Hillside Holidays
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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$270 per night from 26 May to 27 May
NZ$270
26 May - 27 May
includes taxes & fees
8/10 Very Good! (10,166 reviews)
"I had an amazing view of Lake Michigan and the area but unfortunately Michigan Ave is very noisy at all times of the day and night. In addition, there were no black out shades and due to the rooms facing East, the sunrise was bright and early. I had to buy a sleeping mask just to sleep to 7am. The ..."
Reviewed on 19 May 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$350 per night from 25 May to 26 May
NZ$350
25 May - 26 May
includes taxes & fees
9.4/10 Exceptional! (4,188 reviews)
"New amenities, awesome breakfast, great location. Pleasently surprised, especially by the quality of the breakfast."
Reviewed on 19 May 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$246 per night from 25 May to 26 May
NZ$246
25 May - 26 May
includes taxes & fees
7.8/10 Good! (1,435 reviews)
"Roof top bar was very limited. My room had not a strip of toilet paper. Conditioner was out! Had two shampoos and no body wash."
Reviewed on 19 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.
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.
Naval Base Great Lakes
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
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
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
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
