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)

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Photo by Steve Luzzo

# Far Southwest Side Vacation Rentals

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## Check prices for these dates

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)

In two months

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248635976475353&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976475353&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976475353&startDate=2026-03-06&endDate=2026-03-08&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

![Indoor pool](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/a9b3121a.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)

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

![Interior](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/1309495b.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)

![TV, offices](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/f72f6088.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gold Coast Living: Modern Studio Unit

Downtown Chicago

10/10

Exceptional

(3)

"Perfect pet friendly pied-à-terre! This sweet studio comes highly recommended!!!!"

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

Brandy

CA $97

CA $232 total

includes taxes & fees

Nov 17 - Nov 18

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/939f8498.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/0ec6dac1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/a9804ae4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/c1cc9a6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sleek 1BR Apt w/ Laundry

Downtown Chicago

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 $104

CA $255 total

includes taxes & fees

Dec 3 - Dec 4

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

![Business Apartment, City View | Private kitchen](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/0374aa13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Apartment, City View | Living area](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/06fff62f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![75-inch Smart TV with digital channels, Netflix, streaming services](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/7fc927d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 4BR Corporate Suite Central and Modern

Near North Side

10/10

Exceptional

(8)

"Great location in Lincoln Park. Easy walk to several shops and restaurants. And about a 5 minute walk to the redline station (North/Clybourn). Very clean and quiet inside the unit. Building is very new. Room access through the Latch app is simple. I would definitely stay here again. The overall experience was excellent and my other guests would agree. "

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

Phillip

CA $268

CA $609 total

includes taxes & fees

Nov 16 - Nov 17

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

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

![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)

### West Loop Living – Bright 1BR

Downtown Chicago

10/10

Exceptional

(1)

"Thorough and easy to follow parking and check in instructions. Clean apartment. "

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

Kira V.

CA $101

CA $251 total

includes taxes & fees

Nov 16 - Nov 17

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

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

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/640a9e62.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)

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

Downtown Chicago

9.4/10

Exceptional

(3)

"Convenient location and clean place"

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

David S.

CA $101

CA $251 total

includes taxes & fees

Nov 17 - Nov 18

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

![Lobby sitting area](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/f7e5c565_edited_04eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 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)

![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)

![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)

![Seasonal outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/cb208a99.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)

![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)

![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)

![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)

### Stylish 1BR in West Loop

Downtown Chicago

10/10

Exceptional

(9)

"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 $101

CA $251 total

includes taxes & fees

Nov 20 - Nov 21

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712536/73f1c663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712536/360842b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712536/a80d9e55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712536/bd271405.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### River North Rooftop With In and Out Parking 5

Downtown Chicago

10/10

Exceptional

(2)

"As advertised. Beautiful, well appointed apartment. Centrally located to restaurants, shopping and the L train. Hosts were very communicative and attentive to our needs. Highly recommend. "

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

Mike S.

CA $178

CA $479 total

includes taxes & fees

Dec 11 - Dec 12

[](https://www.expedia.ca/Chicago-Hotels-River-North-Rooftop-With-In-Out-Parking-5.h117712536.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)

![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)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/6b9648de.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)

### Sun-Drenched 1BR Apartment

Downtown Chicago

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 $101

CA $251 total

includes taxes & fees

Nov 17 - Nov 18

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

![Outdoor dining](https://images.trvl-media.com/lodging/119000000/118410000/118409500/118409489/6818f7ad.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/119000000/118410000/118409500/118409489/92a0def3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118410000/118409500/118409489/56fe72f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Near North Side

10/10

Exceptional

(1)

"Nice place, clean property, great views "

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

Zach L.

CA $198

CA $633 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Chicago-Hotels-High-Rise-4BR-W-Views.h118409489.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/e4296478.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)

![Smart TV](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/489cf83a.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712525/42661a15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712525/4502a11e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712525/aa9373a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712525/21564a39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### South Loop Rooftop With In and Out Parking 3

Downtown Chicago

8.6/10

Excellent

(4)

"Modern and stylish apartment in a great location. Lots of extra thoughtful touches made it a great stay. "

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

Angela M.

CA $154

CA $448 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Chicago-Hotels-South-Loop-Rooftop-With-In-Out-Parking.h117712525.Hotel-Information)

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

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793104/53fb8853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

![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)

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

Downtown Chicago

9.6/10

Exceptional

(13)

"Had a very nice time in Chicago!"

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

Valerie S.

CA $126

CA $310 total

includes taxes & fees

Dec 1 - Dec 2

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

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/123000000/122190000/122181200/122181192/62609cc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern West Loop Gem-City Views & Prime Location 5

Downtown Chicago

CA $215

CA $283 total

includes taxes & fees

Nov 24 - Nov 25

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

![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)

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

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792754/c0215d12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Complete 1BR Home Sum

Downtown Chicago

CA $101

CA $251 total

includes taxes & fees

Nov 16 - Nov 17

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105560000/105552500/105552490/w1350h899x0y1-d7005b5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105560000/105552500/105552490/9aa725fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, video games, offices](https://images.trvl-media.com/lodging/106000000/105560000/105552500/105552490/w1350h899x0y1-19b66913.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/106000000/105560000/105552500/105552490/w1350h899x0y1-beef26b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Little Village

10/10

Exceptional

(8)

"Seriously, very beautiful place to stay like the title of the announce. Cozy and affordable!! I highly recommend if you plan to visit Chicago for a week!"

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

Christian M.

CA $93

CA $296 total

includes taxes & fees

Nov 20 - Nov 21

[](https://www.expedia.ca/Chicago-Hotels-Cozy-Boho-Chicago-10-Min-To-Chicago.h105552490.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)

![Living area](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/5dcfd7fd.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)

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

### Wrigleyville Suites

Lakeview

9.6/10

Exceptional

(25)

"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)

![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121820000/121815200/121815186/b1ada0e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121820000/121815200/121815186/6a00edbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/122000000/121820000/121815200/121815186/d8580e49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Toilet paper](https://images.trvl-media.com/lodging/122000000/121820000/121815200/121815186/0d8c5080.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pleasant 3-bedroom house in Sauk Village

Sauk Village

10/10

Exceptional

(1)

"My Experience Was (NOTHING) Short Of Perfect! The Place Is Nice & The Host Was Even Better! I’ll Forsure Be Booking Again! "

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

Aaron K.

CA $112

CA $188 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Sauk-Village-Hotels-Pleasant-3-Bedroom-House-In-Sauk-Village.h121815186.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)

## Find vacation rentals that suit your style

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Far+Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475353&latLong=41.720804%2C-87.679959&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-16&d2=2026-02-16&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Far+Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475353&latLong=41.720804%2C-87.679959&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-16&d2=2026-02-16&lodging=APARTMENT)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Far+Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475353&latLong=41.720804%2C-87.679959&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-16&d2=2026-02-16&lodging=COTTAGE)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Far+Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475353&latLong=41.720804%2C-87.679959&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-16&d2=2026-02-16&lodging=CONDO)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Far+Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475353&latLong=41.720804%2C-87.679959&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-16&d2=2026-02-16&lodging=VILLA)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Far+Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475353&latLong=41.720804%2C-87.679959&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-16&d2=2026-02-16&lodging=VACATION_HOME)

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

[Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FFar-Southwest-Side-Vacation-Rentals.d553248635976475353.Travel-Guide-VacationRentals)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FFar-Southwest-Side-Vacation-Rentals.d553248635976475353.Travel-Guide-VacationRentals)

## 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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-   [British Columbia Vacation Rentals](https://www.expedia.ca/Destinations-In-British-Columbia.d11117.Vacation-Rental-Destinations)
-   [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 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 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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Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app

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