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Hillside Holiday
Our pick of the best Hillside Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$217 per night from 26 Dec to 27 Dec
NZ$217
includes taxes & fees
26 Dec - 27 Dec
7.8/10 Good! (8,268 reviews)
"The hotel is very historic and beautifully decorated. We had a junior suite that was extremely roomy and very clean. The furniture was nice, but didn’t seem to match the historic charm of the hotel being that the decor in the room was ultra modern. The bathroom was huge, but the tub wasn’t updated ..."
Reviewed on 24 Dec. 2024
River Hotel
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$216 per night from 5 Jan to 6 Jan
NZ$216
includes taxes & fees
5 Jan - 6 Jan 2025
8.6/10 Excellent! (3,631 reviews)
Great!
"Staff was so helpful and kind. Loved our room too! Great stay-thank you!!"
Reviewed on 22 Dec. 2024
Hyatt Regency Chicago
151 East Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$359 per night from 6 Jan to 7 Jan
NZ$359
includes taxes & fees
6 Jan - 7 Jan 2025
9/10 Wonderful! (3,120 reviews)
"really enjoyed the city view from room."
Reviewed on 20 Dec. 2024
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 Hillside
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.
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.
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.
What to do in Hillside
Flyover in Chicago
NZ$68
per adult
96% of travellers recommend
Architecture River Tour
NZ$87
per adult
94% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
NZ$79
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.