Chesterton Holidays from NZ$2,260
Book a Hotel + Flight or Car together to unlock savings
Photo by Indiana Office of Tourism Development
- 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 Chesterton Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was NZ$2,615, price is now NZ$2,260 per person
NZ$2,260
per person
22 Dec - 27 Dec
found 10 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (2,188 reviews)
It was so relaxing and peaceful
Reviewed on 9 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 10 hours 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$3,882, price is now NZ$3,296 per person
NZ$3,296
per person
21 Dec - 26 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
The Emily Hotel
Downtown Chicago
Price was NZ$2,807, price is now NZ$2,398 per person
NZ$2,398
per person
22 Dec - 27 Dec
found 10 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,248 reviews)
Perfect stay and location. Room was clean and just what we needed. It’s nothing special
Reviewed on 11 Nov 2025
Chesterton Holiday
Our pick of the best Chesterton Hotel Deals
Spring House Inn
303 N Mineral Springs Rd, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is NZ$205 per night from 12 Nov to 13 Nov
NZ$205
12 Nov - 13 Nov
includes taxes & fees
8.8/10 Excellent! (1,046 reviews)
This was the cutest place! The surrounding area is gorgeous! The swings and fire were absolutely lovely!
Reviewed on 3 Nov 2025
Best Western Indian Oak
558 Indian Boundary Road, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is NZ$186 per night from 17 Nov to 18 Nov
NZ$186
17 Nov - 18 Nov
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
Fantastic and friendly staff. Clean, nice hotel.
Reviewed on 29 Oct 2025
Comfort Inn & Suites Porter near Indiana Dunes
1800 West US Highway 20, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is NZ$186 per night from 11 Dec to 12 Dec
NZ$186
11 Dec - 12 Dec
includes taxes & fees
8/10 Very Good! (1,001 reviews)
My room was clean and comfortable. I would definitely stay here again
Reviewed on 28 Oct 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.
