Sleepy Hollow Vacations from ￥162,089
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The Latest Sleepy Hollow Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Staybridge Suites Chicago O'Hare - Rosemont by IHG
O'Hare
Price was ￥205,146, price is now ￥162,089 per person
￥162,089
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,007 reviews)
Very nice place lots of room for everyone great location
Reviewed on Aug 30, 2025
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was ￥403,008, price is now ￥280,014 per person
￥280,014
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,100 reviews)
Friendly and helpful staff
Reviewed on Sep 3, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥217,789, price is now ￥162,314 per person
￥162,314
per person
Dec 1 - Dec 3
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,342 reviews)
Have stay at multiple Riu hotel in my many travel. Always a great value. Their breakfast is exceptional and the service is always above average.
Reviewed on Sep 4, 2025
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was ￥223,582, price is now ￥175,292 per person
￥175,292
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.
Reviewed on Aug 21, 2025
Cambria Hotel Chicago Loop - Theatre District
Downtown Chicago
Price was ￥346,860, price is now ￥278,390 per person
￥278,390
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,390 reviews)
It's close to everything you need to be close to.
Reviewed on Sep 2, 2025
Find the Best Sleepy Hollow Vacation Packages
Sleepy Hollow Hotel Deals
Wyndham Garden Schaumburg Chicago Northwest
1725 E Algonquin Road, Schaumburg, IL
Fully refundableReserve now, pay when you stay
The price is ￥8,603 per night from Sep 15 to Sep 16
￥8,603
￥9,892 total
Sep 15 - Sep 16
includes taxes & fees
Hyatt Regency Schaumburg Chicago
1800 East Golf Rd, Schaumburg, IL
Fully refundableReserve now, pay when you stay
The price is ￥29,462 per night from Sep 7 to Sep 8
￥29,462
￥33,874 total
Sep 7 - Sep 8
includes taxes & fees
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 ￥14,447 per night from Sep 15 to Sep 16
￥14,447
￥16,033 total
Sep 15 - Sep 16
includes taxes & fees
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.