Title: Westchester Vacation Rentals from CA $151: Short-Term Rentals for 2026 | Expedia.ca

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## Check prices for these dates

In two weeks

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=7758&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 two months

[May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=7758&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 12 - Jun 14](https://www.expedia.ca/Hotel-Search?regionId=7758&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 10 - Jul 12](https://www.expedia.ca/Hotel-Search?regionId=7758&startDate=2026-07-10&endDate=2026-07-12&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

![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)

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

![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/96000000/95140000/95134600/95134539/w905h683x59y0-8cb3eda8.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.ca/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.

CA $203

CA $556 total

includes taxes & fees

Mar 17 - Mar 18

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

![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)

![3 bedrooms, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/114000000/113430000/113424300/113424225/8950b29d.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)

### 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)

"Great location, price and the place was well kept and accommodating."

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

Carl M.

CA $306

CA $699 total

includes taxes & fees

Mar 17 - Mar 18

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

![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/e4c99836.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/125000000/124260000/124258400/124258393/8cccb6c6.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 $429

CA $939 total

includes taxes & fees

Apr 7 - Apr 8

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99350000/99343900/99343866/w1200h799x0y1-c9026eae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99350000/99343900/99343866/w1199h799x1y1-4f4c0bde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99350000/99343900/99343866/69b0df95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/100000000/99350000/99343900/99343866/w1200h799x0y1-7d6c256b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern 3BR Home w/ Huge Backyard | LCP Collection

[](https://www.expedia.ca/Chicago-Hotels-Modern-3BR-Home-W-Huge-Backyard-LCP-Collection.h99343866.Hotel-Information)

Westchester

10/10

Exceptional

(1 review)

"Everything was exactly like we hoped and ghen sum. Great single level floor plan with garage access."

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

Alva E.

[](https://www.expedia.ca/Chicago-Hotels-Modern-3BR-Home-W-Huge-Backyard-LCP-Collection.h99343866.Hotel-Information)

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/127000000/126870000/126868600/126868501/63b2031b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/127000000/126870000/126868600/126868501/4340a3f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/127000000/126870000/126868600/126868501/a86d78a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/127000000/126870000/126868600/126868501/3635d1b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### LIVN Millennium Park Downtown Chicago Studio

[](https://www.expedia.ca/Chicago-Hotels-LIVN-Millennium-Park-Downtown-Chicago-Studio.h126868501.Hotel-Information)

Downtown Chicago

CA $167

CA $230 total

includes taxes & fees

Apr 6 - Apr 7

[](https://www.expedia.ca/Chicago-Hotels-LIVN-Millennium-Park-Downtown-Chicago-Studio.h126868501.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/127000000/126870000/126868600/126868509/df58fd48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/127000000/126870000/126868600/126868509/7cc24bd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/127000000/126870000/126868600/126868509/1ec4b697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/127000000/126870000/126868600/126868509/f5af72ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### LIVN Millennium Park Downtown Chicago 1 BR

[](https://www.expedia.ca/Chicago-Hotels-LIVN-Millennium-Park-Downtown-Chicago-1-BR.h126868509.Hotel-Information)

Downtown Chicago

CA $200

CA $269 total

includes taxes & fees

Apr 6 - Apr 7

[](https://www.expedia.ca/Chicago-Hotels-LIVN-Millennium-Park-Downtown-Chicago-1-BR.h126868509.Hotel-Information)

![Point of interest](https://images.trvl-media.com/lodging/127000000/126870000/126868500/126868474/4fe2a406.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bathroom](https://images.trvl-media.com/lodging/127000000/126870000/126868500/126868474/3071f4cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/127000000/126870000/126868500/126868474/17b67d11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room](https://images.trvl-media.com/lodging/127000000/126870000/126868500/126868474/62ffbce8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### LIVN West Loop Chicago 1 BR

[](https://www.expedia.ca/Chicago-Hotels-LIVN-West-Loop-Chicago-1-BR.h126868474.Hotel-Information)

Downtown Chicago

CA $274

CA $359 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Chicago-Hotels-LIVN-West-Loop-Chicago-1-BR.h126868474.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)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/8ec83200.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)

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

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

CA $121

CA $273 total

includes taxes & fees

Mar 17 - Mar 18

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

![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)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/a5975d89.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 $121

CA $273 total

includes taxes & fees

Mar 19 - Mar 20

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

![Lobby](https://images.trvl-media.com/lodging/118000000/117520000/117515200/117515137/6c271db9.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/118000000/117520000/117515200/117515137/7004f6ad.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 $268

CA $701 total

includes taxes & fees

Mar 18 - Mar 19

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

![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)

![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

(8 reviews)

"Great communication and hosts. Location and unit was perfect."

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

Greg C.

CA $121

CA $273 total

includes taxes & fees

Mar 19 - Mar 20

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

![Garden](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/ccaab668.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

(1,106 reviews)

"The kitchen was great and check-in was easy."

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

Marshal

CA $162

CA $231 total

includes taxes & fees

Mar 19 - Mar 20

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

![Interior](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/df8744f2.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)

### 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)

"We had a wonderful stay at this Vrbo! The home was spotless, cozy, and exactly as described. The host was friendly, responsive, and made everything easy from check-in to check-out. We would absolutely stay here again. Highly recommend!"

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

Brianna K.

CA $155

CA $306 total

includes taxes & fees

Mar 24 - Mar 25

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

![TV, offices](https://images.trvl-media.com/lodging/123000000/122190000/122181300/122181232/e8f7392e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122190000/122181300/122181232/cf7a7d36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/123000000/122190000/122181300/122181232/7906acf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/123000000/122190000/122181300/122181232/32a236ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern West Loop Gem-City Views & Prime Location 6

[](https://www.expedia.ca/Chicago-Hotels-Modern-West-Loop-Gem-City-Views-Prime-Location-6.h122181232.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(15 reviews)

"Great place"

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

Daniel L.

CA $280

CA $879 total

includes taxes & fees

Mar 29 - Mar 30

[](https://www.expedia.ca/Chicago-Hotels-Modern-West-Loop-Gem-City-Views-Prime-Location-6.h122181232.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)

![TV](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/96789a75.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)

### 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

8.0/10

Very good

(2 reviews)

"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 $121

CA $273 total

includes taxes & fees

Mar 17 - Mar 18

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

![Interior](https://images.trvl-media.com/lodging/119000000/118410000/118409500/118409489/44e9262b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, offices](https://images.trvl-media.com/lodging/119000000/118410000/118409500/118409489/7fa2461a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118410000/118409500/118409489/ccec1f1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, offices](https://images.trvl-media.com/lodging/119000000/118410000/118409500/118409489/715d39bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Premium Urban 4BR - Perfect Mix of Comfort & Location

[](https://www.expedia.ca/Chicago-Hotels-High-Rise-4BR-W-Views.h118409489.Hotel-Information)

Near North Side

10/10

Exceptional

(1 review)

"Nice place, clean property, great views "

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

Zach L.

CA $959

CA $1,698 total

includes taxes & fees

Mar 25 - Mar 26

[](https://www.expedia.ca/Chicago-Hotels-High-Rise-4BR-W-Views.h118409489.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)

![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)

![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)

![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

(443 reviews)

"Great value, friendly staff"

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

Marcus

CA $188

CA $254 total

includes taxes & fees

Apr 5 - Apr 6

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

![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)

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

9.4/10

Exceptional

(186 reviews)

"Nice area if you are renting a car, be aware that you would have to pay for street parking or go over a few blocks and park in a parking lot."

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

Daysha

CA $190

CA $336 total

includes taxes & fees

Apr 12 - Apr 13

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

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792828/81360f2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792828/9a4a0623.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792828/dd022100.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792828/d6084ece.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy & Furnished 2BR Unit

[](https://www.expedia.ca/Chicago-Hotels-Cozy-Furnished-2BR-Unit.h116792828.Hotel-Information)

Lincoln Square

9.2/10

Wonderful

(17 reviews)

"Very cozy, amenities in great condition."

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

Kaitlin T.

CA $110

CA $286 total

includes taxes & fees

Mar 24 - Mar 25

[](https://www.expedia.ca/Chicago-Hotels-Cozy-Furnished-2BR-Unit.h116792828.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792691/1897ede8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792691/83c9368f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792691/68407ff1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792691/fca43c92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish and Roomy 2BR in Chicago

[](https://www.expedia.ca/Chicago-Hotels-Stylish-And-Roomy-2BR-In-Chicago.h116792691.Hotel-Information)

Edgewater

9.0/10

Wonderful

(14 reviews)

"Clean room, easy, check-in, great location"

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

brent w.

CA $110

CA $286 total

includes taxes & fees

Mar 25 - Mar 26

[](https://www.expedia.ca/Chicago-Hotels-Stylish-And-Roomy-2BR-In-Chicago.h116792691.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=2026-03-30&endDate=2026-03-31&regionId=7758&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=Westchester%2C+Illinois%2C+United+States+of+America&regionId=7758&latLong=41.849834%2C-87.880676&adults=2&startDate=2026-06-14&d1=2026-06-14&endDate=2026-06-17&d2=2026-06-17&lodging=APART_HOTEL)

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=2026-06-14&d1=2026-06-14&endDate=2026-06-17&d2=2026-06-17&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=2026-06-14&d1=2026-06-14&endDate=2026-06-17&d2=2026-06-17&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=2026-06-14&d1=2026-06-14&endDate=2026-06-17&d2=2026-06-17&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=2026-06-14&d1=2026-06-14&endDate=2026-06-17&d2=2026-06-17&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=2026-06-14&d1=2026-06-14&endDate=2026-06-17&d2=2026-06-17&lodging=COTTAGE)

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## Top Westchester Hotel Reviews

![The Wade](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/109a2156_y.jpg)

### The Wade

8/10 Good

"Room was clean, staff was very helpful although there was only one bartender on St Pattys weekend. Valet were very nice and helpful. Great views of the lake and safe neighborhood. Would stay again. "

[](https://expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information)

![Fairmont Chicago at Millennium Park](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/8bd99f5f_y.jpg)

### Fairmont Chicago at Millennium Park

2/10 Terrible

"Rooms are outdated compared to the lobby "

[](https://expedia.ca/Chicago-Hotels-Fairmont-Chicago-At-Millennium-Park.h15937.Hotel-Information)

![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2_y.jpg)

### Congress Plaza Hotel

6/10 Okay

"Hot water pressure was very very low. Had to leave the shower running for an hour turn it off completely then turn it back on for the pressure to work. "

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

![Aloft Chicago Mag Mile](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/58ac280a_y.jpg)

### Aloft Chicago Mag Mile

10/10 Excellent

"Yes"

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

![Swissotel - Chicago](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/3cb3732b_y.jpg)

### Swissotel - Chicago

10/10 Excellent

"If you visit on St. Patrick's Day weekend you have a perfect view of the Chicago River being dyed from the hotel if you get a "river view" room. You are directly across the street if you want to watch the river being dyed from the riverwalk. You are about 4 blocks from viewing the parade."

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

"Staff was amazing, we were sad to go was fancier than I was used to. So many items required room key to function but i caught on and not feeling judged by not being sure what to do was appreciated. "

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

![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/24d28405_y.jpg)

### Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent

"Clean room"

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

![The Royal Sonesta Chicago Downtown](https://images.trvl-media.com/lodging/1000000/20000/17600/17543/fa2dd97c_y.jpg)

### The Royal Sonesta Chicago Downtown

8/10 Good

"The staff in the restaurant on Friday night did not look anyone in the eye and actually avoided eye contact. It was not extremely busy especially for the weekend that was ahead, but the service was extremly slow, not good nor was the bar staff friendly in that area. "

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

![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/a215cd17_y.jpg)

### Hilton Chicago/Magnificent Mile Suites

10/10 Excellent

"Wonder place to stay. Staff was amazing. Room was spotless!! On site restaurant was great. Within walking distance of events. "

[](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.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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- [Prince Edward Island Vacation Rentals ](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations)
- [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?

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

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

Packages

- [Golf Trip](https://expedia.ca/Golf.d6132095.Destination-Travel-Guides)

General

- [Visit Evanston](https://expedia.ca/Evanston.dx8049)
- [Visit Melrose Park](https://expedia.ca/Melrose-Park.dx8800)
- [Visit Vernon Hills](https://expedia.ca/Vernon-Hills.dx6371)
- [Visit Dolton](https://expedia.ca/Dolton.dx6132086)
- [Visit Schaumburg](https://expedia.ca/Schaumburg.dx8107)
- [Visit Elk Grove Village](https://expedia.ca/Elk-Grove-Village.dx7833)
- [Visit Hoffman Estates](https://expedia.ca/Hoffman-Estates.dx7602)
- [Visit Rosemont](https://expedia.ca/Rosemont.dx7581)

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