Monticello Holidays from NZ$787
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
The Latest Monticello Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago
Downtown Chicago
Price was NZ$998, price is now NZ$787 per person
NZ$787
per person
14 Aug - 16 Aug
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
8.8/10 Excellent! (1,008 reviews)
Would definitely stay here again! Clean, friendly staff, great location.
Reviewed on 23 May 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was NZ$1,164, price is now NZ$878 per person
NZ$878
per person
14 Aug - 16 Aug
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
8.2/10 Very Good! (2,711 reviews)
Great location, quiet room and nice staff. Hotel is a bit dated, but would still stay again. TV alaram went off at 6 AM did not know it was set to on.
Reviewed on 23 May 2026
L7 Chicago by LOTTE
Downtown Chicago
Price was NZ$1,106, price is now NZ$885 per person
NZ$885
per person
14 Aug - 16 Aug
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
9.6/10 Exceptional! (4,041 reviews)
Upon check-in, Alex was kind and helpful. He gave us some great tips about the hotel and some things to explore and where to eat. Alex was moved by our mother-daughter trip before my daughter travels to Spain to study. He even left us a sweet treat which was a perfect end to our evening. The room, the view, and the shower were absolutely perfect! We will be back to Chicago and because of Alex we will only be staying at L7 when we do. Thanks for your kind words, Alex.
Reviewed on 24 May 2026
Swissotel - Chicago
Downtown Chicago
Price was NZ$1,202, price is now NZ$964 per person
NZ$964
per person
14 Aug - 16 Aug
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
9/10 Wonderful! (3,332 reviews)
Great location and very convenient to river walk and vicinity.
Reviewed on 22 May 2026
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! (158 reviews)
"With the late night arrival, I was so grateful for flexibility and coffee plus creamer for the next morning!Very peaceful and perfect for our family’s visit."
Reviewed on 3 May 2026
Tru by Hilton Madison West, WI
8102 Watts Rd. Madison WI
Fully refundableReserve now, pay when you stay
The price is NZ$158 per night from 7 June to 8 June
NZ$158
7 June - 8 June
includes taxes & fees
9.4/10 Exceptional! (1,011 reviews)
"Good stay"
Reviewed on 23 May 2026
Super 8 by Wyndham Madison South
1602 W Beltline Hwy Madison WI
Fully refundableReserve now, pay when you stay
The price is NZ$118 per night from 1 June to 2 June
NZ$118
1 June - 2 June
includes taxes & fees
7/10 Good! (1,004 reviews)
"The room was clean and the breakfast set up was nice"
Reviewed on 23 May 2026
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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
