Monticello Holidays from NZ$3,146
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The Latest Monticello Holiday Deals
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 1 day 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 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
18/10 Exceptional! (380 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 1 day 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 1 day 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
Monticello Holiday
Our pick of the best Monticello Hotel Deals
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
Monticello WI
10/10 Exceptional! (156 reviews)
Nice and clean. Close to town, but out in the country with a beautiful backyard with a fire pit.
Reviewed on 3 Nov 2025
Baymont Inn & Suites by Wyndham Madison
2810 Coho Street Madison WI
Fully refundableReserve now, pay when you stay
The price is NZ$104 per night from 18 Dec to 19 Dec
NZ$104
18 Dec - 19 Dec
includes taxes & fees
7.2/10 Good! (1,498 reviews)
Very bright hotel, friendly staff. Room was very spacious, bed was very soft in my younger days wouldve been great but not so much in my now older days. Don't get me wrong was still very comfortable. Pool and hot tub could've been cleaned better. Only major complaint i have is none of the outer doors ...
Reviewed on 13 Nov 2025
Best Western West Towne Suites
650 Grand Canyon Dr Madison WI
Fully refundableReserve now, pay when you stay
The price is NZ$156 per night from 30 Nov to 1 Dec
NZ$156
30 Nov - 1 Dec
includes taxes & fees
8.6/10 Excellent! (1,184 reviews)
Nice and clean, safe grounds.
Reviewed on 15 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
