
The Loop Holidays from NZ$3,146
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Top Holiday Package Deals in The Loop
Price found within the past 48 hours. Click for updated prices.

Pendry Chicago
Downtown Chicago
Price was NZ$4,303, price is now NZ$3,146 per person
NZ$3,146
per person
26 Dec - 2 Jan
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
18.8/10 Exceptional! (1,130 reviews)
The room had no soundproofing. Every night a car was revving loudly across Michigan Ave around midnight, making it impossible to sleep without noise-cancelling AirPods.
Reviewed on 18 Nov 2025

Level Chicago – Old Town
Downtown Chicago
Price was NZ$6,133, price is now NZ$4,038 per person
NZ$4,038
per person
26 Dec - 2 Jan
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
18/10 Exceptional! (380 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.
Reviewed on 9 Nov 2025

The Emily Hotel
Downtown Chicago
Price was NZ$5,140, price is now NZ$3,607 per person
NZ$3,607
per person
26 Dec - 2 Jan
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
18.4/10 Exceptional! (1,264 reviews)
Perfect stay and location. Room was clean and just what we needed. It’s nothing special
Reviewed on 11 Nov 2025


Trump International Hotel & Tower Chicago
Downtown Chicago
Price was NZ$6,630, price is now NZ$4,802 per person
NZ$4,802
per person
26 Dec - 2 Jan
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
18.8/10 Exceptional! (1,773 reviews)
Political stigma aside, I must say, this property is stunning across the board. From the moment you enter the building you're met with this amazingly inviting fragrance.
The Room was spotless. All the staff was sincere, kind, hospitable, and surprisingly diverse. Also, The front desk was exceptionally accommodating while I (minimally) "stress tested" the room service. 10/10 would and Will return.
Mr. & Mrs.S
Reviewed on 17 Nov 2025
Our guide on where to stay in The Loop
Find the best The Loop areas and neighborhoods for the activities you enjoy most. Learn more about The Loop

Downtown Chicago
4 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 The Loop Hotel Deals

Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$264 per night from 25 Nov to 26 Nov
NZ$264
25 Nov - 26 Nov
includes taxes & fees
8.4/10 Very Good! (2,057 reviews)
Excellent!
Reviewed on 13 Nov 2025

citizenM Chicago Downtown
80 East Wacker Place Chicago IL
The price is NZ$243 per night from 25 Nov to 26 Nov
NZ$243
25 Nov - 26 Nov
includes taxes & fees
9.2/10 Wonderful! (4,039 reviews)
Clean hotel, good location close to everything, friendly and helpful staff.
Reviewed on 17 Nov 2025

Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$202 per night from 24 Nov to 25 Nov
NZ$202
24 Nov - 25 Nov
includes taxes & fees
8/10 Very Good! (9,556 reviews)
Everything about the Congress was lovely. Enjoyed our stay. Perfect location for city adventure.
Reviewed on 14 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.
Frequently asked questions
Discover the most popular places to visit in The Loop

Millennium Park
See mind-bending sculptures, a musically-inspired lawn and giant water fountains that double-up as video screens.

Art Institute of Chicago
The Art Institute Of Chicago's far-ranging and brilliant collections make it one of the world’s finest art museums.

Willis Tower
The Willis Tower is at its best when you're dangled over one of its glass-bottomed balconies 396 metres above Chicago.
Activities

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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.




