
The Loop Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to NZ$616 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
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
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 The Loop Hotel Deals

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
7.8/10 Good! (9,384 reviews)
"This is a beautiful historic Chicago downtown hotel across the street from Grant Park. However, some of the rooms and hallways are in need of updating."
Reviewed on 1 Oct 2025

The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$477 per night from 5 Oct to 6 Oct
NZ$477
5 Oct - 6 Oct
includes taxes & fees
8.8/10 Excellent! (2,098 reviews)
"Staff was excellent. Decor was very elegant and classy. Enjoyed my two nights here."
Reviewed on 1 Oct 2025

citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$393 per night from 30 Oct to 31 Oct
NZ$393
30 Oct - 31 Oct
includes taxes & fees
9.2/10 Wonderful! (3,897 reviews)
"This hotel is right off of Michigan Ave with many restaurants, stores, and museums. Excellent location."
Reviewed on 30 Sept 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
4.5/5(73 reviews)
See mind-bending sculptures, a musically-inspired lawn and giant water fountains that double-up as video screens.

Art Institute of Chicago
4.5/5(32 reviews)
The Art Institute Of Chicago's far-ranging and brilliant collections make it one of the world’s finest art museums.

Willis Tower
4.5/5(39 reviews)
The Willis Tower is at its best when you're dangled over one of its glass-bottomed balconies 396 metres above Chicago.
Activities

Chicago Sightseeing River and Lake Cruise
NZ$77
per adult
100% of travellers recommend

Wendella's Lake and River Architecture Tour
NZ$77
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.