Hillside Holidays from AU$963
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Your Hillside Holiday
The stress-free way to experience this interesting city is with a tailor-made Hillside holiday package. Base yourself in the neighbourhood of Wicker Park, which is great for nightlife, bars and pubs and cafes or go someplace else — our packages are all about you. Any trip to Hillside needs a well-planned itinerary. Fill yours with famous sights like Brookfield Zoo, Oakbrook Centre Mall and Ernest Hemingway Museum and House. Don't delay your visit to this destination any longer. Your perfect Hillside holiday is a few clicks away with Expedia.
The Latest Hillside Holiday Deals
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was AU$1,181, price is now AU$963 per person
AU$963
per person
23 Dec - 26 Dec
found 1 day ago
Return direct flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
Clean room, friendly staff, great location and within walking distance from all shops!
Reviewed on 7 Oct 2025
Pendry Chicago
Downtown Chicago
Price was AU$1,361, price is now AU$1,027 per person
AU$1,027
per person
23 Dec - 26 Dec
found 1 day ago
Return direct flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
I loved the hotel, however I would request an inside room next time. It was extremely noisy outside.
Reviewed on 11 Oct 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was AU$1,295, price is now AU$977 per person
AU$977
per person
23 Dec - 26 Dec
found 1 day ago
Return direct flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (291 reviews)
Food price was high but everything was fine
Reviewed on 4 Oct 2025
Swissotel - Chicago
Downtown Chicago
Price was AU$1,263, price is now AU$971 per person
AU$971
per person
23 Dec - 26 Dec
found 1 day ago
Return direct flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (2,765 reviews)
The view from the panoramic view was amazing. The gym was comfortable and the credit to amuse was nice
Reviewed on 9 Oct 2025
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was AU$1,290, price is now AU$1,062 per person
AU$1,062
per person
23 Dec - 26 Dec
found 1 day ago
Return direct flight included
Calgary (YYC) to Chicago (ORD)
8.6/10 Excellent! (1,920 reviews)
Fabulous suite overlooking Millenium Park and Lake Michigan. Clean, attentive staff, and good amenities. Walk to everything.
Reviewed on 10 Oct 2025
Hillside Holiday
Hillside Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Population | 8,200 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 27ºC |
Top Sights | Rosemont Theatre, Brookfield Zoo and Parkway Bank Park Entertainment District |
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 AU$305 per night from 26 Oct to 27 Oct
AU$305
26 Oct - 27 Oct
includes taxes & fees
8/10 Very Good! (9,333 reviews)
"Very clean"
Reviewed on 7 Oct 2025
Freehand Chicago
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$149 per night from 12 Nov to 13 Nov
AU$149
12 Nov - 13 Nov
includes taxes & fees
7.8/10 Good! (2,425 reviews)
"Excellent location, clean and good room partners"
Reviewed on 6 Oct 2025
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$276 per night from 9 Nov to 10 Nov
AU$276
9 Nov - 10 Nov
includes taxes & fees
8.4/10 Very Good! (5,052 reviews)
"good"
Reviewed on 7 Oct 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
Navy Pier
4.5/5(64 reviews)
A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.
Millennium Park
4.5/5(73 reviews)
One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.
Grant Park
4.5/5(47 reviews)
Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.
What to do in Hillside
Skydeck - Willis Tower Admission
AU$67
per adult
100% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
AU$37
per adult
84% of travellers recommend
Explore a world of travel with Expedia
Lodging
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- Apartments in Villa Park
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- B&B in Western Springs
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Packages
- Apache Park
- Austin Holidays
- Berkeley Holidays
- Busy Beaver Button Museum
- Chicago Holidays
- Daley Plaza
- Elk Grove Village Holidays
- Emily Oaks Nature Center
- Frank Lloyd Wright Historic District
- Visit Franklin Park
- Garfield Park Conservatory
- Golf Holidays
- Grace Abbott Homes Holidays
- Hanson Park
- Legoland® Discovery Center
- Lincoln Hall
- Lincoln Park Conservatory
- Lombard Holidays
- Visit Melrose Park
- Morton Arboretum
- Oak Lawn Holidays
- Rainbow Falls Waterpark
- Riverside Holidays
- Rookery
- Rosemont Theatre
- Rosemont Holidays
- Summit Holidays
- United Center
- Unity Temple
- University of Illinois Chicago
- Wicker Park Holidays
- Willis Tower
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
