Title: Hillside Vacation Rentals from CA $177: Short-Term Rentals for 2026 | Expedia.ca

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## Check prices for these dates

In two weeks

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=8353&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=8353&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=8353&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=8353&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Hillside vacation rentals

![Indoor pool](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/58291697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/ccaab668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Apartment, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/ecc0a878.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Apartment, 1 Bedroom | Private kitchen](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/f6d9d5c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sentral Michigan Avenue

[](https://www.expedia.ca/Chicago-Hotels-Sentral-Michigan-Avenue.h76267438.Hotel-Information)

Downtown Chicago

9.2/10

Wonderful

(1,069 reviews)

"Best full kitchen multi-room family lodging"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lee

CA $150

CA $216 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Chicago-Hotels-Sentral-Michigan-Avenue.h76267438.Hotel-Information)

![Lounge](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/0480d64e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 10:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/88e54d1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/f7e5c565_edited_04eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Signature Apartment, 1 King Bed with Sofa bed, Pool Access (Self Check-in with Virtual Front Desk) | Living area](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/2969f0ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kasa River North Chicago

[](https://www.expedia.ca/Chicago-Hotels-Kasa-River-North-Chicago.h66425311.Hotel-Information)

Downtown Chicago

9.6/10

Exceptional

(183 reviews)

"Awesome stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sally

[](https://www.expedia.ca/Chicago-Hotels-Kasa-River-North-Chicago.h66425311.Hotel-Information)

![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8c061e2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/d03e88da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 1 Single Bed, City View | Living area](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/f7ca0ea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, pillowtop beds, in-room safe, individually decorated](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/4a3a770c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Level Chicago – Old Town

[](https://www.expedia.ca/Chicago-Hotels-LEVEL-Furnished-Living-Chicago.h39805843.Hotel-Information)

Downtown Chicago

9.0/10

Wonderful

(421 reviews)

"Clean, nice amenities and great staff."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sydnee

CA $265

CA $345 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Chicago-Hotels-LEVEL-Furnished-Living-Chicago.h39805843.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/3e1fd538.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/3935f43c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/3e6dada5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/7b407b40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wrigleyville Suites

[](https://www.expedia.ca/Chicago-Hotels-Wrigleyville-Suites.h104315648.Hotel-Information)

Lakeview

9.2/10

Wonderful

(29 reviews)

"Nice place "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Barry

CA $162

CA $191 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Chicago-Hotels-Wrigleyville-Suites.h104315648.Hotel-Information)

![Apartment, Private Bathroom | Lounge](https://images.trvl-media.com/lodging/76000000/75610000/75609600/75609586/75db7b4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/76000000/75610000/75609600/75609586/a3594234.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, Private Bathroom | Terrace/patio](https://images.trvl-media.com/lodging/76000000/75610000/75609600/75609586/2e2b5c00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, Private Bathroom | Interior](https://images.trvl-media.com/lodging/76000000/75610000/75609600/75609586/d23bf6a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### At Home in Oak Park

[](https://www.expedia.ca/Chicago-Hotels-Home-In-Oak-Park.h75609586.Hotel-Information)

Oak Park

9.4/10

Exceptional

(9 reviews)

"Great location in Oak Park- walkable, wondering area for restaurants and strolling through the beautiful neighborhoods."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kathryn

CA $174

CA $351 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Chicago-Hotels-Home-In-Oak-Park.h75609586.Hotel-Information)

![Breakfast, lunch, dinner served; Greek cuisine ](https://images.trvl-media.com/lodging/104000000/103470000/103465500/103465448/424c972a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/104000000/103470000/103465500/103465448/9897f375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103470000/103465500/103465448/3102ad4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/104000000/103470000/103465500/103465448/c54d2fb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Gem Museum Suites

[](https://www.expedia.ca/Chicago-Hotels-The-Gem-Museum-Suites.h103465448.Hotel-Information)

Downtown Evanston

9.4/10

Exceptional

(104 reviews)

"This is a fantastic hotel with super friendly staff"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

German

CA $247

CA $283 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Chicago-Hotels-The-Gem-Museum-Suites.h103465448.Hotel-Information)

![Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Lounge](https://images.trvl-media.com/lodging/89000000/88180000/88173500/88173402/8abcd27a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/89000000/88180000/88173500/88173402/a6832f09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Interior](https://images.trvl-media.com/lodging/89000000/88180000/88173500/88173402/7547fb3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/89000000/88180000/88173500/88173402/df6e2a2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Oak Park Home

[](https://www.expedia.ca/Chicago-Hotels-Historic-Oak-Park-Home.h88173402.Hotel-Information)

Oak Park

10/10

Exceptional

(5 reviews)

"Wanted a house in oak park and this was such a pleasant, comfortable and convenient place. Really comfortable beds too. Even a lovely piano. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

judith

CA $164

CA $340 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Chicago-Hotels-Historic-Oak-Park-Home.h88173402.Hotel-Information)

![Dining room](https://images.trvl-media.com/lodging/47000000/46240000/46231100/46231022/264e98f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/47000000/46240000/46231100/46231022/b5ecc9d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/47000000/46240000/46231100/46231022/a150e313.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Studio, 1 Queen Bed with Sofa bed, Non Smoking (Self Check-in with Virtual Front Desk)](https://images.trvl-media.com/lodging/47000000/46240000/46231100/46231022/5de126ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kasa Magnificent Mile Chicago

[](https://www.expedia.ca/Chicago-Hotels-Kasa-Chicago-River-North-Apartments.h46231022.Hotel-Information)

Downtown Chicago

9.4/10

Exceptional

(687 reviews)

"Perfect location and very clean! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Latoya

CA $195

CA $310 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Chicago-Hotels-Kasa-Chicago-River-North-Apartments.h46231022.Hotel-Information)

![Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior](https://images.trvl-media.com/lodging/95000000/94680000/94670100/94670079/9b9f65df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior](https://images.trvl-media.com/lodging/95000000/94680000/94670100/94670079/3a1a2525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exclusive Room, Private Bathroom, Garden View (2nd Floor)](https://images.trvl-media.com/lodging/95000000/94680000/94670100/94670079/5beac5cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Lounge](https://images.trvl-media.com/lodging/95000000/94680000/94670100/94670079/13874d20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Oak Park Residence

[](https://www.expedia.ca/Chicago-Hotels-Historic-Oak-Park-Residence.h94670079.Hotel-Information)

Oak Park

9.6/10

Exceptional

(12 reviews)

"Absolutely awesome "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Erik

CA $165

CA $341 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Chicago-Hotels-Historic-Oak-Park-Residence.h94670079.Hotel-Information)

![Design Apartment, Private Bathroom (The Oak Park Loft)](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/dfb80f4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Design Apartment, Private Bathroom (The Oak Park Loft)](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/515455d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/167883c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Design Apartment, Private Bathroom (The Oak Park Loft) | Exterior](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/733d465a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Oak Park Loft

[](https://www.expedia.ca/Chicago-Hotels-The-Oak-Park-Loft.h107622605.Hotel-Information)

Oak Park

10/10

Exceptional

(5 reviews)

"Good location, nice neighborhood, restaurants close"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Linda

CA $153

CA $327 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Chicago-Hotels-The-Oak-Park-Loft.h107622605.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-21&endDate=2026-02-22&regionId=8353&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Hillside%2C+Illinois%2C+United+States+of+America&regionId=8353&latLong=41.877808%2C-87.90284&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Hillside%2C+Illinois%2C+United+States+of+America&regionId=8353&latLong=41.877808%2C-87.90284&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=APARTMENT)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Hillside%2C+Illinois%2C+United+States+of+America&regionId=8353&latLong=41.877808%2C-87.90284&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=VACATION_HOME)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Hillside%2C+Illinois%2C+United+States+of+America&regionId=8353&latLong=41.877808%2C-87.90284&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=CONDO)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Hillside%2C+Illinois%2C+United+States+of+America&regionId=8353&latLong=41.877808%2C-87.90284&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=VILLA)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Hillside%2C+Illinois%2C+United+States+of+America&regionId=8353&latLong=41.877808%2C-87.90284&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=COTTAGE)

Residences

[](https://www.expedia.ca/Hotel-Search?destination=Hillside%2C+Illinois%2C+United+States+of+America&regionId=8353&latLong=41.877808%2C-87.90284&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=RESIDENCE)

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## Top Hillside Hotel Reviews

![DoubleTree by Hilton Chicago - Magnificent Mile](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e_y.jpg)

### DoubleTree by Hilton Chicago - Magnificent Mile

10/10 Excellent

"Awesome quite hotel beds are amazing great location "

[](https://expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information)

![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg)

### Sable at Navy Pier Chicago, Curio Collection by Hilton

10/10 Excellent

"Very clean and friendly staff"

[](https://expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information)

![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/74c2f40d_y.jpg)

### LondonHouse Chicago, Curio Collection by Hilton

10/10 Excellent

"Everything was amazing! View ambience service "

[](https://expedia.ca/Chicago-Hotels-LondonHouse-Chicago.h12786616.Hotel-Information)

![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982_y.jpg)

### Eurostars Magnificent Mile

10/10 Excellent

"Room was great! We even got upgraded to a deluxe room. Staff cleaned the room almost everyday we stayed and they brought us as much tea and coffee as we wanted. Only thing I’m not pleased about is the lack of a microwave in the unit. A believe only the suites have a microwave but we made it work. The hotel staff was lovely and the cafe down stairs had great food. 10/10 experience, will definitely be back soon."

[](https://expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information)

![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg)

### Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent

"Yes room was spotless "

[](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information)

![Aloft Chicago Mag Mile](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/d755f57e_y.jpg)

### Aloft Chicago Mag Mile

10/10 Excellent

"it was good"

[](https://expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information)

![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg)

### Hyatt Regency Chicago

10/10 Excellent

"Clean room, professional staff, and great location"

[](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information)

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg)

### Hotel Riu Plaza Chicago

10/10 Excellent

"Nice"

[](https://expedia.ca/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information)

![Courtyard by Marriott Chicago Magnificent Mile](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/529d8be8_y.jpg)

### Courtyard by Marriott Chicago Magnificent Mile

10/10 Excellent

"I had a beautiful stay at Courtyard Marriot/MM Chicago. The room was clean, staff courteous and accommodating. The amenities were excellent. Shout out to bartender, Leo at GastoPub!!💕💕 I would most definitely book here again!!"

[](https://expedia.ca/Chicago-Hotels-Courtyard-By-Marriott-Chicago-Magnificent-Mile.h982517.Hotel-Information)

## Find out more about Hillside

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Hillside. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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