Title: Westchester Vacation Rentals from CA $220: Short-Term Rentals for 2026 | Expedia.ca

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# Westchester Vacation Rentals

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## Check prices for these dates

Tonight

[Jan 12 - Jan 13](https://www.expedia.ca/Hotel-Search?regionId=7758&startDate=2026-01-12&endDate=2026-01-13&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Jan 13 - Jan 14](https://www.expedia.ca/Hotel-Search?regionId=7758&startDate=2026-01-13&endDate=2026-01-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=7758&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=7758&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Westchester vacation rentals

![TV, offices](https://images.trvl-media.com/lodging/125000000/124260000/124258400/124258393/c8b2a106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124260000/124258400/124258393/e9783232.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124260000/124258400/124258393/e4c99836.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/125000000/124260000/124258400/124258393/00b13eb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Westchester Retreat Near Chicago & Parks

[](https://www.expedia.ca/Chicago-Hotels-Cozy-Westchester-Retreat-Near-Chicago-Parks.h124258393.Hotel-Information)

Westchester

CA $399

CA $888 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Chicago-Hotels-Cozy-Westchester-Retreat-Near-Chicago-Parks.h124258393.Hotel-Information)

![Fireplace](https://images.trvl-media.com/lodging/114000000/113430000/113424300/113424225/35b3a204_edited_bda3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113430000/113424300/113424225/6a755c90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113430000/113424300/113424225/w1200h798x0y5-177b5483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113430000/113424300/113424225/w1196h795x0y0-ec19116b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### King Bed, Game Room & Fire Pit | LCP Collection

[](https://www.expedia.ca/Chicago-Hotels-King-Bed.h113424225.Hotel-Information)

Westchester

8.0/10

Very good

(2 reviews)

"The house itself was beautiful! The yard was perfect for relaxing, and the home was spacious, comfortable, and very clean.Unfortunately, we did run into a few issues during our stay. The king bed in the master bedroom was broken and could not be used. A maintenance person showed up after hours without any prior notice or communication from the host, which made us uncomfortable letting them in. We decided to forgo use of the main bedroom rather than allow an unannounced visitor. In addition,...

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

Trey G.

CA $310

CA $704 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Chicago-Hotels-King-Bed.h113424225.Hotel-Information)

![View from property](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/9649f522.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Business Apartment, City View | Living area](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/a356a2da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/ecebb166.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![75-inch Smart TV with digital channels, Netflix, streaming services](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/87d09298.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### ENVITAE Hotel 4 Bedroom Luxury Apartments

[](https://www.expedia.ca/Chicago-Hotels-4BR-Corporate-Suite-Central-And-Modern.h118632066.Hotel-Information)

Near North Side

9.4/10

Exceptional

(10 reviews)

"Good for family, enjoyed the stay"

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

Karthik

CA $1,980

CA $2,616 total

includes taxes & fees

Jan 16 - Jan 17

[](https://www.expedia.ca/Chicago-Hotels-4BR-Corporate-Suite-Central-And-Modern.h118632066.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103920000/103911700/103911623/c1fee4a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/104000000/103920000/103911700/103911623/3e52d1da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103920000/103911700/103911623/499614fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103920000/103911700/103911623/0fe3d073.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Less is more! Pet friendly Tiny Home near Chicago! 

[](https://www.expedia.ca/Chicago-Hotels-Less-Is-More-Pet-Friendly-Tiny-Home-Near-Chicago.h103911623.Hotel-Information)

Burr Ridge

9.8/10

Exceptional

(37 reviews)

"We loved it! We were in for a short time and it was perfect!!"

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

nicole l.

CA $144

CA $292 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Chicago-Hotels-Less-Is-More-Pet-Friendly-Tiny-Home-Near-Chicago.h103911623.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)

![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, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/2a6e88ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Apartment, 2 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/83f39cf6.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

(1,041 reviews)

"Place was very nice and clean. We enjoyed the stay there. Will book it again when we come back to Chicago visit again. "

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

Khalid

CA $153

CA $220 total

includes taxes & fees

Jan 13 - Jan 14

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

![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.ca/Chicago-Hotels-LEVEL-Furnished-Living-Chicago.h39805843.Hotel-Information)

Downtown Chicago

9.0/10

Wonderful

(411 reviews)

"Great location, clean room and friendly staff!"

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

Scott

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

![TV, offices](https://images.trvl-media.com/lodging/125000000/124200000/124198600/124198522/385925ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124200000/124198600/124198522/74a8f435.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124200000/124198600/124198522/13f4699d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/125000000/124200000/124198600/124198522/cce101c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chicago-Themed 1BR in a Central Spot near Downtown

[](https://www.expedia.ca/Chicago-Hotels-Chicago-Themed-1BR-In-A-Central-Spot-Near-Downtown.h124198522.Hotel-Information)

Downtown Chicago

CA $88

CA $234 total

includes taxes & fees

Jan 14 - Jan 15

[](https://www.expedia.ca/Chicago-Hotels-Chicago-Themed-1BR-In-A-Central-Spot-Near-Downtown.h124198522.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)

![Desk, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/c18afdca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/6446ea65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/29c0e5ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

CA $96

CA $230 total

includes taxes & fees

Jan 13 - Jan 14

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

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793104/e4126779.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/117000000/116800000/116793200/116793104/53fb8853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793104/992e40df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793104/052710d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Chicago-Hotels-Twice-As-Nice-Chic-2BR-Stay-With-Style-Space.h116793104.Hotel-Information)

Downtown Chicago

9.6/10

Exceptional

(20 reviews)

"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "

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

Shederia P.

CA $96

CA $265 total

includes taxes & fees

Jan 14 - Jan 15

[](https://www.expedia.ca/Chicago-Hotels-Twice-As-Nice-Chic-2BR-Stay-With-Style-Space.h116793104.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)

![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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/2e28ea21.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.ca/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

CA $88

CA $234 total

includes taxes & fees

Jan 15 - Jan 16

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

![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)

![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)

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

### Sun-Drenched 1BR Apartment

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

CA $88

CA $234 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/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)

![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)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/e3efb27d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Downtown Chicago

9.8/10

Exceptional

(11 reviews)

"Great host comfortable bed close to restaurants and parks"

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

Alana C.

CA $88

CA $234 total

includes taxes & fees

Jan 15 - Jan 16

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

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/b56ca762.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)

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

### West Loop Living – Bright 1BR

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

Downtown Chicago

10/10

Exceptional

(6 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

CA $88

CA $234 total

includes taxes & fees

Jan 22 - Jan 23

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

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/b23ea222.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/d38a815b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/f0dc9495.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/3ed1c84b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The One: A 1BR Stay That Feels Like Home

[](https://www.expedia.ca/Chicago-Hotels-All-Set-Up-Furnished-1BR-Unit.h116793110.Hotel-Information)

Downtown Chicago

8.4/10

Very good

(5 reviews)

"Very nice condo in a quiet neighborhood"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Patrick

CA $88

CA $234 total

includes taxes & fees

Jan 15 - Jan 16

[](https://www.expedia.ca/Chicago-Hotels-All-Set-Up-Furnished-1BR-Unit.h116793110.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)

![Business centre](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/825d44e9.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

CA $173

CA $334 total

includes taxes & fees

Jan 22 - Jan 23

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

![Interior](https://images.trvl-media.com/lodging/118000000/117520000/117515200/117515137/d8e9b0e1.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)

![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)

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

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

CA $139

CA $435 total

includes taxes & fees

Jan 13 - Jan 14

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

![Interior](https://images.trvl-media.com/lodging/125000000/124200000/124198600/124198521/258f7b35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/125000000/124200000/124198600/124198521/4ab094fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/125000000/124200000/124198600/124198521/be5c4a31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124200000/124198600/124198521/223628d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish Japanese-Themed 2BR Apt Close to Downtown

[](https://www.expedia.ca/Chicago-Hotels-Stylish-Japanese-Themed-2BR-Apt-Close-To-Downtown.h124198521.Hotel-Information)

Downtown Chicago

CA $96

CA $265 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Chicago-Hotels-Stylish-Japanese-Themed-2BR-Apt-Close-To-Downtown.h124198521.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)

![Property grounds](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/4ffd1328.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 Apt w/ Laundry

[](https://www.expedia.ca/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 traveller

CA $88

CA $234 total

includes taxes & fees

Jan 21 - Jan 22

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

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792754/1310976f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792754/2bfb9517.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/117000000/116800000/116792800/116792754/a190b9fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792754/716fc9f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Complete 1BR Home Sum

[](https://www.expedia.ca/Chicago-Hotels-1BR-Chic-Equipped-Apt.h116792754.Hotel-Information)

Downtown Chicago

CA $88

CA $234 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Chicago-Hotels-1BR-Chic-Equipped-Apt.h116792754.Hotel-Information)

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793083/e1aa934f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793083/e682556b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793083/829bcf7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793083/d10b773f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Studio Near UChicago

[](https://www.expedia.ca/Chicago-Hotels-Modern-Studio-Near-UChicago.h116793083.Hotel-Information)

Hyde Park

9.4/10

Exceptional

(12 reviews)

"Clean room and convenient location! "

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

Gabriela

CA $79

CA $211 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Chicago-Hotels-Modern-Studio-Near-UChicago.h116793083.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.

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## Find vacation rentals that suit your style

Aparthotels

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Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Westchester%2C+Illinois%2C+United+States+of+America&regionId=7758&latLong=41.849834%2C-87.880676&adults=2&startDate=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&lodging=APARTMENT)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Westchester%2C+Illinois%2C+United+States+of+America&regionId=7758&latLong=41.849834%2C-87.880676&adults=2&startDate=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&lodging=VACATION_HOME)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Westchester%2C+Illinois%2C+United+States+of+America&regionId=7758&latLong=41.849834%2C-87.880676&adults=2&startDate=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&lodging=CONDO)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Westchester%2C+Illinois%2C+United+States+of+America&regionId=7758&latLong=41.849834%2C-87.880676&adults=2&startDate=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&lodging=VILLA)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Westchester%2C+Illinois%2C+United+States+of+America&regionId=7758&latLong=41.849834%2C-87.880676&adults=2&startDate=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&lodging=COTTAGE)

Residences

[](https://www.expedia.ca/Hotel-Search?destination=Westchester%2C+Illinois%2C+United+States+of+America&regionId=7758&latLong=41.849834%2C-87.880676&adults=2&startDate=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&lodging=RESIDENCE)

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## Top Westchester Hotel Reviews

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

### Eurostars Magnificent Mile

10/10 Excellent

"Amazing"

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

![Swissotel - Chicago](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/7af111e2_y.jpg)

### Swissotel - Chicago

10/10 Excellent

"Hotel staff was very friendly and helpful. Beautiful vi"

[](https://expedia.ca/Chicago-Hotels-Swissotel-Chicago.h17288.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

"The room was perfect will definitely book another stay here "

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

![The Whitehall Hotel, BW Premier Collection](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e_y.jpg)

### The Whitehall Hotel, BW Premier Collection

10/10 Excellent

"Yes. It was clean and beautiful! Nice area "

[](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.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

"Great staff and very clean. "

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

"The room was luxurious and the staff was extremely friendly and helpful!"

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

![Silversmith Hotel Chicago Downtown](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/da03d6b4_y.jpg)

### Silversmith Hotel Chicago Downtown

10/10 Excellent

"Fantastic location for the el. Rooms Are somewhat dated with paint and carpet, but we weren’t there to spend time in the room. So I don’t fault them for any of that. Some of the carpet is coming up from floors which is a trip hazard and should be addressed but again- not something that’s affecting their rating. The bed was very comfortable, good WiFi; excellent bathroom water pressure and very hot water which is nice. Close to the CSO, all access for the CTA and great restaurants near by. I do not recommend eating at the restaurant on site- you can be anywhere in the city in 20 minutes from the el platform so I highly Recommend staying here if you’re open to walking and exploring "

[](https://expedia.ca/Chicago-Hotels-Silversmith-Hotel-Chicago-Downtown.h116674.Hotel-Information)

![Club Quarters Hotel Wacker at Michigan, Chicago](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/f3eb640d_y.jpg)

### Club Quarters Hotel Wacker at Michigan, Chicago

10/10 Excellent

"Super fast and easy check in / out experience, amazing location and very affordable "

[](https://expedia.ca/Chicago-Hotels-Club-Quarters-Hotel.h889753.Hotel-Information)

![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

"Great hotel "

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

## Find out more about Westchester

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 Westchester. 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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- [Penticton Vacation Rentals ](https://www.expedia.ca/Penticton-Vacation-Rentals.d4135.Travel-Guide-VacationRentals)
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- [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

- [Apartments in Westchester ](https://expedia.ca/Westchester-Apartments.d7758-aaApartments.Travel-Guide-Accommodation)
- [Vacation Homes in Westchester ](https://expedia.ca/Westchester-Private-Vacation-Homes.d7758-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Condo Rentals in Westchester ](https://expedia.ca/Westchester-Condos.d7758-aaCondos.Travel-Guide-Accommodation)
- [Aparthotels in Westchester ](https://expedia.ca/Westchester-Apart-Hotels.d7758-aaApartHotels.Travel-Guide-Accommodation)
- [Motels in Westchester ](https://expedia.ca/Westchester-Motels.d7758-aaMotels.Travel-Guide-Accommodation)
- [Cottages in Westchester ](https://expedia.ca/Westchester-Cottages.d7758-aaCottages.Travel-Guide-Accommodation)
- [B&B in Westchester ](https://expedia.ca/Westchester-Bed-And-Breakfast.d7758-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Guest Houses in Westchester ](https://expedia.ca/Westchester-Guest-Houses.d7758-aaGuestHouses.Travel-Guide-Accommodation)
- [Hostels in Westchester ](https://expedia.ca/Westchester-Hostels.d7758-aaHostels.Travel-Guide-Accommodation)
- [Villas in Westchester ](https://expedia.ca/Westchester-Villas.d7758-aaVillas.Travel-Guide-Accommodation)
- [Resorts in Westchester ](https://expedia.ca/Westchester-Resort-Hotels.d7758-aaResortHotels.Travel-Guide-Accommodation)
- [Houseboats in Westchester ](https://expedia.ca/Westchester-Houseboats.d7758-aaHouseboats.Travel-Guide-Accommodation)
- [Residences in Westchester ](https://expedia.ca/Westchester-Residences.d7758-aaResidences.Travel-Guide-Accommodation)
- [Farmstay in Westchester ](https://expedia.ca/Westchester-Agritourism.d7758-aaAgritourism.Travel-Guide-Accommodation)
- [Cabin Rentals in Westchester ](https://expedia.ca/Westchester-Cabins.d7758-aaCabins.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find vacation rentals in Westchester?

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

### How many vacation rentals are there in Westchester?

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

### What are vacation rentals like in Westchester?

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Flights

- [Flights from Toronto to Dubai](https://expedia.ca/lp/flights/yyz/dxb/toronto-to-dubai)
- [Flights to Dollar](https://expedia.ca/Cheap-Flights-To-Dollar.d6193375.Travel-Guide-Flights)
- [Flights to Rosemont](https://expedia.ca/Cheap-Flights-To-Rosemont.d7581.Travel-Guide-Flights)

Activities

- [Things to do in Des Plaines](https://expedia.ca/Things-To-Do-In-Des-Plaines.d7863.Travel-Guide-Activities)
- [Things to do in New York](https://expedia.ca/Things-To-Do-In-New-York.d178293.Travel-Guide-Activities)

Packages

- [Navy Pier](https://expedia.ca/Navy-Pier-Downtown-Chicago.d6069215.Vacation-Attraction)
- [Lincoln Park Zoo](https://expedia.ca/Lincoln-Park-Zoo-Lincoln-Park.d6065147.Vacation-Attraction)
- [Willis Tower](https://expedia.ca/Willis-Tower-Downtown-Chicago.d6064069.Vacation-Attraction)
- [Griffin Museum of Science and Industry](https://expedia.ca/Griffin-Museum-Of-Science-And-Industry-Hyde-Park.d6064043.Vacation-Attraction)
- [Golf Trip](https://expedia.ca/Golf.d6132095.Destination-Travel-Guides)
- [Grant Park](https://expedia.ca/Grant-Park-Downtown-Chicago.d507389.Vacation-Attraction)

General

- [Visit Evanston](https://expedia.ca/Evanston.dx8049)
- [Visit Schaumburg](https://expedia.ca/Schaumburg.dx8107)
- [Visit Elk Grove Village](https://expedia.ca/Elk-Grove-Village.dx7833)

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