
Highland Hills Holidays from NZ$2,500
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Top Holiday Package Deals in Highland Hills
Price found within the past 48 hours. Click for updated prices.

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was NZ$3,080, price is now NZ$2,500 per person
NZ$2,500
per person
24 Dec - 29 Dec
found 24 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel
Reviewed on 20 Oct 2025

Pendry Chicago
Downtown Chicago
Price was NZ$3,528, price is now NZ$2,711 per person
NZ$2,711
per person
24 Dec - 29 Dec
found 24 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly.
Reviewed on 16 Oct 2025

The Emily Hotel
Downtown Chicago
Price was NZ$3,357, price is now NZ$2,676 per person
NZ$2,676
per person
24 Dec - 29 Dec
found 24 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,248 reviews)
We really like The Emily Hotel Chicago. We've stayed a few times this year because the location is very near many great restaurants and bars. The hotel itself has really good dining and lounge options. The staff treats us very well and the rooms and beds are clean and comfortable. A great hotel in a really fun part of town!
Reviewed on 22 Oct 2025

Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was NZ$3,342, price is now NZ$2,704 per person
NZ$2,704
per person
24 Dec - 29 Dec
found 24 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (303 reviews)
Food price was high but everything was fine
Reviewed on 4 Oct 2025

Arlo Chicago
Downtown Chicago
Price was NZ$3,098, price is now NZ$2,514 per person
NZ$2,514
per person
24 Dec - 29 Dec
found 24 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,852 reviews)
We had an amazing time staying at the Arlo. The staff was very friendly, the check-in/check-out process was very fast. The room was always clean. The location of the hotel is extremely convenient. Everything was awesome. I’m 100% coming back when I’m in Chicago again.
Reviewed on 22 Oct 2025
Our guide on 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.
Our pick of the best 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 NZ$156 per night from 26 Oct to 27 Oct
NZ$156
26 Oct - 27 Oct
includes taxes & fees
8.8/10 Excellent! (2,308 reviews)
Great place close to ORD airport.
Reviewed on 19 Oct 2025

Holiday Inn Chicago Dwtn - The Mart by IHG
350 West Wolf Point Plaza, Building 2, Chicago, IL
Fully refundable
The price is NZ$283 per night from 23 Nov to 24 Nov
NZ$283
23 Nov - 24 Nov
includes taxes & fees
8.8/10 Excellent! (1,943 reviews)
Great location if you have meetings at the Mart which you can reach through escalator and a bridge that takes you directly to the second floor. The hotel is well run Good breakfast and friendly staff. Rooms are clean but they should start “refreshing” some of the features like carpets which seem ...
Reviewed on 13 Oct 2025

Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street, Chicago, IL
Fully refundable
The price is NZ$216 per night from 23 Nov to 24 Nov
NZ$216
23 Nov - 24 Nov
includes taxes & fees
8.8/10 Excellent! (1,605 reviews)
Clean with great water pressure, plenty of hot water and excellent bedding. But most of all friendly and helpful staff.
Reviewed on 16 Oct 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.
Frequently asked questions
Discover the most popular places to visit in Highland Hills

Wrigley Field
A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.

Navy Pier
One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

McCormick Place
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.
Activities

Skydeck - Willis Tower Admission
NZ$77
per adult
100% of travellers recommend

Chicago Sightseeing River and Lake Cruise
NZ$79
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.




