Hillside Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$616 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Hillside Holiday
Our pick of the best Hillside Hotel Deals
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$283 per night from 12 Apr to 13 Apr
NZ$283
12 Apr - 13 Apr
includes taxes & fees
9/10 Wonderful! (4,045 reviews)
Location was great. Valet parking was very accommodating-- extremely helpful
Reviewed on 4 Apr 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$224 per night from 5 Apr to 6 Apr
NZ$224
5 Apr - 6 Apr
includes taxes & fees
8/10 Very Good! (10,017 reviews)
Stayed here several times. This is the only place I stay in Chicago and always a five star experience!
Reviewed on 3 Apr 2026
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$313 per night from 12 Apr to 13 Apr
NZ$313
12 Apr - 13 Apr
includes taxes & fees
8.6/10 Excellent! (5,815 reviews)
Great experience
Reviewed on 4 Apr 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
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.
McCormick Place
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
Chicago Crime and Mob Bus Tour
NZ$84
per adult
92% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
NZ$69
per adult
94% of travellers recommend
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
