
Half Day Holidays from NZ$3,146
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Top Holiday Package Deals in Half Day
Price found within the past 48 hours. Click for updated prices.

Pendry Chicago
Downtown Chicago
Price was NZ$4,303, price is now NZ$3,146 per person
NZ$3,146
per person
26 Dec - 2 Jan
found 5 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
18.8/10 Exceptional! (1,130 reviews)
The room had no soundproofing. Every night a car was revving loudly across Michigan Ave around midnight, making it impossible to sleep without noise-cancelling AirPods.
Reviewed on 18 Nov 2025

Level Chicago – Old Town
Downtown Chicago
Price was NZ$6,133, price is now NZ$4,038 per person
NZ$4,038
per person
26 Dec - 2 Jan
found 4 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.
Reviewed on 9 Nov 2025

The Emily Hotel
Downtown Chicago
Price was NZ$5,140, price is now NZ$3,607 per person
NZ$3,607
per person
26 Dec - 2 Jan
found 5 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
18.4/10 Exceptional! (1,264 reviews)
Perfect stay and location. Room was clean and just what we needed. It’s nothing special
Reviewed on 11 Nov 2025


Trump International Hotel & Tower Chicago
Downtown Chicago
Price was NZ$6,630, price is now NZ$4,802 per person
NZ$4,802
per person
26 Dec - 2 Jan
found 5 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
18.8/10 Exceptional! (1,773 reviews)
Political stigma aside, I must say, this property is stunning across the board. From the moment you enter the building you're met with this amazingly inviting fragrance.
The Room was spotless. All the staff was sincere, kind, hospitable, and surprisingly diverse. Also, The front desk was exceptionally accommodating while I (minimally) "stress tested" the room service. 10/10 would and Will return.
Mr. & Mrs.S
Reviewed on 17 Nov 2025
Our guide on where to stay in Half Day
Find the best Half Day areas and neighborhoods for the activities you enjoy most. Learn more about Half Day

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 Half Day Hotel Deals

Staybridge Suites, Lincolnshire by IHG
100 Barclay Blvd Lincolnshire IL
Fully refundableReserve now, pay when you stay
The price is NZ$195 per night from 19 Dec to 20 Dec
NZ$195
19 Dec - 20 Dec
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
Place was overall good , they upgraded me from a 1 to a 2 bedroom. Because i needed the shower that was handicap that i booked on expedia. They dont have 1 bedroom with handicap accessible shower as described. They can do better on the breakfast. Thats 1 complaint. 2nd complaint i extended for 1 ...
Reviewed on 10 Nov 2025

Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$405 per night from 19 Dec to 20 Dec
NZ$405
19 Dec - 20 Dec
includes taxes & fees
8.2/10 Very Good! (2,152 reviews)
Clean and quiet and comfortable
Reviewed on 14 Nov 2025

Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is NZ$279 per night from 15 Dec to 16 Dec
NZ$279
15 Dec - 16 Dec
includes taxes & fees
8.6/10 Excellent! (2,119 reviews)
All of the above
Reviewed on 12 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.
Frequently asked questions
Discover the most popular places to visit in Half Day

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

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.

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

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.




