Sleepy Hollow Vacations from ￥227,504
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The Latest Sleepy Hollow Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥278,740, price is now ￥227,504 per person
￥227,504
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Very pleased with our stay. From the beginning to the end, the customer service was amazing. Room very clean and modern as well as the bathroom. You can definitely walk around and there are quite a few of dining options. Breakfast was amazing. Great quality for a free buffet. Will definitely return.
Reviewed on Oct 25, 2025
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥337,495, price is now ￥276,901 per person
￥276,901
per person
Jan 18 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
We had a devastating family emergency and the staff handled everything for us. They were so kind and compassionate. I don’t know how I could have handled getting to the airport and returning the rental car without them.
Reviewed on Oct 23, 2025
Park Hyatt Chicago
Downtown Chicago
Price was ￥314,167, price is now ￥266,530 per person
￥266,530
per person
Jan 18 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend!
Reviewed on Oct 20, 2025
Level Chicago – Old Town
Downtown Chicago
Price was ￥264,586, price is now ￥228,248 per person
￥228,248
per person
Jan 18 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
We booked a two-bedroom corner suite which was very spacious (especially the kitchen/living room area), and we had very good view of the old town overlooking from the big porch. The location of the hotel was pretty nice, only 15 min to Michigan Avenue.
However, a few things were disappointing: 1) The check-in process was longer than expected which took 15-20 min to get the room keys; 2) The floor of the suite was quite dusty and the door of the master bedroom was broken (could not be locked); 3) The room phone didn't work at all and we had to use our phone to call the hotel front desk to ask questions; 4) This was the one and only hotel we'd stayed worldwide that did not provide foam pillows (feather pillows only to which one of our family members was allergic).
Reviewed on Oct 22, 2025
Where to stay in Sleepy Hollow
Find the best Sleepy Hollow areas and neighborhoods for the activities you enjoy most. Learn more about Sleepy Hollow
Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Sleepy Hollow Hotel Deals
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥19,360 per night from Nov 16 to Nov 17
￥19,360
￥22,727 total
Nov 16 - Nov 17
includes taxes & fees
8.4/10 Very Good! (5,142 reviews)
Nice
Reviewed on Oct 24, 2025
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥14,342 per night from Nov 24 to Nov 25
￥14,342
￥16,837 total
Nov 24 - Nov 25
includes taxes & fees
7.8/10 Good! (9,592 reviews)
From the moment we walked in the security was very friendly and helpful the first front desk attendant was amazing her name was Jasmine she was incredibly sweet helped us the best she could when we came back to do an early check-in the second person who helped us was incredibly rude service was terrible ...
Reviewed on Oct 26, 2025
Freehand Chicago
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥10,285 per night from Nov 26 to Nov 27
￥10,285
￥14,765 total
Nov 26 - Nov 27
includes taxes & fees
7.8/10 Good! (2,524 reviews)
Everything was great
Reviewed on Oct 24, 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.
Frequently asked questions
Discover the most popular places to visit in Sleepy Hollow
Wrigley Field
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
4.5/5(332 reviews)
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Navy Pier
4.5/5(4,870 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Skydeck - Willis Tower Admission
￥6,612
per adult
100% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
￥3,691
per adult
84% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.