Title: Hillside Vacation Rentals from $106: Search Short-Term Rentals | Expedia.com

[Hillside Travel Guide](https://expedia.com/Hillside.dx8353)[Hotels in Hillside](https://expedia.com/Hillside-Hotels.d8353.Travel-Guide-Hotels)[Flights to Hillside](https://expedia.com/Cheap-Flights-To-Hillside.d8353.Travel-Guide-Flights)[Car Rentals in Hillside](https://expedia.com/Car-Rentals-In-Hillside.d8353.Car-Rental-Guide)[Hillside Vacation Packages](https://expedia.com/Hillside.d8353.Destination-Travel-Guides)

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## Check prices for these dates

In two weeks

[Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=8353&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=8353&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=8353&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=8353&startDate=2026-06-19&endDate=2026-06-21&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

![Interior](https://images.trvl-media.com/lodging/118000000/117520000/117515200/117515137/d8e9b0e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117520000/117515200/117515137/a410264a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/118000000/117520000/117515200/117515137/6c271db9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117520000/117515200/117515137/57a172f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### River North Rooftop With In and Out Parking 3

[](https://www.expedia.com/Chicago-Hotels-River-North-Rooftop-With-In-Out-Parking-3.h117515137.Hotel-Information)

Downtown Chicago

9.6/10

Exceptional

(4 reviews)

"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"

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

Jennifer M.

$345 nightly

$391 total

Mar 10 - Mar 11

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-River-North-Rooftop-With-In-Out-Parking-3.h117515137.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/w1532h1024x4y0-bf7afd3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/31b5d53e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/65e9350a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/c8b54872.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sleek 1BR Apartment w/ In-unit Laundry

[](https://www.expedia.com/Chicago-Hotels-Sleek-1BR-Apt-W-Laundry.h116793107.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(1 review)

"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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anonymous traveler

$217 nightly

$243 total

Mar 23 - Mar 24

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Sleek-1BR-Apt-W-Laundry.h116793107.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/7d7ccc69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/93c17f93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/c6bb5c1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/a49da56a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sun-Drenched 1BR Apartment

[](https://www.expedia.com/Chicago-Hotels-Sun-Drenched-1BR-Apartment.h116792936.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(2 reviews)

"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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tyler B.

$203 nightly

$227 total

Mar 9 - Mar 10

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Sun-Drenched-1BR-Apartment.h116792936.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/afe63d9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/143f3ef1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/19144195.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/8ec83200.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Comfort: 1BR Unit w/ Laundry

[](https://www.expedia.com/Chicago-Hotels-Stylish-1BR-In-West-Loop.h116793043.Hotel-Information)

Downtown Chicago

9.2/10

Wonderful

(15 reviews)

"Great host comfortable bed close to restaurants and parks"

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

Alana C.

$206 nightly

$231 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Stylish-1BR-In-West-Loop.h116793043.Hotel-Information)

![Desk, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/7a65e5d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/1c0ee66d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/f0a938f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/b5bee4f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chic Studio in the Heart of the Gold Coast

[](https://www.expedia.com/Chicago-Hotels-Cozy-Gold-Coast-Studio-Stay.h120508888.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(5 reviews)

"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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Seynabou

$195 nightly

$220 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Cozy-Gold-Coast-Studio-Stay.h120508888.Hotel-Information)

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/b10cb31b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/368bd483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/b754723c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/4fcb7f04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### West Loop Living – Bright 1BR

[](https://www.expedia.com/Chicago-Hotels-West-Loop-Living-Bright-1BR.h119131874.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(7 reviews)

"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."

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

Jeffrey

$206 nightly

$231 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-West-Loop-Living-Bright-1BR.h119131874.Hotel-Information)

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

![Premium Apartment, 2 Bedrooms | Private kitchen | Oven, stovetop, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/83f39cf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Apartment, 2 Bedrooms | Living area | 55-inch flat-screen TV with cable channels, TV](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 | Oven, stovetop, dishwasher, coffee/tea maker](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.com/Chicago-Hotels-Sentral-Michigan-Avenue.h76267438.Hotel-Information)

Downtown Chicago

9.2/10

Wonderful

(1,096 reviews)

"Best full kitchen multi-room family lodging"

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

Lee

$135 nightly

$158 total

Mar 2 - Mar 3

Total with taxes and fees

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

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/e255803d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/96789a75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/fe11ac9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/4b4ff505.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1BR Modern Luxe Apt with In-Unit Laundry

[](https://www.expedia.com/Chicago-Hotels-1BR-Modern-Luxe-Apt-With-In-Unit-Laundry.h119131871.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(1 review)

"Great experience for me and my wife I would definitely come back "

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

ShowtimeFam1

$206 nightly

$231 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-1BR-Modern-Luxe-Apt-With-In-Unit-Laundry.h119131871.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/w953h720x163y0-0c76a558.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/64fce148.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/699e81d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/cf096b64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### A quiet stay while you are away

[](https://www.expedia.com/Chicago-Hotels-A-Quiet-Stay-While-You-Are-Away.h49092456.Hotel-Information)

Oak Park

9.8/10

Exceptional

(34 reviews)

"Everything was very comfortable and Jay did a great job of showing the house. I would definitely come back again"

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

Fred D.

$181 nightly

$207 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-A-Quiet-Stay-While-You-Are-Away.h49092456.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/7b6dc406.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/932d3e6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/5569ce20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/c1640248.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### \*The Comfy King Ranch\*King Bed Suite\*Fast Wi-Fi

[](https://www.expedia.com/Chicago-Hotels-The-Comfy-King-Ranch-King-BedFast-WiFiFree-Pkg.h71677273.Hotel-Information)

Worth

9.4/10

Exceptional

(57 reviews)

"Very clean and comfortable! Great place for our short stay! So much space it was great!"

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

David L.

$311 nightly

$332 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-The-Comfy-King-Ranch-King-BedFast-WiFiFree-Pkg.h71677273.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/123000000/122120000/122119700/122119695/8e2390b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122120000/122119700/122119695/f0acbbba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/123000000/122120000/122119700/122119695/85daceee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122120000/122119700/122119695/w4032h2772x0y0-82beddf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

[](https://www.expedia.com/Chicago-Hotels-Cozy-Garden-Suite-Minutes-From-Ohare-And-Rosemont-Free-Parking.h122119695.Hotel-Information)

Northlake

10/10

Exceptional

(4 reviews)

"Had a great experience here, and also close to the airport!"

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

Yafeat D.

$115 nightly

$123 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Cozy-Garden-Suite-Minutes-From-Ohare-And-Rosemont-Free-Parking.h122119695.Hotel-Information)

![Design Apartment, Private Bathroom (The Oak Park Loft) | 2 bedrooms](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) | 2 bedrooms](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/515455d8.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)

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

### The Oak Park Loft

[](https://www.expedia.com/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

$237 nightly

$271 total

Mar 2 - Mar 3

Total with taxes and fees

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

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793099/bc53e5ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793099/f308661a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793099/253117f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793099/f18cb47c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Sunlit 1BR Apartment

[](https://www.expedia.com/Chicago-Hotels-Prime-City-Stay-In-A-1BR-Apt.h116793099.Hotel-Information)

Irving Park

9.2/10

Wonderful

(12 reviews)

"Host was very attentive and answered all of our questions. It was very cozy and exactly as pictured."

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

Brandon M.

$159 nightly

$176 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Prime-City-Stay-In-A-1BR-Apt.h116793099.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 | 55-inch flat-screen TV with digital channels, TV](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.com/Chicago-Hotels-Kasa-River-North-Chicago.h66425311.Hotel-Information)

Downtown Chicago

9.4/10

Exceptional

(184 reviews)

"Awesome stay "

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

Sally

$234 nightly

$275 total

Mar 8 - Mar 9

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/100000000/99670000/99665400/99665339/w904h683x60y0-0a03c909.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99670000/99665400/99665339/w904h683x60y0-fd8eb476.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/100000000/99670000/99665400/99665339/w908h683x58y0-c6e60f75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99670000/99665400/99665339/w438h683x287y0-7bc85031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Oak Park Queen

[](https://www.expedia.com/Chicago-Hotels-Oak-Park-Queen.h99665339.Hotel-Information)

Oak Park

8.2/10

Very Good

(32 reviews)

"The property was very clean and comfortable. Good location. The owner was responsive."

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

Susan S.

$196 nightly

$224 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Oak-Park-Queen.h99665339.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95140000/95134600/95134539/b80be72b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/96000000/95140000/95134600/95134539/w903h683x60y0-a4b1b07a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/96000000/95140000/95134600/95134539/w906h683x59y0-ad8ac03d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/96000000/95140000/95134600/95134539/w905h683x60y0-4a286511.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

[](https://www.expedia.com/Chicago-Hotels-PROMO-10WEEKLY-12-MONTHLY-DISCJacuzzi.h95134539.Hotel-Information)

Westchester

9.8/10

Exceptional

(20 reviews)

"Great place Great location "

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

Josh W.

$442 nightly

$473 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-PROMO-10WEEKLY-12-MONTHLY-DISCJacuzzi.h95134539.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/72000000/71470000/71469600/71469533/d71c19e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/72000000/71470000/71469600/71469533/w640h303x0y0-b3048deb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/72000000/71470000/71469600/71469533/0db05817.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/72000000/71470000/71469600/71469533/dc065fc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish Luxe King bed w/Free Parkng near DT Oak Pk

[](https://www.expedia.com/Chicago-Hotels-Stylish-2BDR.h71469533.Hotel-Information)

Oak Park

9.6/10

Exceptional

(98 reviews)

"Cozy place, host was very helpful and responded quickly to all my concerns. I would definitely stay there again. "

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

Deborah R.

$248 nightly

$283 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Stylish-2BDR.h71469533.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)

![Deluxe Room, 1 Twin Bed, City View | Living area | Flat-screen TV](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/f7ca0ea3.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)

![Front of property - evening/night](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Level Chicago – Old Town

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

Downtown Chicago

9.0/10

Wonderful

(435 reviews)

"Clean, nice amenities and great staff."

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

Sydnee

$213 nightly

$250 total

Mar 3 - Mar 4

Total with taxes and fees

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

![Property grounds](https://images.trvl-media.com/lodging/104000000/103750000/103740100/103740087/e540979f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/104000000/103750000/103740100/103740087/14dd3707.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103750000/103740100/103740087/60302aec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103750000/103740100/103740087/699c0a64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pet Friendly-Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum

[](https://www.expedia.com/Chicago-Hotels-Pet-Friendly-Studio-Apartment-Three-Blocks-From-Train-To-Downtown-Chicago.h103740087.Hotel-Information)

Downers Grove

9.6/10

Exceptional

(31 reviews)

"Great option for a relatively affordable place to stay near family."

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

Erick B.

$118 nightly

$125 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Pet-Friendly-Studio-Apartment-Three-Blocks-From-Train-To-Downtown-Chicago.h103740087.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792932/9b3edef7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792932/90117668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792932/7d8930ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792932/cffd5d1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ideal 2BR Getaway Close to Attractions

[](https://www.expedia.com/Chicago-Hotels-Spacious-2BR-Near-Dining-Shops.h116792932.Hotel-Information)

Rogers Park

8.4/10

Very Good

(7 reviews)

"Loved this sweet space tucked into a special neighborhood in the city. Space was clean & comfortable, wonderful shower & a nice respite from city life. "

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

Ever

$194 nightly

$214 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Spacious-2BR-Near-Dining-Shops.h116792932.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.com/Hotel-Search?startDate=2026-03-15&endDate=2026-03-16&regionId=8353&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

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## Find vacation rentals that suit your style

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Hillside%2C+Illinois%2C+United+States+of+America&regionId=8353&latLong=41.877808%2C-87.90284&adults=2&startDate=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Hillside%2C+Illinois%2C+United+States+of+America&regionId=8353&latLong=41.877808%2C-87.90284&adults=2&startDate=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=APARTMENT)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Hillside%2C+Illinois%2C+United+States+of+America&regionId=8353&latLong=41.877808%2C-87.90284&adults=2&startDate=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=VACATION_HOME)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Hillside%2C+Illinois%2C+United+States+of+America&regionId=8353&latLong=41.877808%2C-87.90284&adults=2&startDate=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=CONDO)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Hillside%2C+Illinois%2C+United+States+of+America&regionId=8353&latLong=41.877808%2C-87.90284&adults=2&startDate=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=VILLA)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Hillside%2C+Illinois%2C+United+States+of+America&regionId=8353&latLong=41.877808%2C-87.90284&adults=2&startDate=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=COTTAGE)

Residences

[](https://www.expedia.com/Hotel-Search?destination=Hillside%2C+Illinois%2C+United+States+of+America&regionId=8353&latLong=41.877808%2C-87.90284&adults=2&startDate=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=RESIDENCE)

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Save an average of 15% on thousands of hotels when you're signed in

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## Top Hillside Hotel Reviews

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

### Aloft Chicago Mag Mile

10/10 Excellent

"good environment all around "

[](https://expedia.com/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.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

"Great location, close to everything, clean room, friendly staff, included breakfast a plus. Thank you. "

[](https://expedia.com/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.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

"Tudo impecável "

[](https://expedia.com/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.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

"My new Favorite Property in Chicago…loved It💙"

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

![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg)

### Hilton Chicago/Magnificent Mile Suites

10/10 Excellent

"Genial ubicación "

[](https://expedia.com/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information)

![The Royal Sonesta Chicago Downtown](https://images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg)

### The Royal Sonesta Chicago Downtown

10/10 Excellent

"Excellent room with amazing views. Really friendly and helpful staff. Josh at reception was extremely good to us! Excellent location centre of everything. Would definitely recommend this hotel "

[](https://expedia.com/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information)

![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg)

### Congress Plaza Hotel

10/10 Excellent

"Staff was great. Clean rooms ,great location "

[](https://expedia.com/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information)

![River Hotel](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5_y.jpg)

### River Hotel

10/10 Excellent

"Amazing place!"

[](https://expedia.com/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information)

![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg)

### theWit Chicago, a Hilton Hotel

10/10 Excellent

"Awesome stay. I love the Witt."

[](https://expedia.com/Chicago-Hotels-TheWit-Chicago-A-DoubleTree-By-Hilton-Hotel.h2463437.Hotel-Information)

## Find out more about Hillside

**Everything you need to know about Hillside vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Hillside vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Hillside vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Hillside vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Hillside. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Hillside in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $106 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Hillside rentals**

At Expedia, we put the best Hillside vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Hillside rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Hillside vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Hillside. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

- Trending destinations on Expedia.com
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- [Clearwater Beach Vacation Rentals ](https://www.expedia.com/Clearwater-Beach-Vacation-Rentals.d10759.Travel-Guide-VacationRentals)
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- [Florida Keys Vacation Rentals ](https://www.expedia.com/Florida-Keys-Vacation-Rentals.d6023765.Travel-Guide-VacationRentals)
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- [Lake of the Ozarks Vacation Rentals ](https://www.expedia.com/Lake-Ozark-Vacation-Rentals.d177772.Travel-Guide-VacationRentals)
- [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [Apartments in Hillside ](https://expedia.com/Hillside-Apartments.d8353-aaApartments.Travel-Guide-Accommodation)
- [Vacation Homes in Hillside ](https://expedia.com/Hillside-Private-Vacation-Homes.d8353-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Condo Rentals in Hillside ](https://expedia.com/Hillside-Condos.d8353-aaCondos.Travel-Guide-Accommodation)
- [Aparthotels in Hillside ](https://expedia.com/Hillside-Apart-Hotels.d8353-aaApartHotels.Travel-Guide-Accommodation)
- [Motels in Hillside ](https://expedia.com/Hillside-Motels.d8353-aaMotels.Travel-Guide-Accommodation)
- [Cottages in Hillside ](https://expedia.com/Hillside-Cottages.d8353-aaCottages.Travel-Guide-Accommodation)
- [B&B in Hillside ](https://expedia.com/Hillside-Bed-And-Breakfast.d8353-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Guest Houses in Hillside ](https://expedia.com/Hillside-Guest-Houses.d8353-aaGuestHouses.Travel-Guide-Accommodation)
- [Hostels in Hillside ](https://expedia.com/Hillside-Hostels.d8353-aaHostels.Travel-Guide-Accommodation)
- [Villas in Hillside ](https://expedia.com/Hillside-Villas.d8353-aaVillas.Travel-Guide-Accommodation)
- [Resorts in Hillside ](https://expedia.com/Hillside-Resorts.d8353-aaResorts.Travel-Guide-Accommodation)
- [Houseboats in Hillside ](https://expedia.com/Hillside-Houseboats.d8353-aaHouseboats.Travel-Guide-Accommodation)
- [Residences in Hillside ](https://expedia.com/Hillside-Residences.d8353-aaResidences.Travel-Guide-Accommodation)
- [Farmstay in Hillside ](https://expedia.com/Hillside-Agritourism.d8353-aaAgritourism.Travel-Guide-Accommodation)
- [Cabin Rentals in Hillside ](https://expedia.com/Hillside-Cabins.d8353-aaCabins.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find a vacation rental in Hillside?

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

### What can I see and do in Hillside?

### What are vacation rentals like in Hillside?

### Expedia's Latest Trends

Hotels

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- [Schaumburg Hotels](https://expedia.com/Schaumburg-Hotels.d8107.Travel-Guide-Hotels)
- [Arlington Heights Hotels](https://expedia.com/Arlington-Heights-Hotels.d6231.Travel-Guide-Hotels)
- [Des Plaines Hotels](https://expedia.com/Des-Plaines-Hotels.d7863.Travel-Guide-Hotels)
- [Waukegan Hotels](https://expedia.com/Waukegan-Hotels.d10174.Travel-Guide-Hotels)
- [Hoffman Estates Hotels](https://expedia.com/Hoffman-Estates-Hotels.d7602.Travel-Guide-Hotels)
- [Rosemont Hotels](https://expedia.com/Rosemont-Hotels.d7581.Travel-Guide-Hotels)
- [Oak Brook Hotels](https://expedia.com/Oak-Brook-Hotels.d9218.Travel-Guide-Hotels)
- [Glenview Hotels](https://expedia.com/Glenview-Hotels.d8006.Travel-Guide-Hotels)
- [Oak Lawn Hotels](https://expedia.com/Oak-Lawn-Hotels.d9227.Travel-Guide-Hotels)
- [Evanston Hotels](https://expedia.com/Evanston-Hotels.d8049.Travel-Guide-Hotels)
- [Naperville Hotels](https://expedia.com/Naperville-Hotels.d9009.Travel-Guide-Hotels)
- [Wheaton Hotels](https://expedia.com/Wheaton-Hotels.d7599.Travel-Guide-Hotels)
- [Bolingbrook Hotels](https://expedia.com/Bolingbrook-Hotels.d55064.Travel-Guide-Hotels)
- [Elmhurst Hotels](https://expedia.com/Elmhurst-Hotels.d7836.Travel-Guide-Hotels)
- [Orland Park Hotels](https://expedia.com/Orland-Park-Hotels.d9270.Travel-Guide-Hotels)
- [Oak Park Hotels](https://expedia.com/Oak-Park-Hotels.d9228.Travel-Guide-Hotels)

Cars

- [Car rentals in Naperville](https://expedia.com/Car-Rentals-In-Naperville.d9009.Car-Rental-Guide)
- [Car rentals in Des Plaines](https://expedia.com/Car-Rentals-In-Des-Plaines.d7863.Car-Rental-Guide)
- [Car rentals in Schaumburg](https://expedia.com/Car-Rentals-In-Schaumburg.d8107.Car-Rental-Guide)
- [Car rentals in Bolingbrook](https://expedia.com/Car-Rentals-In-Bolingbrook.d55064.Car-Rental-Guide)
- [Car rentals in Orland Park](https://expedia.com/Car-Rentals-In-Orland-Park.d9270.Car-Rental-Guide)

Activities

- [Things to do in Schaumburg](https://expedia.com/Things-To-Do-In-Schaumburg.d8107.Travel-Guide-Activities)

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