Highwood Holidays from NZ$2,216
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The Latest Highwood Holiday Deals
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was NZ$2,620, price is now NZ$2,216 per person
NZ$2,216
per person
22 Dec - 27 Dec
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
My room was very clean. The stay was very friendly and helpful. Check-in was a breeze. Since my room was ready they even let me check in early!
There are 2 restaurants in this hotel. We had drinks at the one near the lobby and we ate at the ROOF. The food was delish! The environment was fun. We were worried that it was going to be more for the 20 something crowd, but there were adults of every age there.
This hotel is also just steps from The Chicago Theatre which makes it super convenient when seeing an event there.
Reviewed on 10 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$3,422, price is now NZ$2,832 per person
NZ$2,832
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
Highwood Holiday
Our pick of the best Highwood Hotel Deals
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
1200 N Mittel Blvd, Wood Dale, IL
Fully refundableReserve now, pay when you stay
The price is NZ$175 per night from 23 Nov to 24 Nov
NZ$175
23 Nov - 24 Nov
includes taxes & fees
8/10 Very Good! (1,010 reviews)
Breakfast was excellent, very clean inside hotel and lobby
Reviewed on 8 Nov 2025
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave, Rosemont, IL
Fully refundableReserve now, pay when you stay
The price is NZ$202 per night from 24 Nov to 25 Nov
NZ$202
24 Nov - 25 Nov
includes taxes & fees
8.6/10 Excellent! (2,104 reviews)
Staff were excellent and very helpful
Reviewed on 7 Nov 2025
Holiday Inn Chicago O'Hare – Rosemont by IHG
6600 Mannheim Road, building 2, Rosemont, IL
Fully refundable
The price is NZ$229 per night from 27 Nov to 28 Nov
NZ$229
27 Nov - 28 Nov
includes taxes & fees
8.8/10 Excellent! (2,558 reviews)
Clean & nice room but need to get an easier alarm clock & TV remote. The front desk couldn’t figure how to use the alarm either. TV is difficult to get to channels.
Reviewed on 8 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.
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.
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.
Navy Pier
4.5/5(64 reviews)
One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.
What to do in Highwood
Skydeck - Willis Tower Admission
NZ$76
per adult
98% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
NZ$43
per adult
84% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
