Winthrop Harbor Holidays from NZ$2,216
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$616 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Winthrop Harbor 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
Winthrop Harbor Holiday
Our pick of the best Winthrop Harbor Hotel Deals
Motel Sun Inn
301 Sheridan Road, Winthrop Harbor, IL
Fully refundableReserve now, pay when you stay
The price is NZ$116 per night from 16 Nov to 17 Nov
NZ$116
16 Nov - 17 Nov
includes taxes & fees
6.8/10 (272 reviews)
Clean rooms. Friendly owners.
Reviewed on 20 Oct 2025
LA VILLA MOTEL
1401 Sheridan Rd, Winthrop Harbor, IL
Fully refundable
The price is NZ$126 per night from 19 Nov to 20 Nov
NZ$126
19 Nov - 20 Nov
includes taxes & fees
6.6/10 (65 reviews)
Good service
Reviewed on 30 Sept 2025
La Quinta Inn & Suites by Wyndham Chicago Gurnee
5688 Northridge Rd, Gurnee, IL
Fully refundableReserve now, pay when you stay
The price is NZ$133 per night from 16 Nov to 17 Nov
NZ$133
16 Nov - 17 Nov
includes taxes & fees
7.8/10 Good! (1,399 reviews)
Check in was great. The staff was kind and courteous.
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.
More holiday ideas
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
