Title: Winnetka Apartment Rentals from CA $228 | Expedia.ca

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# Search Apartment Rentals in Winnetka

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## Check prices for these dates

Next weekend

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=175751&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=175751&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=175751&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)

In two months

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=175751&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Winnetka apartments

![Interior](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/1309495b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/0412ba3d.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/eab5965a.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/c64cc369.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Downtown Chicago

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

10/10

Exceptional

(5)

"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 $95

CA $228 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](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)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793104/61009377.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/117000000/116800000/116793200/116793104/1ab3553c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793104/964f82ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Downtown Chicago

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

9.6/10

Exceptional

(14)

"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 $109

CA $278 total

includes taxes & fees

Dec 18 - Dec 19

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/c52efc06.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)

![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)

![Shower, hair dryer](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/664fb229.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Downtown Chicago

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

10/10

Exceptional

(4)

"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 $87

CA $232 total

includes taxes & fees

Jan 6 - Jan 7, 2026

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

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/adbf623a.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)

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

### Apartment in Downtown Chicago

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

10/10

Exceptional

(1)

"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 $87

CA $232 total

includes taxes & fees

Jan 6 - Jan 7, 2026

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

![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)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/93c17f93.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/117000000/116800000/116793000/116792936/003c4277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/c3fddccc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Downtown Chicago

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

10/10

Exceptional

(2)

"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "

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

Tyler B.

CA $87

CA $232 total

includes taxes & fees

Jan 6 - Jan 7, 2026

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/3cc0a9a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/9b704ea8.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/117000000/116800000/116793100/116793043/8c87c7e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/89a0d93e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Downtown Chicago

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

10/10

Exceptional

(10)

"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"

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

Jacob D.

CA $87

CA $232 total

includes taxes & fees

Jan 5 - Jan 6, 2026

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

![TV, offices](https://images.trvl-media.com/lodging/123000000/122190000/122181300/122181208/ccf3567c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122190000/122181300/122181208/w1176h801x0y0-ddea31cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Spa](https://images.trvl-media.com/lodging/123000000/122190000/122181300/122181208/442d7579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/123000000/122190000/122181300/122181208/0a11e27d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Downtown Chicago

[](https://www.expedia.ca/Chicago-Hotels-Modern-West-Loop-Gem-City-Views-Prime-Location-4.h122181208.Hotel-Information)

10/10

Exceptional

(2)

"Amazing accommodation"

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

Jiri N.

CA $182

CA $501 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Chicago-Hotels-Modern-West-Loop-Gem-City-Views-Prime-Location-4.h122181208.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/50bbce16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/31d1cbc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/fd6dad17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/3815ff36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Downtown Chicago

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

8.4/10

Very good

(5)

"Very nice condo in a quiet neighborhood"

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

Patrick

CA $87

CA $232 total

includes taxes & fees

Jan 1 - Jan 2, 2026

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

![TV, offices](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712513/f6b82937.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712513/fbe3d983.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712513/80c93096.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712513/13a40e63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Downtown Chicago

[](https://www.expedia.ca/Chicago-Hotels-South-Loop-Rooftop-With-In-Out-Parking.h117712513.Hotel-Information)

9.0/10

Wonderful

(2)

"We loved the property! It was well kept, clean, with a seamless check in and check out process! I wish the parking garage would have been closer but otherwise everything was great! Shout out to the host for his promptness with all my questions! I would recommend this place if they are looking for a place to stay! "

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

Bridney K.

CA $143

CA $439 total

includes taxes & fees

Jan 8 - Jan 9, 2026

[](https://www.expedia.ca/Chicago-Hotels-South-Loop-Rooftop-With-In-Out-Parking.h117712513.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712527/2d716375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712527/c67cddf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712527/b6735e4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712527/4b557c1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Downtown Chicago

[](https://www.expedia.ca/Chicago-Hotels-River-North-Rooftop-With-In-Out-Parking-1.h117712527.Hotel-Information)

9.0/10

Wonderful

(2)

"Awesome location, great place would definitely recommend will hopefully return"

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

lucas c.

CA $196

CA $511 total

includes taxes & fees

Dec 27 - Dec 28

[](https://www.expedia.ca/Chicago-Hotels-River-North-Rooftop-With-In-Out-Parking-1.h117712527.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/96000000/95660000/95650200/95650151/83b5c9ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, table tennis](https://images.trvl-media.com/lodging/96000000/95660000/95650200/95650151/ac8ae7eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/96000000/95660000/95650200/95650151/48e35b24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/96000000/95660000/95650200/95650151/31cb6fc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Downtown Chicago

[](https://www.expedia.ca/Chicago-Hotels-Your-Chicago-Get-Away.h95650151.Hotel-Information)

8.4/10

Very good

(8)

"Clean, simple space close to the parks at the waterfront (Millennium, Grant, etc) and several spots for coffee. A bit of an odd building location (it's in a dorm tower with a laundry space next door! Not noisy tho) but easy to access at all hours, nice view as pictured."

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

Pip M.

CA $243

CA $523 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Chicago-Hotels-Your-Chicago-Get-Away.h95650151.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/124000000/123180000/123174400/123174397/d316e969.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/124000000/123180000/123174400/123174397/52004a45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/123180000/123174400/123174397/859e6837.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/124000000/123180000/123174400/123174397/52e00db1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Downtown Chicago

[](https://www.expedia.ca/Chicago-Hotels-Downtown-Chicago-Stay-With-Free-In-Out-Parking-3.h123174397.Hotel-Information)

CA $165

CA $477 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Chicago-Hotels-Downtown-Chicago-Stay-With-Free-In-Out-Parking-3.h123174397.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/fb27e879.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)

![Property grounds](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/4c1d4299.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Downtown Chicago

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

10/10

Exceptional

(1)

"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."

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

Anonymous traveller

CA $87

CA $232 total

includes taxes & fees

Jan 14 - Jan 15, 2026

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

![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117790000/117782400/117782327/58db8883.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, offices](https://images.trvl-media.com/lodging/118000000/117790000/117782400/117782327/92c646c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, offices](https://images.trvl-media.com/lodging/118000000/117790000/117782400/117782327/57cc1f8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/118000000/117790000/117782400/117782327/ce588c2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Near North Side

[](https://www.expedia.ca/Chicago-Hotels-4BR-Modern-Gem-Sleek.h117782327.Hotel-Information)

10/10

Exceptional

(8)

"Great stay. Very clean. Comfortable beds. Great location "

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

shannon u.

CA $866

CA $1,548 total

includes taxes & fees

Dec 18 - Dec 19

[](https://www.expedia.ca/Chicago-Hotels-4BR-Modern-Gem-Sleek.h117782327.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)

### Apartment in Downtown Chicago

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

CA $87

CA $232 total

includes taxes & fees

Jan 1 - Jan 2, 2026

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

![4 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/123000000/122190000/122181300/122181219/26fef3e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/123000000/122190000/122181300/122181219/c4f77266.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/123000000/122190000/122181300/122181219/319be56a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122190000/122181300/122181219/5d728599.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Downtown Chicago

[](https://www.expedia.ca/Chicago-Hotels-Modern-West-Loop-Gem-City-Views-Prime-Location-3.h122181219.Hotel-Information)

10/10

Exceptional

(1)

"The host communicated everything very well. The short videos sent giving info about all the things you'd need to know were super helpful!"

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

Laurie A.

CA $205

CA $529 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Chicago-Hotels-Modern-West-Loop-Gem-City-Views-Prime-Location-3.h122181219.Hotel-Information)

![4 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/123000000/122190000/122181200/122181192/fc67ec22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/123000000/122190000/122181200/122181192/ad43adba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/123000000/122190000/122181200/122181192/0ba6c337.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122190000/122181200/122181192/05db8c76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Downtown Chicago

[](https://www.expedia.ca/Chicago-Hotels-Modern-West-Loop-Gem-City-Views-Prime-Location-5.h122181192.Hotel-Information)

8.0/10

Very good

(1)

"Great location, plenty of space and clean home. "

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

Brittany T.

CA $182

CA $501 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Chicago-Hotels-Modern-West-Loop-Gem-City-Views-Prime-Location-5.h122181192.Hotel-Information)

![Fridge, microwave, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/123000000/122190000/122181300/122181224/3916faf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122190000/122181300/122181224/25e5be06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/123000000/122190000/122181300/122181224/6d69ac98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/123000000/122190000/122181300/122181224/7750e341.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Downtown Chicago

[](https://www.expedia.ca/Chicago-Hotels-Modern-West-Loop-Gem-City-Views-Prime-Location-2.h122181224.Hotel-Information)

10/10

Exceptional

(2)

"Apartment was clean and nice. Nice to have off street parking and the hosts were quick to respond. "

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

Erik R.

CA $226

CA $558 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Chicago-Hotels-Modern-West-Loop-Gem-City-Views-Prime-Location-2.h122181224.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/117000000/116030000/116024600/116024537/4dadbd09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/117000000/116030000/116024600/116024537/92ec7bf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116030000/116024600/116024537/fe7fd7f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116030000/116024600/116024537/5bba47af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Near West Side

[](https://www.expedia.ca/Chicago-Hotels-Spacious-3-Bedroom-Apartment-Near-Downtown.h116024537.Hotel-Information)

9.4/10

Exceptional

(8)

"Nice place to stay. Good communication with the owner."

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

Ryan

CA $94

CA $469 total

includes taxes & fees

Jan 15 - Jan 16, 2026

[](https://www.expedia.ca/Chicago-Hotels-Spacious-3-Bedroom-Apartment-Near-Downtown.h116024537.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101620000/101619100/101619097/3ab1d1bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/102000000/101620000/101619100/101619097/91c8477b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101620000/101619100/101619097/f4be1275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/102000000/101620000/101619100/101619097/a7036b11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Uptown

[](https://www.expedia.ca/Chicago-Hotels-Artistic-Loft-Rooftop-Uptown-Montrose-Beach-GymWFH.h101619097.Hotel-Information)

10/10

Exceptional

(48)

"Clean and quiet, perfect for nights to rest after exploring the city"

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

Joe T.

CA $66

CA $320 total

includes taxes & fees

Jan 12 - Jan 13, 2026

[](https://www.expedia.ca/Chicago-Hotels-Artistic-Loft-Rooftop-Uptown-Montrose-Beach-GymWFH.h101619097.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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Private vacation homes

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Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Winnetka%2C+Illinois%2C+United+States+of+America&regionId=175751&latLong=42.108082%2C-87.735893&adults=2&startDate=2026-03-15&d1=2026-03-15&endDate=2026-03-18&d2=2026-03-18&lodging=APARTMENT)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Winnetka%2C+Illinois%2C+United+States+of+America&regionId=175751&latLong=42.108082%2C-87.735893&adults=2&startDate=2026-03-15&d1=2026-03-15&endDate=2026-03-18&d2=2026-03-18&lodging=VILLA)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Winnetka%2C+Illinois%2C+United+States+of+America&regionId=175751&latLong=42.108082%2C-87.735893&adults=2&startDate=2026-03-15&d1=2026-03-15&endDate=2026-03-18&d2=2026-03-18&lodging=CONDO)

Residences

[](https://www.expedia.ca/Hotel-Search?destination=Winnetka%2C+Illinois%2C+United+States+of+America&regionId=175751&latLong=42.108082%2C-87.735893&adults=2&startDate=2026-03-15&d1=2026-03-15&endDate=2026-03-18&d2=2026-03-18&lodging=RESIDENCE)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Winnetka%2C+Illinois%2C+United+States+of+America&regionId=175751&latLong=42.108082%2C-87.735893&adults=2&startDate=2026-03-15&d1=2026-03-15&endDate=2026-03-18&d2=2026-03-18&lodging=COTTAGE)

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## Top Winnetka Hotel Reviews

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

### Congress Plaza Hotel

10/10 Excellent

"Room was comfortable and clean. Staff was very friendly "

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

![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg)

### Palmer House a Hilton Hotel

10/10 Excellent

"The room was very spacious, the hotel lobby and bar are beautiful. Staff is super friendly and helpful! Would definitely stay here again"

[](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information)

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

### Eurostars Magnificent Mile

10/10 Excellent

"Loved the location and the room was nice with a view!"

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

"Hotel was very nice. Clean and quiet rooms. Good value for the price. Staff was super friendly and overly accommodating during our stay. From the curb service upon arrival, the maintenance man that had to make a minor repair in our room to the bellman that waited at the curb with us to load our bags in the uber. Cannot recommend this hotel enough!"

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

"Very clean and the staff was wonderful!"

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

"Beautiful old hotel convenient to downtown . Wonderful rooms and great onsite dining. You can hear the trains outside from pretty much every room but I found it acceptable noise level. "

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

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

### Swissotel - Chicago

10/10 Excellent

"Great hotel "

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

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

### River Hotel

10/10 Excellent

"The staff was amazing and our room was just as good. Can’t wait to come back!"

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

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

### Hyatt Regency Chicago

10/10 Excellent

"The room view was beautiful! The staff was super attentive and helpful. "

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

## Find out more about Winnetka

## Winnetka Apartments information

| Number of reviews | 112             |
| ----------------- | --------------- |
| Accommodation     | 2241 Apartments |
| Lowest Price      | CA $228         |
| Highest Price     | CA $1,548       |

## Frequently asked questions

### What's it like to stay at an apartment in Winnetka?

### How do you know if an apartment is the best choice for your stay?

### What can I expect from the weather in Winnetka?

### What should I see in Winnetka?

### What's the best way to get to and around Winnetka?

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