Highwood Holidays from NZ$2,818
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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$3,760, price is now NZ$2,818 per person
NZ$2,818
per person
31 Oct - 5 Nov
found 15 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 15 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 15 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
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$412 per night from 25 Oct to 26 Oct
NZ$412
25 Oct - 26 Oct
includes taxes & fees
8.2/10 Very Good! (2,145 reviews)
"Super convenient because it’s right at the airport. But very old and tired. Needs an update!"
Reviewed on 22 Sept 2025
Marriott Chicago O'Hare
8535 West Higgins Road, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$346 per night from 24 Oct to 25 Oct
NZ$346
24 Oct - 25 Oct
includes taxes & fees
8.4/10 Very Good! (1,159 reviews)
"Great!!!"
Reviewed on 23 Sept 2025
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave, Rosemont, IL
Fully refundableReserve now, pay when you stay
The price is NZ$300 per night from 29 Oct to 30 Oct
NZ$300
29 Oct - 30 Oct
includes taxes & fees
8.6/10 Excellent! (2,013 reviews)
"staff was pleasant and professional"
Reviewed on 25 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.
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.
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.
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
Chicago Sightseeing River and Lake Cruise
NZ$77
per adult
100% of travellers recommend
Wendella's Lake and River Architecture Tour
NZ$77
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
