Chicago Holidays
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Our guide on where to stay in Chicago
Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago
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.
Chicago Holiday
Our pick of the best Chicago Hotel Deals
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$243 per night from 23 Nov to 24 Nov
NZ$243
23 Nov - 24 Nov
includes taxes & fees
8.4/10 Very Good! (5,174 reviews)
Completely fell in love with the hotel!
Reviewed on 30 Oct 2025
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$335 per night from 7 Nov to 8 Nov
NZ$335
7 Nov - 8 Nov
includes taxes & fees
7.8/10 Good! (9,665 reviews)
Yes
Reviewed on 3 Nov 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$210 per night from 17 Nov to 18 Nov
NZ$210
17 Nov - 18 Nov
includes taxes & fees
8.8/10 Excellent! (3,220 reviews)
Great staff at the front desk!
Reviewed on 2 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.
Discover the most popular places to visit in Chicago
Wrigley Field
4.5/5(21 reviews)
A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.
Navy Pier
4.5/5(64 reviews)
One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.
McCormick Place
4.5/5(21 reviews)
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 Chicago
Skydeck - Willis Tower Admission
NZ$76
per adult
98% of travellers recommend
Chicago Sightseeing River and Lake Cruise
NZ$78
per adult
100% of travellers recommend
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