Chicago Holiday Packages

Save when you book Chicago package deals

Choose two or more items and save on your trip:

Top Chicago holiday packages

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was NZ$2,618, price is now NZ$2,215 per person
NZ$2,215
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)
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was NZ$3,416, price is now NZ$2,828 per person
NZ$2,828
per person
22 Dec - 27 Dec
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
8.2/10 Very Good! (2,141 reviews)
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was NZ$2,688, price is now NZ$2,262 per person
NZ$2,262
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 Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was NZ$2,804, price is now NZ$2,396 per person
NZ$2,396
per person
22 Dec - 27 Dec
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,248 reviews)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was NZ$2,615, price is now NZ$2,260 per person
NZ$2,260
per person
22 Dec - 27 Dec
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (2,188 reviews)

Top Chicago hotels

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$245 per night from 25 Nov to 26 Nov
NZ$245
25 Nov - 26 Nov
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
Room was fine. Check in was not good. Front desk not helpful

Reviewed on 9 Nov 2025

Opens in a new windowHilton Chicago/Magnificent Mile Suites
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
The price is NZ$208 per night from 25 Nov to 26 Nov
NZ$208
25 Nov - 26 Nov
includes taxes & fees
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
Amazing Hotel, Quality,, Food and Service. Best place location wise as well.

Reviewed on 6 Nov 2025

Opens in a new windowEmbassy Suites by Hilton Chicago Downtown River North
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$308 per night from 15 Nov to 16 Nov
NZ$308
15 Nov - 16 Nov
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
a

Reviewed on 8 Nov 2025

Opens in a new windowCongress Plaza Hotel
Don't see what you're looking for?
See all available properties in Chicago
View all properties
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.