
Highland Hills Vacations from ¥354,482
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ¥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Highland Hills Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥430,486, price is now ¥354,482 per person
¥354,482
per person
May 13 - May 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Great breakfast. Comfortable beds. Rooftop bar was not open. The resort fee at check in was a surprise. A great location and nice place.
Reviewed on Apr 1, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥454,488, price is now ¥361,036 per person
¥361,036
per person
May 1 - May 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Comfortable, clean room, and you can't beat the view! My favorite thing is relaxing on the chaise lounge, watching the sun rise over Lake Michigan! The food at Lirica is awesome, too.
Reviewed on Apr 1, 2026

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥491,402, price is now ¥394,486 per person
¥394,486
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,646 reviews)
My husband and I stayed in the presidential suite. It was absolutely spectacular. Wonderful food at prime Ocean and good breakfast. Amenities were out of this world. Customer service was amazing. We met the best bartender ever at the rooftop bar. The views were the best in Chicago!! highly recommend this hotel.
Reviewed on Mar 31, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥512,798, price is now ¥416,836 per person
¥416,836
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
The staff were great. Amenities were also wonderful. Will come back.
Reviewed on Mar 31, 2026
Where to stay in Highland Hills
Find the best Highland Hills areas and neighborhoods for the activities you enjoy most. Learn more about Highland Hills

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.
Highland Hills Hotel Deals

SureStay Plus Hotel by Best Western Chicago Lombard
222 E 22nd Street Lombard IL
Fully refundableReserve now, pay when you stay
The price is ¥12,141 per night from Apr 2 to Apr 3
¥12,141
¥13,474 total
Apr 2 - Apr 3
includes taxes & fees
9/10 Wonderful! (2,658 reviews)
Ernesto was fantastic simply because of his professionalism and attention to detail.
Reviewed on Apr 1, 2026

Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥39,524 per night from Apr 4 to Apr 5
¥39,524
¥46,399 total
Apr 4 - Apr 5
includes taxes & fees
8.4/10 Very Good! (2,242 reviews)
The hotel environment is very nice. Clean room,friendly staff
Reviewed on Apr 1, 2026

Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
The price is ¥21,452 per night from Apr 4 to Apr 5
¥21,452
¥24,452 total
Apr 4 - Apr 5
includes taxes & fees
8.8/10 Excellent! (2,446 reviews)
Love the bed and the room
Reviewed on Mar 29, 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.
Frequently asked questions
Discover the most popular places to visit in Highland Hills

Wrigley Field
4.5/5(2,149 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Naval Base Great Lakes
4.5/5(461 reviews)
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Navy Pier
4.5/5(4,923 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do

Chicago: Navy Pier Centennial Wheel Ticket
¥3,897
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.






