
Highland Vacations from ¥246,796
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The Latest Highland Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Eaglewood Resort and Spa
Price was ¥265,064, price is now ¥246,796 per person
¥246,796
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,005 reviews)
Good hotel but to bad the hot tub is not hot enough and there's an another customer also complained about that
Reviewed on Apr 8, 2026


Four Seasons Hotel Chicago
Downtown Chicago
Price was ¥456,758, price is now ¥397,960 per person
¥397,960
per person
Jun 24 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Beautiful and in walking distance to so many shops and cafes! We had a great stay.
Reviewed on Apr 6, 2026

Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
Price was ¥324,456, price is now ¥294,628 per person
¥294,628
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (5,808 reviews)
Perfect location for a family trip, the hotel amenities were amazing and the staff was very friendly.
We did have an issue with having our room serviced during our stay, after a long day out we came back to it still not being serviced, after asking the front desk they said they would put in the request so we hung out in the atrium for an hour and a half and it still wasn’t done, had to go down to the front desk again and ask which was very frustrating.
Reviewed on Apr 9, 2026
Find the Best Highland Vacation Packages
Highland Hotel Deals

Hilton Chicago/Oak Lawn
9333 S Cicero Ave Oak Lawn IL
Fully refundableReserve now, pay when you stay
The price is ¥19,438 per night from Apr 19 to Apr 20
¥19,438
¥22,349 total
Apr 19 - Apr 20
includes taxes & fees
8.4/10 Very Good! (1,273 reviews)
Parking was not free. They charged us $25 port day when it clearly started that parking was free when we booked the hotel
Reviewed on Apr 9, 2026

Wind Creek Southland Casino and Hotel
17300 S Halsted St Hazel Crest IL
Fully refundableReserve now, pay when you stay
The price is ¥28,477 per night from Apr 13 to Apr 14
¥28,477
¥31,888 total
Apr 13 - Apr 14
includes taxes & fees
9.4/10 Exceptional! (319 reviews)
overall good stay but the batteries in my tv remote were dead. house keeping should check those things while cleaning the rooms. i mentioned it so the front desk and they had them replaced but no apology for the inconvenience was issued.
Reviewed on Apr 10, 2026

EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
18501 Convention Center Drive Tinley Park IL
Fully refundable
The price is ¥16,704 per night from Apr 19 to Apr 20
¥16,704
¥19,946 total
Apr 19 - Apr 20
includes taxes & fees
9/10 Wonderful! (1,263 reviews)
My mom was unable to get breakfast although I paid for it, as I thought she'd be able to getcroom service... she needs a scooter. We took food and drinks to her room initially.
Reviewed on Apr 9, 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.

