Highwood Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$616 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
Highwood Holiday
Our pick of the best Highwood Hotel Deals
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$509 per night from 3 Apr to 4 Apr
NZ$509
3 Apr - 4 Apr
includes taxes & fees
8.4/10 Very Good! (2,239 reviews)
Everything was clean and the staff was very friendly and helpful!
Reviewed on 25 Mar 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is NZ$268 per night from 4 Apr to 5 Apr
NZ$268
4 Apr - 5 Apr
includes taxes & fees
8.8/10 Excellent! (2,438 reviews)
Our stay was wonderful and the manager is who checked us in, he was extremely helpful and kind. I will say just for those inquiring, the beds are very firm so if you need a soft mattress, I’d avoid this hotel. (We stayed in a room with two beds, maybe the king is different?) The breakfast buffet ...
Reviewed on 28 Mar 2026
Marriott Chicago O'Hare
8535 West Higgins Road Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$304 per night from 3 Apr to 4 Apr
NZ$304
3 Apr - 4 Apr
includes taxes & fees
8.6/10 Excellent! (1,237 reviews)
Our room was super hot thermostat was working
Reviewed on 28 Mar 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
4.5/5(21 reviews)
A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.
Naval Base Great Lakes
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.
McCormick Place
4.5/5(21 reviews)
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.
What to do in Highwood
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.