Highland Holidays from NZ$2,398
Book a Hotel + Flight or Car together to unlock savings
Photo by Joe Farmer
- 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
The Latest Highland Holiday Deals
Price found within the past 48 hours. Click for updated prices.
The Emily Hotel
Downtown Chicago
Price was NZ$2,807, price is now NZ$2,398 per person
NZ$2,398
per person
22 Dec - 27 Dec
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,248 reviews)
Perfect stay and location. Room was clean and just what we needed. It’s nothing special
Reviewed on 11 Nov 2025
The Peninsula Chicago
Downtown Chicago
Price was NZ$4,972, price is now NZ$3,955 per person
NZ$3,955
per person
22 Dec - 27 Dec
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.8/10 Exceptional! (1,009 reviews)
Staff is always there for your every need. Excellent clean room. Quiet and luxurious
Reviewed on 7 Nov 2025
Hilton Chicago O'Hare Airport
O'Hare
Price was NZ$3,421, price is now NZ$2,831 per person
NZ$2,831
per person
22 Dec - 27 Dec
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
8.2/10 Very Good! (2,141 reviews)
It's an old airport hotel. What does one should expect, 5 stars?? Served the purpose. Didn't eat food only slept for one night due to the flight cancelation.
Reviewed on 10 Nov 2025
Highland Holiday
Our pick of the best Highland Hotel Deals
Hilton Chicago/Oak Lawn
9333 S Cicero Ave, Oak Lawn, IL
Fully refundableReserve now, pay when you stay
The price is NZ$259 per night from 25 Nov to 26 Nov
NZ$259
25 Nov - 26 Nov
includes taxes & fees
8.2/10 Very Good! (1,109 reviews)
Perfect
Reviewed on 9 Nov 2025
Motel 6 - Chicago, IL
10022 South Halsted Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$140 per night from 5 Dec to 6 Dec
NZ$140
5 Dec - 6 Dec
includes taxes & fees
6.6/10 (157 reviews)
Awesome staff, very understanding, maids were awesome and extremely helpful. Overall this staff seemed to work together as a team and get whatever task that needed to be done, they definetely deserve a pat on the back and I will recommend anyone to stay hqqj
Reviewed on 4 Nov 2025
Ameristar Casino Hotel East Chicago
777 Ameristar Blvd., East Chicago, IN
Fully refundableReserve now, pay when you stay
8.4/10 Very Good! (1,002 reviews)
The room was perfect! Clean, spacious and overall very good! The employees also so nice!
Reviewed on 2 Nov 2025
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.
More holiday ideas
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
