
Gary Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 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
Gary Holiday
Our pick of the best Gary Hotel Deals

Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$250 per night from 22 Nov to 23 Nov
NZ$250
22 Nov - 23 Nov
includes taxes & fees
8/10 Very good! (10,095 reviews)
"We had a wonderful stay in Chicago! The hotel was great overall, and the staff really made the experience even better. John, the bartender, was fantastic, and Tina, who served us breakfast, was just the sweetest. Both deserve a special shoutout for making us feel so welcome. One thing I would love ..."
Reviewed on 15 Nov 2026

Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$344 per night from 22 Nov to 23 Nov
NZ$344
22 Nov - 23 Nov
includes taxes & fees
8.6/10 Excellent! (3,552 reviews)
"We paid for a lake view front room, but we got put in a different room once we got to the hotel. The room was over 75 degrees when we entered, and never cooled down. Other than that, the staff was great. But for the price, there’s a lot of better options."
Reviewed on 15 Nov 2026

Sentral Michigan Avenue
808 SOUTH MICHIGAN AVENUE Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$406 per night from 13 Dec to 14 Dec
NZ$406
13 Dec - 14 Dec
includes taxes & fees
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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



