Sleepy Hollow Vacations from ￥376,196
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The Latest Sleepy Hollow Vacation Packages
Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago O'Hare Airport - Rosemont
Price was ￥411,655, price is now ￥376,196 per person
￥376,196
per person
Jun 5 - Jun 11
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
8.6/10 Excellent! (1,006 reviews)
Clean king size bed but the full double beds I had at first had an a/c problem
Reviewed on Apr 16, 2026
Club Quarters Hotel Wacker at Michigan, Chicago
Downtown Chicago
Price was ￥509,183, price is now ￥424,518 per person
￥424,518
per person
Jun 5 - Jun 11
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
8.8/10 Excellent! (2,141 reviews)
Perfectly located. The staff was amazing. Room was clean. Will stay again
Reviewed on Apr 16, 2026
Claridge House Chicago, Tapestry Collection by Hilton
Downtown Chicago
Price was ￥490,324, price is now ￥422,500 per person
￥422,500
per person
Jun 5 - Jun 11
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
9/10 Wonderful! (1,520 reviews)
This is our favorite hotel in Chicago. The only thing that was different on our last trip was the parking garage next door. It is under new ownership, and they made it very difficult to leave and come back, even though we bought a three-day pass with in-and-out privileges. The management at Claridge House is aware of the situation and is working on a solution.
Reviewed on Apr 12, 2026
Find the Best Sleepy Hollow Vacation Packages
Sleepy Hollow Hotel Deals
Comfort Inn & Suites Arlington Heights - Schaumburg
2112 S Arlington Heights Rd Arlington Heights IL
The price is ￥17,082 per night from Apr 29 to Apr 30
￥17,082
￥19,128 total
Apr 29 - Apr 30
includes taxes & fees
8.2/10 Very Good! (1,111 reviews)
This place was so good
Reviewed on Apr 16, 2026
Quality Inn Schaumburg - Chicago near the Mall
600 North Martingale Rd Schaumburg IL
Fully refundableReserve now, pay when you stay
The price is ￥14,065 per night from May 6 to May 7
￥14,065
￥16,171 total
May 6 - May 7
includes taxes & fees
8.6/10 Excellent! (1,019 reviews)
Everything was great but couldn’t stand smell had to get an air freshener plug in. Great hot tub and pool area
Reviewed on Apr 14, 2026
Eaglewood Resort and Spa
1401 Nordic Rd Itasca IL
Fully refundableReserve now, pay when you stay
The price is ￥16,348 per night from May 3 to May 4
￥16,348
￥21,638 total
May 3 - May 4
includes taxes & fees
8.8/10 Excellent! (1,034 reviews)
I expected the resort to look better than what we saw on arrival. Staff professional. We were disappointed in the room upon entering. The carpet was old, patio was not well kept, the view was not a good view of the golf course (south elevator room 903) and when I went to take a shower I saw dried ...
Reviewed on Apr 14, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
