Highwood Vacations from ￥194,842
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 Highwood Vacation Packages
Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago O'Hare Airport - Rosemont
Price was ￥229,735, price is now ￥215,397 per person
￥215,397
per person
Apr 27 - Apr 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
8.6/10 Excellent! (1,001 reviews)
The people at the admission desk were very helpful.
Reviewed on Jan 15, 2026
Hilton Rosemont Chicago O'Hare
Price was ￥223,628, price is now ￥210,348 per person
￥210,348
per person
Apr 27 - Apr 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
Chambre très propre tour est fonctionnel et barman très gentil et professionnel
Reviewed on Jan 27, 2026
Chicago Marriott Suites O'Hare
Price was ￥249,896, price is now ￥236,550 per person
￥236,550
per person
Apr 27 - Apr 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
8.8/10 Excellent! (1,002 reviews)
Room was fine. General condition of hotel was “worn!”
Reviewed on Jan 25, 2026
Find the Best Highwood Vacation Packages
Highwood Hotel Deals
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥30,014 per night from Feb 21 to Feb 22
￥30,014
￥35,233 total
Feb 21 - Feb 22
includes taxes & fees
8.2/10 Very Good! (2,187 reviews)
Room was great and so was the service.
Reviewed on Jan 25, 2026
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
5440 N River Rd Rosemont IL
Fully refundable
The price is ￥16,847 per night from Feb 2 to Feb 3
￥16,847
￥19,201 total
Feb 2 - Feb 3
includes taxes & fees
8.6/10 Excellent! (2,717 reviews)
Staff was great. Breakfast buffet was perfect for us, and the location worked well for connecting with our flight.
Reviewed on Jan 22, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is ￥19,396 per night from Feb 9 to Feb 10
￥19,396
￥22,108 total
Feb 9 - Feb 10
includes taxes & fees
8.8/10 Excellent! (2,349 reviews)
Very courteous check-in.
Reviewed on Jan 27, 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.
Discover the most popular places to visit in Highwood
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
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
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Highwood
Chicago: Navy Pier Centennial Wheel Ticket
￥3,883
per adult
88% of travellers recommend
Chicago Crime and Mob Bus Tour
￥7,748
per adult
92% of travellers recommend
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
