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Hillside Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Hillside

Business center
Kasa River North Chicago

Kasa River North Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (180)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Front of property - evening/night
Level Chicago – Old Town

Level Chicago – Old Town

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (391)
"Clean room cool staff enjoyed my stay will come stay again. "
United States
Donald
Level Chicago – Old Town
Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (997)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is ￥15,738
￥23,058 total
includes taxes & fees
Dec 7 - Dec 8
Sentral Michigan Avenue
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space

Downtown Chicago
9.6 out of 10, Exceptional, (14)
"Host was easy to communicate with and very thoughtful. We were in town for a concert and they gifted us with ear protection for us all. Location was great too "
United States
Tiffany N.
The price is ￥9,683
￥28,473 total
includes taxes & fees
Dec 7 - Dec 8
Twice as Nice: Chic 2BR Stay with Style & Space
Fridge, microwave, oven, stovetop
Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment

Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is ￥8,590
￥24,850 total
includes taxes & fees
Dec 4 - Dec 5
Sun-Drenched 1BR Apartment
Fridge, microwave, oven, stovetop
West Loop Living – Bright 1BR

West Loop Living – Bright 1BR

Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Pretty cool place to stay for a short trip ! Everything was close to where we were which made traveling a lot easier. Apartment is a pretty decent size I would recommend just 2-3 people. You can easily contact the host about anything and they’ll respond within a timely manner. The only down side of this place was the shower cleanliness itself. Overall, cool place not bad at all definitely a quick trip kind of thing!"
United States
Majanique M.
The price is ￥8,590
￥24,850 total
includes taxes & fees
Dec 7 - Dec 8
West Loop Living – Bright 1BR
Fridge, microwave, oven, stovetop
Stylish 1BR in West Loop

Stylish 1BR in West Loop

Downtown Chicago
10.0 out of 10, Exceptional, (10)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
United States
Jacob D.
The price is ￥9,839
￥26,313 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Stylish 1BR in West Loop
Fridge, microwave, oven, stovetop
The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home

Downtown Chicago
9.6 out of 10, Exceptional, (4)
"Convenient location and clean place"
United States
David S.
The price is ￥8,590
￥24,850 total
includes taxes & fees
Dec 3 - Dec 4
The One: A 1BR Stay That Feels Like Home
Interior
Gold Coast Living: Modern Studio Unit

Gold Coast Living: Modern Studio Unit

Downtown Chicago
10.0 out of 10, Exceptional, (4)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is ￥10,776
￥25,849 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Gold Coast Living: Modern Studio Unit
Interior
Your Chicago get Away

Your Chicago get Away

Downtown Chicago
8.4 out of 10, Very Good, (8)
"Clean, fun space and responsive host! Loved the views from our room!"
United States
Tyler C.
The price is ￥27,550
￥59,269 total
includes taxes & fees
Dec 2 - Dec 3
Your Chicago get Away
Fridge, microwave, oven, stovetop
River North Rooftop With In and Out Parking 1

River North Rooftop With In and Out Parking 1

Downtown Chicago
9.0 out of 10, Wonderful, (2)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
The price is ￥16,243
￥49,400 total
includes taxes & fees
Dec 7 - Dec 8
River North Rooftop With In and Out Parking 1
1 bedroom, WiFi, bed sheets
1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry

Downtown Chicago
10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is ￥9,839
￥26,313 total
includes taxes & fees
Jan 1 - Jan 2, 2026
1BR Modern Luxe Apt with In-Unit Laundry
Free WiFi, bed sheets
Chicago luxury home suites

Chicago luxury home suites

2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job."
Canada
pouya
The price is ￥39,744
￥46,654 total
includes taxes & fees
Dec 2 - Dec 3
Chicago luxury home suites
4 bedrooms, iron/ironing board, travel crib, WiFi
Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3

2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"The host communicated everything very well. The short videos sent giving info about all the things you'd need to know were super helpful!"
United States
Laurie A.
The price is ￥22,990
￥30,718 total
includes taxes & fees
Dec 30 - Dec 31
Modern West Loop Gem-City Views & Prime Location 3
Fridge, microwave, oven, stovetop
South Loop Rooftop With In and Out Parking 3

South Loop Rooftop With In and Out Parking 3

Downtown Chicago
8.6 out of 10, Excellent, (4)
"Modern and stylish apartment in a great location. Lots of extra thoughtful touches made it a great stay. "
Australia
Angela M.
The price is ￥30,299
￥67,053 total
includes taxes & fees
Dec 19 - Dec 20
South Loop Rooftop With In and Out Parking 3
TV, offices
Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ Laundry

Downtown Chicago
10.0 out of 10, Exceptional, (1)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveler
The price is ￥8,590
￥24,850 total
includes taxes & fees
Dec 2 - Dec 3
Sleek 1BR Apt w/ Laundry
Iron/ironing board, travel crib, WiFi, bed sheets
Modern Studio Near UChicago

Modern Studio Near UChicago

Hyde Park
9.4 out of 10, Exceptional, (10)
"Clean room and convenient location! "
United States
Gabriela
The price is ￥9,371
￥24,202 total
includes taxes & fees
Dec 7 - Dec 8
Modern Studio Near UChicago
Private kitchen
Spacious 3-bedroom apartment near downtown, FREE PARKING

Spacious 3-bedroom apartment near downtown, FREE PARKING

Near West Side
9.4 out of 10, Exceptional, (8)
"Nice place to stay. Good communication with the owner."
United States
Ryan
The price is ￥9,058
￥51,837 total
includes taxes & fees
Dec 2 - Dec 3
Spacious 3-bedroom apartment near downtown, FREE PARKING
Studio | Exterior
Chicago Third Floor Studio by 747 Lofts

Chicago Third Floor Studio by 747 Lofts

2.0 star property
West Town
9.6 out of 10, Exceptional, (5)
"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 ￥9,254
￥34,149 total
includes taxes & fees
Dec 3 - Dec 4
Chicago Third Floor Studio by 747 Lofts
Fridge, microwave, oven, stovetop
Beautifully Set Up 2BR Space

Beautifully Set Up 2BR Space

Lakeview
9.6 out of 10, Exceptional, (20)
"The apartment worked out perfectly for our stay. Very good location for our activities and comfortable for just hanging out."
United States
Linda S.
The price is ￥9,683
￥28,473 total
includes taxes & fees
Dec 2 - Dec 3
Beautifully Set Up 2BR Space
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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Superb service at the hotel staff "
Michael 1-night trip
Posted 2 hours ago
Hilton Chicago/Magnificent Mile Suites

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:

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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 vacation rental in Hillside?

Yes, you can find vacation rentals near popular sights in Hillside, or you can choose a secluded option if you're looking for relaxation. Visitors like the top-notch restaurants and forests in Hillside. Allow some time to check out the shops during your trip.

What are some of the best vacation rentals that Hillside has to offer?

LakeHouse: This vacation home rental outside of Hillside is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 vacation rentals like in Hillside?

Vacation rentals are privately owned accommodations you can reserve for several days or more in Hillside. Vacation rentals offer extras such as laundry facilities and kitchens so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for a small group gathering.