
Little Italy Holidays from NZ$2,500
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Top Holiday Package Deals in Little Italy
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 8 hours 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 8 hours 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 8 hours 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

Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was NZ$3,342, price is now NZ$2,704 per person
NZ$2,704
per person
24 Dec - 29 Dec
found 8 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (303 reviews)
Food price was high but everything was fine
Reviewed on 4 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 8 hours 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
Our guide on where to stay in Little Italy
Find the best Little Italy areas and neighborhoods for the activities you enjoy most. Learn more about Little Italy

Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Our pick of the best Little Italy Hotel Deals

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$347 per night from 2 Nov to 3 Nov
NZ$347
2 Nov - 3 Nov
includes taxes & fees
7.8/10 Good! (9,498 reviews)
The website for the gazebo restaurant within the hotel said there was an extensive menu. When you get down to the place it’s a small buffett set up which was similar to any other continental breakfast with some cereal, muffins, fruit, some biscuits, bacon and sausage etc. There was also a man at ...
Reviewed on 20 Oct 2025

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$233 per night from 16 Nov to 17 Nov
NZ$233
16 Nov - 17 Nov
includes taxes & fees
8.8/10 Excellent! (3,133 reviews)
Every think was wonderful except the heater wasn’t working and the toilet was loose.
Reviewed on 19 Oct 2025

Freehand Chicago
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$168 per night from 12 Nov to 13 Nov
NZ$168
12 Nov - 13 Nov
includes taxes & fees
7.8/10 Good! (2,494 reviews)
Bathroom recently redone and was fabulous, but room was old and tattered. Bed was nice and comfy. Nice crisp sheets.
Reviewed on 18 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.
Frequently asked questions
Activities

Skydeck - Willis Tower Admission
NZ$77
per adult
100% of travellers recommend

Chicago Sightseeing River and Lake Cruise
NZ$79
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.




