Chicago Holidays from NZ$3,128
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The Latest Chicago Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Dorothy's
Lakeview
Save 100% on your flight
per person
12 Jul - 18 Jul
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
8.4/10 Very Good! (24 reviews)
Parking is difficult. Closest designated spot was 2 blocks away. Booking was easy enough but communication between site and accommodation was inefficient. Email was not passed on for final access instructions to unmanned accommodation site. The finalisation process did not allow for visitors with International phone numbers to be contacted directly either. Login does not accept driver's licence picture.
Reviewed on 28 Apr. 2025
Level Chicago – Old Town
Downtown Chicago
per person
12 Jul - 18 Jul
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (295 reviews)
The staff wasn’t very welcoming. After booking, they send you a form asking for almost everything except your social security number. I understand it’s for the safety of the residents, but I didn’t feel comfortable providing that much information. It felt like I had no choice but to go through with it since I wouldn’t get my money back otherwise. The walls are also extremely thin; you can hear everything. One of the neighbors blasted music from 6 PM until 1 AM on a Tuesday. They only turned it down after I reported it. Overall, I wouldn’t stay here again.
Reviewed on 30 Apr. 2025
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
Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.
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$344 per night from 8 May to 9 May
NZ$344
includes taxes & fees
8 May - 9 May
8.2/10 Very Good! (3,957 reviews)
"Free drinks, great breakfast. Very clean, friendly staff, great location"
Reviewed on 30 Apr. 2025
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$282 per night from 8 May to 9 May
NZ$282
includes taxes & fees
8 May - 9 May
"Loved our stay! Cool historic hotel in an excellent location. Breakfast buffet was $29.95 and had wonderful variety of choices."
Reviewed on 28 Apr. 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$318 per night from 8 May to 9 May
NZ$318
includes taxes & fees
8 May - 9 May
"Pool and fitness center was not in service."
Reviewed on 28 Apr. 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.
Six Flags Great America
Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.
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
Chicago: Willis Tower Skydeck and The Ledge Ticket
NZ$75
per adult
86% of travellers recommend
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