Hometown Holidays from NZ$2,859
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The Latest Hometown Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was NZ$5,454, price is now NZ$3,814 per person
NZ$3,814
per person
30 Oct - 4 Nov
found 5 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
We picked the Trump Hotel-Chicago to celebrate our 35th Wedding Anniversary mainly for the location and the amenities. The hotel EXCEEDED our expectations in every way. (1) The staff is so warm, kind, compassionate and extremely professional in such a friendly down-to-earth way. (2) The property itself is immaculate. (3) The amenities: Terrace 16- the view will take your breath away! The food/cocktails were fabulous as was the service. (3) Pablo - Director of Rooms, Curtis -Concierge were off the charts fabulous. I wish I could remember all the staff names that went out of their way to make our weekend so special. I cannot wait to stay here again. As another reviewer said: put any political opinions aside and treat yourself to a stay here. YOU WILL LOVE IT. (There is no political aura here...only a fantastic team that wants you to enjoy your stay and they go out of their way to make sure you do).
Reviewed on 8 Sep. 2025
The Emily Hotel
Downtown Chicago
Price was NZ$4,112, price is now NZ$3,090 per person
NZ$3,090
per person
30 Oct - 4 Nov
found 5 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,195 reviews)
The rooms were not very well decorated. The furniture used in the room looks like furniture from a detention house. Not my favorite.
Reviewed on 8 Sep. 2025
Pendry Chicago
Downtown Chicago
Price was NZ$4,061, price is now NZ$3,181 per person
NZ$3,181
per person
30 Oct - 4 Nov
found 5 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,070 reviews)
The property is gorgeous! Lovely rooms and the staff were fantastic, could not fault them at all! My only issue would be the roads outside are very noisy, we needed ear plugs to sleep. Other than that, absolutely fantastic stay! Would return and would highly recommend
Reviewed on 8 Sep. 2025
Hometown Holiday
Our pick of the best Hometown Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$390 per night from 13 Sept to 14 Sept
NZ$390
13 Sept - 14 Sept
includes taxes & fees
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$363 per night from 22 Sept to 23 Sept
NZ$363
22 Sept - 23 Sept
includes taxes & fees
Freehand Chicago
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$229 per night from 23 Sept to 24 Sept
NZ$229
23 Sept - 24 Sept
includes taxes & fees
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 Hometown
Wrigley Field
A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.
Navy Pier
One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.
McCormick Place
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 Hometown
Wendella's 90-min Chicago River Architecture Tour
NZ$76
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
NZ$76
per adult
96% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
