Southern Wisconsin Luxury Holidays
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Top flight + Luxury hotel deals in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was NZ$3,080, price is now NZ$2,500 per person
NZ$2,500
per person
24 Dec - 29 Dec
found 1 hour ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel
Reviewed on 20 Oct 2025
Pendry Chicago
Downtown Chicago
Price was NZ$3,528, price is now NZ$2,711 per person
NZ$2,711
per person
24 Dec - 29 Dec
found 1 hour ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly.
Reviewed on 16 Oct 2025
The Emily Hotel
Downtown Chicago
Price was NZ$3,357, price is now NZ$2,676 per person
NZ$2,676
per person
24 Dec - 29 Dec
found 1 hour ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,248 reviews)
We really like The Emily Hotel Chicago. We've stayed a few times this year because the location is very near many great restaurants and bars. The hotel itself has really good dining and lounge options. The staff treats us very well and the rooms and beds are clean and comfortable. A great hotel in a really fun part of town!
Reviewed on 22 Oct 2025
Arlo Chicago
Downtown Chicago
Price was NZ$3,098, price is now NZ$2,514 per person
NZ$2,514
per person
24 Dec - 29 Dec
found 1 hour ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,852 reviews)
We had an amazing time staying at the Arlo. The staff was very friendly, the check-in/check-out process was very fast. The room was always clean. The location of the hotel is extremely convenient. Everything was awesome. I’m 100% coming back when I’m in Chicago again.
Reviewed on 22 Oct 2025
The Ritz-Carlton, Chicago
Downtown Chicago
Price was NZ$4,398, price is now NZ$3,596 per person
NZ$3,596
per person
24 Dec - 29 Dec
found 1 hour ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
Be prepared to be treated like you are the most important guest at the hotel. The staff here is incredibly professional, helpful and service oriented. Every single one.
Reviewed on 15 Sept 2025
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View all trips5* Luxury holidays in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
The Ritz-Carlton, Chicago
Downtown Chicago
Price was NZ$4,398, price is now NZ$3,596 per person
NZ$3,596
per person
24 Dec - 29 Dec
found 1 hour ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
Be prepared to be treated like you are the most important guest at the hotel. The staff here is incredibly professional, helpful and service oriented. Every single one.
Reviewed on 15 Sept 2025
Don't see what you're looking for?
See all available trips from Columbus to Southern Wisconsin
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
