
The Loop Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
- Le Méridien Essex Chicago
Aug 14 - Aug 16Le Méridien Essex Chicago + Flight
Downtown Chicago2 nights8.8/10 - Excellent (1,000 reviews)"Great day super nice staff and very helpful comfortable clean, and a great location at a reasonable price very pleased"Reviewed May 20, 2026Return • New York (LGA) - Chicago (ORD)LGA - ORD • Direct ORD - JFK • DirectNZ$999NZ$787found 7 hours agoper traveller - Hotel Felix River North/Magnificent Mile
Aug 14 - Aug 16Hotel Felix River North/Magnificent Mile + Flight
Downtown Chicago2 nights8.2/10 - Very good (2,715 reviews)"A decent buisness class hotel. No frills. Rooms are smaller, the queen beds are not true queens, and much smaller."Reviewed May 22, 2026Return • New York (LGA) - Chicago (ORD)LGA - ORD • Direct ORD - JFK • DirectNZ$1,164NZ$878found 7 hours agoper traveller - Fairmont Chicago at Millennium Park
Aug 14 - Aug 16Fairmont Chicago at Millennium Park + Flight
Downtown Chicago2 nights8.8/10 - Excellent (2,164 reviews)"Amazing staff. Clean rooms!"Reviewed May 21, 2026Return • New York (LGA) - Chicago (ORD)LGA - ORD • Direct ORD - JFK • DirectNZ$1,127NZ$859found 7 hours agoper traveller - L7 Chicago by LOTTE
Aug 14 - Aug 16L7 Chicago by LOTTE + Flight
Downtown Chicago2 nights9.6/10 - Exceptional (4,076 reviews)"The property has a very convenient location. The room is spacious. They offer free but good coffee and popcorn at the lobby every day. And the cold water from the tab is filtered. Definitely will come back."Reviewed May 22, 2026Return • New York (LGA) - Chicago (ORD)LGA - ORD • Direct ORD - JFK • DirectNZ$1,106NZ$885found 7 hours agoper traveller - Swissotel - Chicago
Aug 14 - Aug 16Swissotel - Chicago + Flight
Downtown Chicago2 nights9.0/10 - Wonderful (3,336 reviews)"Great location and very convenient to river walk and vicinity."Reviewed May 22, 2026Return • New York (LGA) - Chicago (ORD)LGA - ORD • Direct ORD - JFK • DirectNZ$1,201NZ$964found 7 hours agoper traveller
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
The price is NZ$271 per night from 25 May to 26 May
NZ$271
25 May - 26 May
includes taxes & fees
8/10 Very Good! (10,131 reviews)
"Did not have hot water when we returned to room after concert. Next morning called and maintenance came to fix. Good location to walk to South Shore train station and Grant Park"
Reviewed on 23 May 2026

River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$240 per night from 26 May to 27 May
NZ$240
26 May - 27 May
includes taxes & fees
8.8/10 Excellent! (5,190 reviews)
"The staff was very helpful and friendly."
Reviewed on 22 May 2026

Fairmont Chicago at Millennium Park
200 North Columbus Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$401 per night from 25 May to 26 May
NZ$401
25 May - 26 May
includes taxes & fees
8.8/10 Excellent! (2,164 reviews)
"Amazing staff. Clean rooms!"
Reviewed on 21 May 2026
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.

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

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.
Activities

Skydeck - Willis Tower Admission
NZ$74
per adult
96% of travellers recommend

Chicago Sightseeing River and Lake Cruise
NZ$77
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



















