Cherry Holidays from NZ$2,045
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to NZ$616 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
The Latest Cherry Holiday Deals
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
Price was NZ$2,596, price is now NZ$2,045 per person
NZ$2,045
per person
4 Nov - 9 Nov
found 4 hours ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9.2/10 Wonderful! (2,120 reviews)
The hotel staff was great from the door men to front desk staff everyone was great.
Reviewed on 23 Sept 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was NZ$4,661, price is now NZ$3,143 per person
NZ$3,143
per person
4 Nov - 9 Nov
found 4 hours ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Worth every penny! Not much more than the "average" hotel when comparing all of the amenities. Will definitely stay here again!
Reviewed on 23 Sept 2025
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was NZ$2,946, price is now NZ$2,122 per person
NZ$2,122
per person
4 Nov - 9 Nov
found 4 hours ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The room was perfect and the front staff were exceptional. Our stay was amazing!
Reviewed on 21 Sept 2025
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was NZ$3,179, price is now NZ$2,500 per person
NZ$2,500
per person
4 Nov - 9 Nov
found 4 hours ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9.4/10 Exceptional! (3,344 reviews)
Wonderful stay with wonderful views!
Reviewed on 22 Sept 2025
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was NZ$2,963, price is now NZ$2,347 per person
NZ$2,347
per person
4 Nov - 9 Nov
found 4 hours ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9.4/10 Exceptional! (2,142 reviews)
Great view and a great staff!
Reviewed on 22 Sept 2025
Cherry Holiday
Our pick of the best Cherry Hotel Deals
Grand Bear Resort at Starved Rock
2643 IL-178, Utica, IL
The price is NZ$212 per night from 22 Oct to 23 Oct
NZ$212
22 Oct - 23 Oct
includes taxes & fees
7.2/10 Good! (929 reviews)
"I woild recommemd Grand Bear Lodge simply for this; its family friendly outside a major urban area where you can enjoy nature in safety."
Reviewed on 15 Sept 2025
Days Inn by Wyndham Oglesby/ Starved Rock
120 N Lewis Ave, Oglesby, IL
Fully refundableReserve now, pay when you stay
The price is NZ$160 per night from 28 Sept to 29 Sept
NZ$160
28 Sept - 29 Sept
includes taxes & fees
8/10 Very Good! (1,006 reviews)
"Was clean and confortable"
Reviewed on 14 Sept 2025
La Quinta Inn & Suites by Wyndham Peru Starved Rock St Park
4389 Venture Dr, Peru, IL
Fully refundableReserve now, pay when you stay
The price is NZ$188 per night from 12 Oct to 13 Oct
NZ$188
12 Oct - 13 Oct
includes taxes & fees
7.6/10 Good! (118 reviews)
"Great restaurant. Jalapenas. Really good food. Walkable. We were looking forward to using the hot tub, but it was pretty dirty with clumps of hair floating. Hadn’t been cleaned in a while. Check in and staff were very pleasant. We also had a barking dog for part of the evening."
Reviewed on 20 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.
More holiday ideas
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
