥249,102
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Absolutely fantastic hotel great service, you couldn’t ask for more.
Reviewed on Dec 3, 2025
Find the Best Sleepy Hollow Vacation Packages
Sleepy Hollow Hotel Deals
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 ￥7,533 per night from Dec 30 to Dec 31
￥7,533
￥8,437 total
Dec 30 - Dec 31
includes taxes & fees
5.4/10 (1,005 reviews)
Staff was very helpful
Reviewed on Dec 16, 2025
DoubleTree by Hilton Chicago - Arlington Heights
75 W Algonquin Rd Arlington Heights IL
Fully refundableReserve now, pay when you stay
The price is ￥13,346 per night from Dec 21 to Dec 22
￥13,346
￥14,945 total
Dec 21 - Dec 22
includes taxes & fees
8/10 Very Good! (1,006 reviews)
yes
Reviewed on Dec 10, 2025
Eaglewood Resort and Spa
1401 Nordic Rd Itasca IL
Fully refundableReserve now, pay when you stay
The price is ￥15,713 per night from Dec 28 to Dec 29
￥15,713
￥20,849 total
Dec 28 - Dec 29
includes taxes & fees
8.6/10 Excellent! (1,017 reviews)
I am a big fan of the resort. I love the ambiance and amenities. And, the staff is very friendly. I will continue to make it my resort of choice when in the area!
Reviewed on Dec 15, 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.
