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
7.8/10 Good! (9,307 reviews)
"Parking situation is ridicules, hallways carpet very filthy. I understand it’s an older hotel but needs to be kept up. Bathroom door didn’t even close."
Reviewed on 25 Sept 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$324 per night from 20 Oct to 21 Oct
NZ$324
20 Oct - 21 Oct
includes taxes & fees
8.8/10 Excellent! (2,962 reviews)
"Hotel was very nice but the parking was ridiculous, $80 for valet parking per day. Luckily a staff member directed us to a parking garage right across the street for $45. There is a lot to see within walking distance. Some of the staff weren't very friendly."
Reviewed on 25 Sept 2025
Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$363 per night from 2 Oct to 3 Oct
NZ$363
2 Oct - 3 Oct
includes taxes & fees
8.4/10 Very Good! (3,934 reviews)
"It was walking distance to Michigan Ave"
Reviewed on 21 Sept 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 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.
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 Hillside
Wendella's 90-min Chicago River Architecture Tour
NZ$77
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
NZ$77
per adult
96% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
