Darien Holidays from NZ$2,216
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The Latest Darien Holiday Deals
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was NZ$2,620, price is now NZ$2,216 per person
NZ$2,216
per person
22 Dec - 27 Dec
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
My room was very clean. The stay was very friendly and helpful. Check-in was a breeze. Since my room was ready they even let me check in early!
There are 2 restaurants in this hotel. We had drinks at the one near the lobby and we ate at the ROOF. The food was delish! The environment was fun. We were worried that it was going to be more for the 20 something crowd, but there were adults of every age there.
This hotel is also just steps from The Chicago Theatre which makes it super convenient when seeing an event there.
Reviewed on 10 Nov 2025
Arlo Chicago
Downtown Chicago
Price was NZ$2,690, price is now NZ$2,263 per person
NZ$2,263
per person
22 Dec - 27 Dec
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,852 reviews)
The room was really clean and the staff was very friendly and accommodating
Reviewed on 10 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 9 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
8.2/10 Very Good! (2,141 reviews)
Staff was great and the room was clean!
We had to find a place for the night and didnt want to go far. It is convenient for that. Room rates are not too bad but the restaurant is a little pricey but still good food and service.
Reviewed on 9 Nov 2025
The Royal Sonesta Chicago Downtown
Downtown Chicago
Price was NZ$2,774, price is now NZ$2,360 per person
NZ$2,360
per person
22 Dec - 27 Dec
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (3,013 reviews)
Didn't know about breakfast bar.
Reviewed on 10 Nov 2025
The Ritz-Carlton, Chicago
Downtown Chicago
Price was NZ$4,357, price is now NZ$3,743 per person
NZ$3,743
per person
21 Dec - 26 Dec
found 9 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
Front desk staff definitely skipped the hospitality portion of training. From the greeting to the checkout no smiles no warmth not very inviting. The hotel and room itself was beautiful, great location but most likely will go to another hotel next time.
Reviewed on 24 Oct 2025
Darien Holiday
Our pick of the best Darien Hotel Deals
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$225 per night from 8 Dec to 9 Dec
NZ$225
8 Dec - 9 Dec
includes taxes & fees
8.4/10 Very Good! (5,199 reviews)
It was fine
Reviewed on 5 Nov 2025
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
8/10 Very Good! (9,538 reviews)
a
Reviewed on 8 Nov 2025
Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$195 per night from 7 Dec to 8 Dec
NZ$195
7 Dec - 8 Dec
includes taxes & fees
8.4/10 Very Good! (4,136 reviews)
Very convenient location. Room was clean. Decent restaurant on site, Weber Grill. I loved the location. Right next to Nordstrom and Michigan Ave. with lots of shopping options.
Reviewed on 7 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.
Discover the most popular places to visit in Darien
Wrigley Field
4.5/5(21 reviews)
A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.
Navy Pier
4.5/5(64 reviews)
One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.
McCormick Place
4.5/5(21 reviews)
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.
What to do in Darien
Skydeck - Willis Tower Admission
NZ$76
per adult
98% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
NZ$43
per adult
84% of travellers recommend
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