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Check prices for these dates

Tonight
24 Dec - 25 Dec
Tomorrow
25 Dec - 26 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Hillside holiday rentals

Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1020)
"This place made a great landing spot for a holiday weekend w family. Clean, great location, loved the holiday decorations and indoor pool / outside hot tub. Will stay again! "
United States
Deidre
The price is ฿3,675
฿5,228 total
includes taxes & fees
4 Jan - 5 Jan 2026
Sentral Michigan Avenue
Business centre
Kasa River North Chicago

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Front of property
Chicago luxury home suites

Aparthotel in Downtown Chicago

Chicago luxury home suites
2.0 star property
8.4 out of 10, Very good, (5)
"Amazing stay! The location is very central and close to everything. The room was spotless, and the mattress was very comfortable. I really appreciated that the property is pet friendly. I was able to bring my dog along, which made the trip even better. The view was absolutely stunning. The hosts were very responsive and helpful throughout our stay. Highly recommend!"
Canada
Alex
The price is ฿4,199
฿4,930 total
includes taxes & fees
28 Dec - 29 Dec
Chicago luxury home suites
Front of property – evening/night
Level Chicago – Old Town

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (404)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
Studio | Exterior
Chicago Third Floor Studio by 747 Lofts

Aparthotel in West Town

Chicago Third Floor Studio by 747 Lofts
2.0 star property
9.8 out of 10, Exceptional, (6)
"Cute little studio that was clean. There was a nice size kitchen and was close to our activities in the West loop of Chicago. There was also assistance with parking located in the lofts."
United States
Jennifer
The price is ฿2,158
฿7,223 total
includes taxes & fees
30 Dec - 31 Dec
Chicago Third Floor Studio by 747 Lofts
Living area
Wrigleyville Suites

Aparthotel in Lakeview

Wrigleyville Suites
2.0 star property
9.6 out of 10, Exceptional, (26)
"Excellent location and very clean! Would stay again!"
United States
Jacob
The price is ฿2,772
฿3,254 total
includes taxes & fees
25 Dec - 26 Dec
Wrigleyville Suites
Suite, 2 Bedrooms, Kitchen (Three Beds, Washer/Dryer) | Private kitchen | Full-sized fridge, microwave, stovetop, dishwasher
The Gem Museum Suites

Aparthotel in Downtown Evanston

The Gem Museum Suites
3.5 star property
9.4 out of 10, Exceptional, (99)
"Great stay. The studio is small but has everything necessary."
United States
Julia
The price is ฿5,655
฿6,474 total
includes taxes & fees
7 Jan - 8 Jan 2026
The Gem Museum Suites
House (3 Bedrooms) | Interior
Classic Forest Park Foursquare < 1 Mi to Blue Line

Cottage in Forest Park

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
The price is ฿4,915
฿12,831 total
includes taxes & fees
1 Jan - 2 Jan 2026
Classic Forest Park Foursquare < 1 Mi to Blue Line
Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior
Historic Oak Park Residence

Apartment in Oak Park

Historic Oak Park Residence
2.0 star property
9.6 out of 10, Exceptional, (12)
"Absolutely awesome "
United States
Erik
Historic Oak Park Residence
Studio | Exterior
Cabin 105 by 747 Lofts

Aparthotel in West Town

Cabin 105 by 747 Lofts
2.0 star property
10.0 out of 10, Exceptional, (1)
The price is ฿1,843
฿4,170 total
includes taxes & fees
30 Dec - 31 Dec
Cabin 105 by 747 Lofts
Design Apartment, Private Bathroom (The Oak Park Loft) | View from property
The Oak Park Loft

Apartment in Oak Park

The Oak Park Loft
2.0 star property
10.0 out of 10, Exceptional, (5)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is ฿6,579
฿10,986 total
includes taxes & fees
25 Dec - 26 Dec
The Oak Park Loft
Studio | Exterior
River West, Second Floor Chicago by 747 Lofts

Aparthotel in West Town

River West, Second Floor Chicago by 747 Lofts
2.0 star property
9.6 out of 10, Exceptional, (4)
"I need to somewhere to stay for a night in Chicago and found this place. It had a varying level of reviews but found the property more the suitable for what I paid. Easy to follow instructions to get in, clean, and convienent. They even provide ear plugs to drown out the sounds of the city."
United States
Anonymous traveller
The price is ฿2,000
฿7,012 total
includes taxes & fees
1 Jan - 2 Jan 2026
River West, Second Floor Chicago by 747 Lofts
Studio | Private kitchen | Fridge, oven, coffee/tea maker, toaster
Chicago Second Floor Studio by 747 Lofts

Aparthotel in West Town

Chicago Second Floor Studio by 747 Lofts
2.0 star property
8.8 out of 10, Excellent, (13)
"Great location, convenient to downtown and blue line to airport. Everything necessary in unit, comfortable temperature and full kitchen with unique grocery store nearby."
United States
Barbara
The price is ฿2,063
฿4,464 total
includes taxes & fees
28 Dec - 29 Dec
Chicago Second Floor Studio by 747 Lofts
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.
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Top Hillside Hotel Reviews

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent
"I prefer Embassy Suite over any hotel. ES does not fail in quality, comfort, cleanliness. We enjoyed Chicago very much. Embassy Suite was in walking distance. Staff were very friendly. "
Chastity 3-night trip
Posted 9 hours ago
Embassy Suites by Hilton Chicago Downtown River North

Find out more about Hillside

Search for holiday rentals in Hillside on Expedia! You can easily find your home rentals, villas, holiday apartments in Hillside using one of the methods below:

  • View our selection of featured holiday rentals in Hillside
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Look no further and take a look at our great range of rental properties in Hillside!

Frequently asked questions

Can I find a holiday rental in Hillside?

Yes, there are holiday rentals close to the most popular sights in Hillside, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and forests in Hillside. Allow some time to check out the shops during your trip.

What can I see and do in Hillside?

Enjoy the area's cultural attractions such as Drury Lane Theater, or get outdoors into nature at a spot like Millennium Park. Other popular places to visit in the area include Wrigley Field and Michigan Avenue.

What are holiday rentals like in Hillside?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Hillside. Holiday rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a family trip or a small group gathering.