Title: Far Southwest Side Vacation Rentals from CA $134: Short-Term Rentals for 2025 | Expedia.ca

 

[Far Southwest Side Travel Guide](https://expedia.ca/Far-Southwest-Side.dx553248635976475353)[Hotels in Far Southwest Side](https://expedia.ca/Far-Southwest-Side-Hotels.d553248635976475353.Travel-Guide-Hotels)[Flights to Far Southwest Side](https://expedia.ca/Cheap-Flights-To-Far-Southwest-Side.d553248635976475353.Travel-Guide-Flights)[Far Southwest Side Car Rentals](https://expedia.ca/Car-Rentals-In-Far-Southwest-Side.d553248635976475353.Car-Rental-Guide)[Far Southwest Side Vacation Packages](https://expedia.ca/Far-Southwest-Side.d553248635976475353.Destination-Travel-Guides)

![](https://mediaim.expedia.com/destination/2/c1b10fc2dd618159f972d6db30c06f92.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Steve Luzzo

# Far Southwest Side Vacation Rentals

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## Check prices for these dates

Tonight

[Nov 15 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635976475353&startDate=2025-11-15&endDate=2025-11-16&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Nov 16 - Nov 17](https://www.expedia.ca/Hotel-Search?regionId=553248635976475353&startDate=2025-11-16&endDate=2025-11-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635976475353&startDate=2025-11-21&endDate=2025-11-23&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976475353&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Vacation Rentals in Far Southwest Side

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/114000000/113100000/113092000/113091937/6f237116.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113100000/113092000/113091937/fe065294.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/114000000/113100000/113092000/113091937/4787eb56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113100000/113092000/113091937/ff164355.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### House with garage, outdoor dining and basement bar

Auburn Gresham

8.8/10

Excellent

(6)

"Property was very clean, warm and welcoming. Beds were comfortable. Property manager was great at checking in, and readily available. The place smells great! Everything is new! We will definitely book again!"

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

Jessica M.

[](https://www.expedia.ca/Chicago-Hotels-House-With-Garage.h113091937.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/a9b3121a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/eacd6d88.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)

![Studio, 1 Queen Bed (Studio Apartment) | Private kitchen](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/1bf06d5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sentral Michigan Avenue

Downtown Chicago

9.2/10

Wonderful

(983)

"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "

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

Nicole

CA $166

CA $236 total

includes taxes & fees

Dec 7 - Dec 8

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

![49-inch Smart TV with digital channels, TV, streaming services](https://images.trvl-media.com/lodging/47000000/46240000/46231100/46231022/5915e3d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![City Studio, 1 Queen Bed, Non Smoking, Kitchen (Self Check-in with Virtual Front Desk) | Living area](https://images.trvl-media.com/lodging/47000000/46240000/46231100/46231022/1d34bb7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Living area](https://images.trvl-media.com/lodging/47000000/46240000/46231100/46231022/0ac0f470.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Living area](https://images.trvl-media.com/lodging/47000000/46240000/46231100/46231022/4ebb1bbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kasa Magnificent Mile Chicago

Downtown Chicago

9.2/10

Wonderful

(619)

"Room was very nice, location was wonderful."

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

Nicholas

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

![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)

![Lobby](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/a7a120b4.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)

![Flat-screen TV](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/9bdb478c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Level Chicago – Old Town

Downtown Chicago

9.0/10

Wonderful

(379)

"Property was clean, centrally located with wonderful staff. Will definitely stay again."

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

Michelle

CA $239

CA $312 total

includes taxes & fees

Nov 20 - Nov 21

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

![1 bedroom, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/92000000/91690000/91683200/91683158/e3b8d058.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/92000000/91690000/91683200/91683158/593f3c13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, electric kettle, cookware/dishes/utensils](https://images.trvl-media.com/lodging/92000000/91690000/91683200/91683158/a5314f63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![50-inch flat-screen TV with digital channels, TV, streaming services](https://images.trvl-media.com/lodging/92000000/91690000/91683200/91683158/a9095b05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Downtown Chicago

8.0/10

Very good

(401)

"Quite and low key spot"

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

Shunica

[](https://www.expedia.ca/Sonder-Market-Hall.h91683158.Hotel-Information)

![Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony](https://images.trvl-media.com/lodging/30000000/29440000/29433500/29433443/603af13d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Studio, 1 King Bed, Non Smoking, Kitchen (Self Check-in with Virtual Front Desk) | In-room dining](https://images.trvl-media.com/lodging/30000000/29440000/29433500/29433443/7934883a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | City view](https://images.trvl-media.com/lodging/30000000/29440000/29433500/29433443/24b549c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Studio, 1 King Bed, Non Smoking, Kitchen (Self Check-in with Virtual Front Desk) | City view](https://images.trvl-media.com/lodging/30000000/29440000/29433500/29433443/bfbcc9a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kasa South Loop Chicago

Downtown Chicago

9.4/10

Exceptional

(373)

"An excellent place to stay in Chicago downtown."

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

ABDULHAFEEZ

[](https://www.expedia.ca/Chicago-Hotels-Kasa-South-Loop-Chicago.h29433443.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/99000000/98590000/98589700/98589620/038aeb00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, premium bedding, individually decorated](https://images.trvl-media.com/lodging/99000000/98590000/98589700/98589620/a33c4e00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![50-inch flat-screen TV with digital channels, streaming services](https://images.trvl-media.com/lodging/99000000/98590000/98589700/98589620/de5e0137.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, premium bedding, individually decorated](https://images.trvl-media.com/lodging/99000000/98590000/98589700/98589620/d277fc7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sonder by Marriott Bonvoy The Burnham Apartments Loop

Downtown Chicago

8.8/10

Excellent

(253)

"Great stay. "

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

Teresa

[](https://www.expedia.ca/Chicago-Hotels-Sonder-The-Burnham.h98589620.Hotel-Information)

![36-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/45000000/44780000/44773000/44772938/ccdc9112.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![36-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/45000000/44780000/44773000/44772938/a8e87dd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, individually decorated, individually furnished](https://images.trvl-media.com/lodging/45000000/44780000/44773000/44772938/a811cd1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/45000000/44780000/44773000/44772938/dc543b9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Near South Side

8.6/10

Excellent

(713)

"Love the unit and location close to multiple restaurants and shopping."

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

Jessie

[](https://www.expedia.ca/Chicago-Hotels-Sonder-At-South-Wabash.h44772938.Hotel-Information)

![1 bedroom, individually furnished, desk, iron/ironing board](https://images.trvl-media.com/lodging/84000000/83700000/83695900/83695822/112ab7b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![42-inch flat-screen TV with digital channels, TV, streaming services](https://images.trvl-media.com/lodging/84000000/83700000/83695900/83695822/a5b88630.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, individually furnished, desk, iron/ironing board](https://images.trvl-media.com/lodging/84000000/83700000/83695900/83695822/de34b3e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, individually furnished, desk, iron/ironing board](https://images.trvl-media.com/lodging/84000000/83700000/83695900/83695822/5077246b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sonder by Marriott Bonvoy The Opal Apartments River North

Downtown Chicago

8.4/10

Very good

(57)

"Great location. Apartment had all the amenities needed. Felt safe. Only not so good part was that being in downtown, it wasn't super quiet at times. Would stay here again without a doubt."

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

Swastika

[](https://www.expedia.ca/Chicago-Hotels-Sonder-The-Opal.h83695822.Hotel-Information)

![50-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/65000000/64880000/64871100/64871080/d10a452f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, individually decorated, individually furnished](https://images.trvl-media.com/lodging/65000000/64880000/64871100/64871080/dac97393.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/65000000/64880000/64871100/64871080/36238ab8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![50-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/65000000/64880000/64871100/64871080/851ef6de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Downtown Chicago

8.2/10

Very good

(188)

"Place was amazing! Very centralized, all sorts of restaurants nearby, and right next to the CTA Trains which is AWESOME!"

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

Alexander

[](https://www.expedia.ca/Chicago-Hotels-Sonder-At-Jewelers-Row.h64871080.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/97000000/96300000/96299500/96299486/05d44ec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![50-inch Smart TV with satellite channels](https://images.trvl-media.com/lodging/97000000/96300000/96299500/96299486/79c83288.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![50-inch Smart TV with satellite channels](https://images.trvl-media.com/lodging/97000000/96300000/96299500/96299486/042dd182.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, down comforters, desk](https://images.trvl-media.com/lodging/97000000/96300000/96299500/96299486/f5b85335.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Neighborhood Hotel-Little Italy

Near West Side

9.6/10

Exceptional

(218)

"This hotel is a 10 out of 10 for me! The hotel room was clean and the location was great. When I come back next year I’m definitely coming back here "

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

Amonee

[](https://www.expedia.ca/Chicago-Hotels-The-Neighborhood-Hotel-Little-Italy.h96299486.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/06060406.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/2626f596.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![Living area](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/c25a1316.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wrigleyville Suites

Lakeview

9.4/10

Exceptional

(26)

"Excellent location and very clean! Would stay again!"

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

Jacob

CA $121

CA $142 total

includes taxes & fees

Nov 17 - Nov 18

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

![Business centre](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/825d44e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![BBQ/picnic area](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/860305fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cafe](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/715d8399.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kasa River North Chicago

Downtown Chicago

9.4/10

Exceptional

(177)

"Awesome stay "

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

Sally

CA $188

CA $352 total

includes taxes & fees

Nov 24 - Nov 25

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

![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/740de96f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/e66c238f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/e4296478.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/4c40e70c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chicago luxury home suites

Downtown Chicago

10/10

Exceptional

(1)

"This was Amazing stay I have ever had in my life. Wonderful host, super clean. Stunning views, close to everything that you would needed. "

![New Zealand](https://a.travel-assets.com/egds/marks/flags/nz.svg)

Moha

CA $398

CA $467 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Chicago-Hotels-Chicago-Luxury-Home-Suites.h121424489.Hotel-Information)

![Apartment, 1 Bedroom | Living room](https://images.trvl-media.com/lodging/42000000/41970000/41963600/41963526/1687c774.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/42000000/41970000/41963600/41963526/3e40aa77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 3 Bedrooms](https://images.trvl-media.com/lodging/42000000/41970000/41963600/41963526/4dde9143.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/42000000/41970000/41963600/41963526/26c37847.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sonder by Marriott Bonvoy Greektown Apartments

Downtown Chicago

8.6/10

Excellent

(65)

"I enjoyed my stay! Thanks!"

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

Jonathan

[](https://www.expedia.ca/Chicago-Hotels-Sonder-Greektown-Suites.h41963526.Hotel-Information)

![Comfort Double Room](https://images.trvl-media.com/lodging/113000000/112310000/112306500/112306435/22fe051f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/113000000/112310000/112306500/112306435/81879fe3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Studio](https://images.trvl-media.com/lodging/113000000/112310000/112306500/112306435/d6f1cd2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Double Room](https://images.trvl-media.com/lodging/113000000/112310000/112306500/112306435/11a11fca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Harvey

3.8/10

(67)

"This place looked like a whole in the wall I didn’t even stay the place was so dirty and I could not receive a refund looks disgusting and not even worth a $50 stay at minimum. "

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

Bria

CA $119

CA $134 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Chicago-Hotels-Comfort-Inn-Chicago-Wind-Creek-Casino.h112306435.Hotel-Information)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792882/9262cfe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792882/631182fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792882/f361fe8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792882/w1024h1011x0y0-4b62d70e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Clean & Equipped 1BR Apt

Lakeview

9.2/10

Wonderful

(34)

"Was very clean and comfortable simply furnished but nice close to the things we were looking for. "

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

zack r.

CA $84

CA $231 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Chicago-Hotels-Clean-Equipped-1BR-Apt.h116792882.Hotel-Information)

![Classic Apartment | Private kitchen](https://images.trvl-media.com/lodging/120000000/119980000/119973600/119973593/65b6e2ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Apartment | Living area](https://images.trvl-media.com/lodging/120000000/119980000/119973600/119973593/2b79b031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Apartment | Bathroom](https://images.trvl-media.com/lodging/120000000/119980000/119973600/119973593/82b5fa12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Apartment](https://images.trvl-media.com/lodging/120000000/119980000/119973600/119973593/w2571h1446x1y1-ccdca671.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish Apartment near Chicago Downtown

Bridgeport

CA $330

CA $533 total

includes taxes & fees

Nov 17 - Nov 18

[](https://www.expedia.ca/Chicago-Hotels-Stylish-Apartment-Near-Chicago-Downtown.h119973593.Hotel-Information)

![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792603/2c5edc73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792603/ac888596.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792603/0a34dfde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792603/77ca5eb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Studio in Hyde Park-Walk to Lake & University

Hyde Park

8.8/10

Excellent

(10)

"Good communication and easy check-in"

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

Chen

CA $91

CA $226 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Chicago-Hotels-Cozy-Studio-In-Hyde-Park-Walk-To-Lake-University.h116792603.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792894/de39e34a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792894/d4ca51dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792894/978fa548.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792894/755fde52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lakeview 2BR Apartment

Lakeview

9.4/10

Exceptional

(24)

"Had a great weekend! The listing is accurate and is in a great location! We did have an issue with one room because of a storm from the night before, but I contacted the hosts and they responded immediately and fixed the problem within a few hours. I would recommend this rental to friends and family!"

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

Jessica H.

CA $84

CA $252 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Chicago-Hotels-Lakeview-2BR-Apartment.h116792894.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=2025-11-29&endDate=2025-11-30&regionId=553248635976475353&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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

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## Top Far Southwest Side Hotel Reviews

### Hotel Riu Plaza Chicago

10/10 Excellent

"Beautiful new hotel. Amazing rooms and exceptional service. Best breakfast I have had at a hotel."

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

### Freehand Chicago

10/10 Excellent

"Super friendly and helpful staff, environment felt warm and welcoming. The people who stay there are pretty cool as well! Rooms were clean and cozy. Would definitely stay there again if I’m in Chicago again."

[](https://expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information)

### Eurostars Magnificent Mile

10/10 Excellent

"The staff was so helpful and friendly!!!! "

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

### The Wade

10/10 Excellent

"Staff was welcoming! We appreciated the engineering team for stepping in and helping us out! He was kind. Would stay again! "

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

### Hotel Felix River North/Magnificent Mile

10/10 Excellent

"The customer service top tier!!! The rooms were extremely small but they were clean. Staff was very helpful. "

[](https://expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information)

### The Whitehall Hotel, BW Premier Collection

10/10 Excellent

"Centrally located by the Magnificent Mile. Plenty of shopping options. Access to both train and bus public transportation. Hotel is older but kept. Staff are friendly, efficient, abd aware of comings and goings. Always greeting you ss you leave snd return. Rooms and property are clean. Rooms are spacious for a large metro city. I have stayed at this location multiple times. Will always be my first choice. "

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

### Hilton Chicago

10/10 Excellent

"It was the swankiest joint I ever strayed in! I upgraded for $40 and had a room with a view of Lake Michigan! They had three restaurants/bars right in the hotel!!"

[](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information)

### Aloft Chicago Mag Mile

10/10 Excellent

"Everything was phenomenal with our stay. The staff went above and beyond to make our trip to Chicago a special one. I would recommend this hotel to ANYONE looking to visit the area. Looking forward to visiting again one day! "

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

### citizenM Chicago Downtown

10/10 Excellent

"Modern, super European, petite but very "

[](https://expedia.ca/Chicago-Hotels-CitizenM-Chicago-Downtown.h82652306.Hotel-Information)

## Find out more about Far Southwest Side

**Everything you need to know about** **Far Southwest Side** **vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Far Southwest Side vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on!

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

**Far Southwest Side vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Far Southwest Side. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Far Southwest Side vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Far Southwest Side vacation rentals we have selected for you start as low as CA $134 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on Far Southwest Side rentals**

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

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

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

## Explore a world of travel with Expedia

-   Trending destinations on Expedia.ca
-   All accommodation types in Far Southwest Side

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-   [Apartments in Far Southwest Side](https://expedia.ca/Far-Southwest-Side-Apartments.d553248635976475353-aaApartments.Travel-Guide-Accommodation)
-   [Vacation Homes in Far Southwest Side](https://expedia.ca/Far-Southwest-Side-Private-Vacation-Homes.d553248635976475353-aaPrivateVacationHomes.Travel-Guide-Accommodation)
-   [Condo Rentals in Far Southwest Side](https://expedia.ca/Far-Southwest-Side-Condos.d553248635976475353-aaCondos.Travel-Guide-Accommodation)
-   [Motels in Far Southwest Side](https://expedia.ca/Far-Southwest-Side-Motels.d553248635976475353-aaMotels.Travel-Guide-Accommodation)
-   [Aparthotels in Far Southwest Side](https://expedia.ca/Far-Southwest-Side-Apart-Hotels.d553248635976475353-aaApartHotels.Travel-Guide-Accommodation)
-   [B&B in Far Southwest Side](https://expedia.ca/Far-Southwest-Side-Bed-And-Breakfast.d553248635976475353-aaBedAndBreakfast.Travel-Guide-Accommodation)
-   [Cottages in Far Southwest Side](https://expedia.ca/Far-Southwest-Side-Cottages.d553248635976475353-aaCottages.Travel-Guide-Accommodation)
-   [Guest Houses in Far Southwest Side](https://expedia.ca/Far-Southwest-Side-Guest-Houses.d553248635976475353-aaGuestHouses.Travel-Guide-Accommodation)
-   [Hostels in Far Southwest Side](https://expedia.ca/Far-Southwest-Side-Hostels.d553248635976475353-aaHostels.Travel-Guide-Accommodation)
-   [Resorts in Far Southwest Side](https://expedia.ca/Far-Southwest-Side-Resort-Hotels.d553248635976475353-aaResortHotels.Travel-Guide-Accommodation)
-   [Villas in Far Southwest Side](https://expedia.ca/Far-Southwest-Side-Villas.d553248635976475353-aaVillas.Travel-Guide-Accommodation)
-   [Cabin Rentals in Far Southwest Side](https://expedia.ca/Far-Southwest-Side-Cabins.d553248635976475353-aaCabins.Travel-Guide-Accommodation)

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-   [Flights from Vancouver (YVR) to Calgary (YYC)](https://expedia.ca/lp/flights/yvr/yyc/vancouver-to-calgary)
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-   [Flights to Vancouver](https://expedia.ca/Cheap-Flights-To-Vancouver.d178315.Travel-Guide-Flights)
-   [Flights from Vancouver (YVR) to Aluva (COK)](https://expedia.ca/lp/flights/yvr/cok/vancouver-to-cochin)

Packages

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-   [Grant Park](https://expedia.ca/Grant-Park-Downtown-Chicago.d507389.Vacation-Attraction)

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![QR code to download the app](data:image/png;base64,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)