Highland Holidays from NZ$2,818
Book a Hotel + Flight or Car together to unlock savings
Photo by Joe Farmer
- Plan, book, travel with confidence
Better together
Save up to NZ$616 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, 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.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was NZ$3,760, price is now NZ$2,818 per person
NZ$2,818
per person
31 Oct - 5 Nov
found 11 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The WIt was everything. The Roof at the Wit, was amazing, be sure to make reservations. I love this hotel and Chicago it was safe and close to everything!!
Reviewed on 26 Sept 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was NZ$5,759, price is now NZ$3,908 per person
NZ$3,908
per person
31 Oct - 5 Nov
found 11 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
It’s was very clean and safe
Reviewed on 27 Sept 2025
The Emily Hotel
Downtown Chicago
Price was NZ$4,292, price is now NZ$3,151 per person
NZ$3,151
per person
31 Oct - 5 Nov
found 11 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
The Emily Hotel was in a convenient area of Chicago close to the family wedding we were attending in mid-September.
Rooms were clean modern and had loads of desk space but no dressers or nightstands.
Staff was helpful in telling us about the nearby parking garage beneath the Google building across the street. We parked our car there for $57/ day vs Valet for $85 (with unlimited in and) at The Emily.
We would stay there again.
Reviewed on 26 Sept 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$245 per night from 5 Oct to 6 Oct
NZ$245
5 Oct - 6 Oct
includes taxes & fees
8.2/10 Very Good! (1,047 reviews)
"The circular hotel is clean, safe, and in an area with lots of food and shopping. It is only a few miles South of Midway Airport and is a straight shot to get there. When I come to Chicago again, I will definitely stay here! Pro Tip: I paid $20 per night for parking, but there is plenty of free street ..."
Reviewed on 24 Sept 2025
Motel 6 - Chicago, IL
10022 South Halsted Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$137 per night from 13 Oct to 14 Oct
NZ$137
13 Oct - 14 Oct
includes taxes & fees
6.6/10 (113 reviews)
"My next door neighbors, were a bit loud. But they did quite down."
Reviewed on 24 Sept 2025
Baymont by Wyndham Chicago/Alsip
12801 South Cicero, Alsip, IL
Fully refundableReserve now, pay when you stay
The price is NZ$195 per night from 28 Sept to 29 Sept
NZ$195
28 Sept - 29 Sept
includes taxes & fees
8/10 Very Good! (1,023 reviews)
"The hotel was nice and clean! Bed slept wonderful. There are minor things that can be touched up like the bathroom shower floor needed caulk and the actual mattress under the pad lol.... yes im a housekeeper but other than that it was fairly clean down to the bed and carpet and"
Reviewed on 24 Sept 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.
