
Oak Hill Vacations from ¥256,566
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The Latest Oak Hill Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ¥367,940, price is now ¥256,566 per person
¥256,566
per person
Oct 8 - Oct 13
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,096 reviews)
I booked a king room, & was asked about upgrading to a king room on the top floor with a city view for a small fee. I agreed, and upon going to our new room we quickly found out the toilet would not flush. We went back down (maybe 30mins after we checked in) to inform them of the issue, & were told no one could fix it so we were downgraded to a queen room (not offered our original king booking). other than this, the facility was nice/clean enough and the staff was great. Still very close to shopping but was one of the quietest streets i’ve stayed on in chicago.
Reviewed on Aug 30, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was ¥474,716, price is now ¥324,740 per person
¥324,740
per person
Oct 8 - Oct 13
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
Our room is perfect to the view that we booked. The room is very spacious and clean.
Reviewed on Sep 2, 2025

Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was ¥402,756, price is now ¥276,764 per person
¥276,764
per person
Oct 8 - Oct 13
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (3,067 reviews)
This property is amazing. James and Christian were absolutely incredible!!
Reviewed on Sep 1, 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 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,100 reviews)
Enjoyed our stay at this hotel!
Reviewed on Sep 2, 2025

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was ¥369,584, price is now ¥257,358 per person
¥257,358
per person
Oct 8 - Oct 13
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,975 reviews)
Decent property, very small rooms but clean
Reviewed on Sep 2, 2025
Find the Best Oak Hill Vacation Packages
Oak Hill Hotel Deals

The Ingleside Hotel
2810 Golf Road, Pewaukee, WI
Fully refundableReserve now, pay when you stay
The price is ¥15,763 per night from Sep 4 to Sep 5
¥15,763
¥17,813 total
Sep 4 - Sep 5
includes taxes & fees

Best Western Waukesha Grand
2840 N Grandview Boulevard, Pewaukee, WI
Fully refundableReserve now, pay when you stay
The price is ¥11,645 per night from Sep 9 to Sep 10
¥11,645
¥13,159 total
Sep 9 - Sep 10
includes taxes & fees

AmericInn by Wyndham Delafield-Waukesha-Milwaukee
2412 Milwaukee St, Delafield, WI
Fully refundableReserve now, pay when you stay
The price is ¥12,952 per night from Sep 18 to Sep 19
¥12,952
¥14,635 total
Sep 18 - Sep 19
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.