Title: South Side Vacation Rentals from CA $247: Short-Term Rentals for 2026 | Expedia.ca

[South Side Travel Guide](https://expedia.ca/South-Side.dx553248635074842823)[Hotels in South Side](https://expedia.ca/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels)[Flights to South Side](https://expedia.ca/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights)[Things to do in South Side](https://expedia.ca/Things-To-Do-In-South-Side.d553248635074842823.Travel-Guide-Activities)[South Side Car Rentals](https://expedia.ca/Car-Rentals-In-South-Side.d553248635074842823.Car-Rental-Guide)[South Side Vacation Packages](https://expedia.ca/South-Side.d553248635074842823.Destination-Travel-Guides)

![Chicago South Side](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 26 - Jun 28](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for South Side vacation rentals

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117130000/117124300/117124263/88a6a75b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/118000000/117130000/117124300/117124263/fc07c1c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/118000000/117130000/117124300/117124263/6dd78f04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117130000/117124300/117124263/8074f855.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Charm Studio Apt in Chicago

[](https://www.expedia.ca/Chicago-Hotels-Cozy-Charm-Studio-Apt-In-Chicago.h117124263.Hotel-Information)

Hyde Park

10/10

Exceptional

(4 reviews)

"Everying was great."

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

Ryan D.

CA $112

CA $249 total

includes taxes & fees

Mar 5 - Mar 6

[](https://www.expedia.ca/Chicago-Hotels-Cozy-Charm-Studio-Apt-In-Chicago.h117124263.Hotel-Information)

![Smart TV, video games](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/w1350h899x0y1-166f73c9.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/92000000/91090000/91086500/91086437/w1350h899x0y1-43718ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/w1350h899x0y1-09740a6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/w1278h1921x2y2-bce03282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

[](https://www.expedia.ca/Chicago-Hotels-Sunflower-Apt-10-Min-From-Downtown-Chicago-Sleeps-Up-To-6.h91086437.Hotel-Information)

Brighton Park

8.6/10

Excellent

(21 reviews)

"Clean and nice. My son loved the arcade game. Would stay again "

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

Nichole S.

[](https://www.expedia.ca/Chicago-Hotels-Sunflower-Apt-10-Min-From-Downtown-Chicago-Sleeps-Up-To-6.h91086437.Hotel-Information)

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793083/ba9db8cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793083/a44fb78b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793083/115c3685.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793083/19ac687a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Studio Unit Near UChicago

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

Hyde Park

8.8/10

Excellent

(15 reviews)

"Clean room and convenient location! "

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

Gabriela

CA $112

CA $247 total

includes taxes & fees

Mar 11 - Mar 12

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

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792489/cf195af6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792489/fe86e080.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792489/f6353a19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, shampoo](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792489/7d0f8c07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sleek & Functional 2-Bedroom Apt

[](https://www.expedia.ca/Chicago-Hotels-Sleek-Functional-2-Bedroom-Apt.h116792489.Hotel-Information)

Hyde Park

9.6/10

Exceptional

(4 reviews)

"Nice place for a girls trip weekend. "

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

Madonna A.

CA $120

CA $299 total

includes taxes & fees

Mar 17 - Mar 18

[](https://www.expedia.ca/Chicago-Hotels-Sleek-Functional-2-Bedroom-Apt.h116792489.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/123000000/122590000/122582000/122581902/w1432h1080x94y0-5a95ad03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/123000000/122590000/122582000/122581902/w1433h1080x93y0-253226e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122590000/122582000/122581902/w1432h1080x94y0-bd552f28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122590000/122582000/122581902/w1432h1080x94y0-7ee1aa63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Near Lake and Museum • Modern • Game Area

[](https://www.expedia.ca/Chicago-Hotels-Walk-To-The-Lake-Grill.h122581902.Hotel-Information)

South Shore

CA $119

CA $737 total

includes taxes & fees

Mar 8 - Mar 9

[](https://www.expedia.ca/Chicago-Hotels-Walk-To-The-Lake-Grill.h122581902.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792457/75d1dc95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792457/0d5faef2.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/117000000/116800000/116792500/116792457/5f21f45c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792457/c4d843cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bright 1BR Unit in a Prime Spot

[](https://www.expedia.ca/Chicago-Hotels-Modern-1BR-Gem-In-Chicago-Kenwood-501.h116792457.Hotel-Information)

Hyde Park

10/10

Exceptional

(1 review)

"We had a great stay. Location is in nice neighborhood with walking access to restaurants and university of Chicago. Apartment was clean and as pictured. Would stay again!!"

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

christine m.

CA $120

CA $275 total

includes taxes & fees

Mar 9 - Mar 10

[](https://www.expedia.ca/Chicago-Hotels-Modern-1BR-Gem-In-Chicago-Kenwood-501.h116792457.Hotel-Information)

![Game room](https://images.trvl-media.com/lodging/97000000/96480000/96479300/96479287/w1350h899x0y1-b9b7a110.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/97000000/96480000/96479300/96479287/w1350h899x0y1-7f0cda99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, video games](https://images.trvl-media.com/lodging/97000000/96480000/96479300/96479287/w1350h899x0y1-24e41c53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96480000/96479300/96479287/w1349h899x1y1-922f1c40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

[](https://www.expedia.ca/Chicago-Hotels-W-Pershing-Large-Chicago-Apt-3-Bed-12-Min-Downtown-Arcade.h96479287.Hotel-Information)

Brighton Park

9.4/10

Exceptional

(9 reviews)

"Great location, spacious, and family friendly. Had cousins over and they had a blast playing the video games. "

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

Jessica H.

CA $120

CA $391 total

includes taxes & fees

Mar 17 - Mar 18

[](https://www.expedia.ca/Chicago-Hotels-W-Pershing-Large-Chicago-Apt-3-Bed-12-Min-Downtown-Arcade.h96479287.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792510/ade3903c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792510/4be03a43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792510/44b6757f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792510/d9c88430.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private 1BR Haven in a Prime Area

[](https://www.expedia.ca/Chicago-Hotels-Chic-Retreat-Cozy-1BR-Apartment.h116792510.Hotel-Information)

Hyde Park

9.0/10

Wonderful

(7 reviews)

"Our stay was very nice, with simple checkin / check out, and excellent communication by our host. "

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

Tom B.

CA $120

CA $275 total

includes taxes & fees

Mar 9 - Mar 10

[](https://www.expedia.ca/Chicago-Hotels-Chic-Retreat-Cozy-1BR-Apartment.h116792510.Hotel-Information)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793049/eb91a024.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793049/0aa9ff95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793049/5468a792.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793049/41851f52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Studio Apt Comfy & Sunlit

[](https://www.expedia.ca/Chicago-Hotels-Studio-Apt-Comfy-Sunlit.h116793049.Hotel-Information)

Hyde Park

10/10

Exceptional

(2 reviews)

"My stay was really good"

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

Paramita B.

CA $112

CA $264 total

includes taxes & fees

Mar 9 - Mar 10

[](https://www.expedia.ca/Chicago-Hotels-Studio-Apt-Comfy-Sunlit.h116793049.Hotel-Information)

![WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792451/24fa79a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792451/0cb68b63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, toaster](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792451/c67dc51a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792451/2bf9ca15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Trendy Studio in Vibrant Area

[](https://www.expedia.ca/Chicago-Hotels-Trendy-Studio-In-Vibrant-Area.h116792451.Hotel-Information)

Hyde Park

CA $112

CA $247 total

includes taxes & fees

Mar 11 - Mar 12

[](https://www.expedia.ca/Chicago-Hotels-Trendy-Studio-In-Vibrant-Area.h116792451.Hotel-Information)

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792640/baa800c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792640/593e7f04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792640/5aadcaf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792640/d08e72d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Smart Stay in Hyde Park 1BR

[](https://www.expedia.ca/Chicago-Hotels-Smart-Stay-In-Hyde-Park-1BR.h116792640.Hotel-Information)

Hyde Park

CA $120

CA $275 total

includes taxes & fees

Mar 10 - Mar 11

[](https://www.expedia.ca/Chicago-Hotels-Smart-Stay-In-Hyde-Park-1BR.h116792640.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792556/f4001857.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792556/ccb9df18.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/117000000/116800000/116792600/116792556/b065d305.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792556/61a4970b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Explore Hyde Park: 2BR Apartment on Blackstone Ave

[](https://www.expedia.ca/Chicago-Hotels-Explore-Hyde-Park-2BR-Apt-On-Blackstone-Ave.h116792556.Hotel-Information)

Hyde Park

7.0/10

Good

(7 reviews)

"All the necessities with no personal touches. Keys from lockbox to open second door were not needed as the second door is always open. Impeccable communication with host. Great location, close to restaurants and train to Millennium Station. Coffee service was excellent, just be sure to find extra pouches in cabinet. Bathtub faucet could not be turned far enough to prevent leaking. TV remote not great and I couldn’t get CNN or MSNBC. I’d stay here again. "

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

lost whale press

CA $120

CA $299 total

includes taxes & fees

Mar 9 - Mar 10

[](https://www.expedia.ca/Chicago-Hotels-Explore-Hyde-Park-2BR-Apt-On-Blackstone-Ave.h116792556.Hotel-Information)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793062/w1536h1012x0y0-b81df5b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793062/4eb1fb3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793062/ba76d560.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793062/4472d85b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bright & Cozy 1BR Near UChicago

[](https://www.expedia.ca/Chicago-Hotels-Bright-Cozy-1BR-Near-UChicago.h116793062.Hotel-Information)

Hyde Park

9.4/10

Exceptional

(3 reviews)

"This apartment is a very basic rental unit – – had what we needed for our three nights stay, and we were very pleased. Great value for the money."

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

Alan F.

CA $120

CA $275 total

includes taxes & fees

Mar 9 - Mar 10

[](https://www.expedia.ca/Chicago-Hotels-Bright-Cozy-1BR-Near-UChicago.h116793062.Hotel-Information)

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792582/f869465d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792582/dc03e46f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792582/c647fd4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792582/7e60538d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Studio Unit | Chic + Prime Location

[](https://www.expedia.ca/Chicago-Hotels-Studio-Unit-Chic-Prime-Location.h116792582.Hotel-Information)

Hyde Park

10/10

Exceptional

(3 reviews)

"Location was just perfect!"

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

Meg D.

CA $112

CA $247 total

includes taxes & fees

Mar 18 - Mar 19

[](https://www.expedia.ca/Chicago-Hotels-Studio-Unit-Chic-Prime-Location.h116792582.Hotel-Information)

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792588/w1020h768x4y0-83536ece.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792588/w1019h768x5y0-94f2c785.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792588/b0554812.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792588/ca996652.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Well-Equipped Studio Apartment

[](https://www.expedia.ca/Chicago-Hotels-Cozy-Well-Equipped-Studio-Apt.h116792588.Hotel-Information)

Hyde Park

CA $112

CA $247 total

includes taxes & fees

Mar 11 - Mar 12

[](https://www.expedia.ca/Chicago-Hotels-Cozy-Well-Equipped-Studio-Apt.h116792588.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/104000000/103330000/103320500/103320435/w1350h899x0y1-cb7026b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/104000000/103330000/103320500/103320435/w1349h899x1y1-88a95071.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103330000/103320500/103320435/w1349h899x1y1-aea79261.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/104000000/103330000/103320500/103320435/w1349h899x1y1-0f9df4ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

[](https://www.expedia.ca/Chicago-Hotels-Spacious-3-Bedroom-Apartment-10-Minutes-To-Downtown-Sleeps-Up-To-10.h103320435.Hotel-Information)

Brighton Park

10/10

Exceptional

(1 review)

"Family-friendly, quiet, perfect for a family or friends vacationing in Chicago. The apartment is very clean and the host was always available and responded quickly. The next time I come to Chicago, i will definitely stay at the apartment \[if available\]. "

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

Fabian H.

CA $104

CA $370 total

includes taxes & fees

Mar 16 - Mar 17

[](https://www.expedia.ca/Chicago-Hotels-Spacious-3-Bedroom-Apartment-10-Minutes-To-Downtown-Sleeps-Up-To-10.h103320435.Hotel-Information)

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792547/890d5e59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792547/3cf8066f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792547/6190912f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792547/df59edea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sunlit & Chic 2BR Retreat

[](https://www.expedia.ca/Chicago-Hotels-Contemporary-2BR-Apartment-In-Vibrant-Hyde-Park.h116792547.Hotel-Information)

Hyde Park

10/10

Exceptional

(2 reviews)

"Great location in Hyde Park! Super clean and comfortable. Bus stop by the front door and walkable to so many things we wanted to do! "

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

Allison K.

CA $120

CA $299 total

includes taxes & fees

Mar 11 - Mar 12

[](https://www.expedia.ca/Chicago-Hotels-Contemporary-2BR-Apartment-In-Vibrant-Hyde-Park.h116792547.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792479/159edb18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792479/48479517.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792479/58e9964d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792479/e5e77513.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bright & Modern 1BR in a Prime Area

[](https://www.expedia.ca/Chicago-Hotels-Bright-Modern-1BR-In-Hyde-Park.h116792479.Hotel-Information)

Hyde Park

8.8/10

Excellent

(3 reviews)

"Property was very clean. We enjoyed ourselves, Thank you!"

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

Charles S.

CA $120

CA $275 total

includes taxes & fees

Mar 10 - Mar 11

[](https://www.expedia.ca/Chicago-Hotels-Bright-Modern-1BR-In-Hyde-Park.h116792479.Hotel-Information)

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792613/7e0b7a84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792613/f0b2b35a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792613/w1196h800x4y0-66d9df7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792613/0b1f4ad5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Trendy Studio Apartment in Chicago

[](https://www.expedia.ca/Chicago-Hotels-Trendy-Studio-Apartment-In-Chicago.h116792613.Hotel-Information)

Hyde Park

8.0/10

Very good

(3 reviews)

"Loved my two-night stay here. The apartment was spotless, quiet, and in the perfect location for my UChicago visit. Check-in info arrived a bit later than expected, but communication overall was thoughtful and helpful, and everything worked out smoothly. Would happily stay again."

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

Helmut P.

CA $112

CA $247 total

includes taxes & fees

Mar 11 - Mar 12

[](https://www.expedia.ca/Chicago-Hotels-Trendy-Studio-Apartment-In-Chicago.h116792613.Hotel-Information)

![4 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792423/327989d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792423/235673cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792423/8f43eb0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792423/fb5bad1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish 4BR South Loop Home

[](https://www.expedia.ca/Chicago-Hotels-Stylish-4BR-South-Loop-Home.h116792423.Hotel-Information)

Greater Grand Crossing

10/10

Exceptional

(2 reviews)

"Very happy with stay. Good communication from property host. "

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

Nicole E.

CA $150

CA $526 total

includes taxes & fees

Mar 10 - Mar 11

[](https://www.expedia.ca/Chicago-Hotels-Stylish-4BR-South-Loop-Home.h116792423.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-03-18&endDate=2026-03-19&regionId=553248635074842823&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## 

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Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=VR_SPRING_PROMO_553248635074842823)

## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=CABIN)

Cottages

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Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=APART_HOTEL)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=VILLA)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=APARTMENT)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=CONDO)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=VACATION_HOME)

Residences

[](https://www.expedia.ca/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=RESIDENCE)

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## Top South Side Hotel Reviews

![Jaslin Hotel](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg)

### Jaslin Hotel

10/10 Excellent

"Great room "

[](https://expedia.ca/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information)

![Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG](https://images.trvl-media.com/lodging/1000000/210000/201300/201281/e8f8e393_y.jpg)

### Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

10/10 Excellent

"Clean and quiet!"

[](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Express-Hotel-Suites-Chicago-Midway-Airport.h201281.Hotel-Information)

![SpringHill Suites by Marriott Chicago Chinatown](https://images.trvl-media.com/lodging/65000000/64630000/64624400/64624399/575b0923_y.jpg)

### SpringHill Suites by Marriott Chicago Chinatown

10/10 Excellent

"Great room and service"

[](https://expedia.ca/Chicago-Hotels-SpringHill-Suites-By-Marriott-Chicago-Chinatown.h64624399.Hotel-Information)

![Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!](https://images.trvl-media.com/lodging/74000000/73640000/73639200/73639173/c0eeff3c_y.jpg)

### Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!

10/10 Excellent

"I can't recommend it enough! The communication with the host was excellent throughout my stay. They were accommodating and even allowed me to stay an extra hour, which made my departure much easier. The location was perfect, and the amenities were just as described. I will definitely be returning to this rental on my next visit to Chicago!"

[](https://expedia.ca/Chicago-Hotels-Comfy-4-Bedroom-Apartment-In-The-Center-Of-CHICAGO-15-Mins-From-Downtown.h73639173.Hotel-Information)

![Hyatt Place Chicago-South/University Medical Center](https://images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/722a9f0a_y.jpg)

### Hyatt Place Chicago-South/University Medical Center

10/10 Excellent

"The staff is always amazing!"

[](https://expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information)

![Admiral Motel By Oyo Chicago I-94](https://images.trvl-media.com/lodging/113000000/112490000/112484100/112484089/cdb6bc21_y.jpg)

### Admiral Motel By Oyo Chicago I-94

10/10 Excellent

"Their customer service has improved DRAMATICALLY since the last time I stayed here. The older black woman working the front desk was quick, courteous and efficient. "

[](https://expedia.ca/Chicago-Hotels-Admiral-Motel-By-Oyo-Chicago-I-94.h112484089.Hotel-Information)

![Chicago Marriott Midway](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/7cf4bf83_y.jpg)

### Chicago Marriott Midway

10/10 Excellent

"Was great ! "

[](https://expedia.ca/Chicago-Hotels-Chicago-Marriott-Midway.h892168.Hotel-Information)

![Sophy Hyde Park](https://images.trvl-media.com/lodging/23000000/22360000/22355300/22355297/f1fd01e1_y.jpg)

### Sophy Hyde Park

10/10 Excellent

"Clean room. Great location for Hyde park and uchicago. "

[](https://expedia.ca/Chicago-Hotels-Sophy-Hyde-Park.h22355297.Hotel-Information)

![Motel 6 - Chicago, IL](https://images.trvl-media.com/lodging/116000000/115880000/115871700/115871645/b32fc0e7_y.jpg)

### Motel 6 - Chicago, IL

10/10 Excellent

"Mrs Wilson is the best"

[](https://expedia.ca/Chicago-Hotels-Motel-6-Chicago.h115871645.Hotel-Information)

## Find out more about South Side

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with South Side. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

## Explore a world of travel with Expedia

- Trending destinations on Expedia.ca
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- [Apartments in South Side ](https://expedia.ca/South-Side-Apartments.d553248635074842823-aaApartments.Travel-Guide-Accommodation)
- [Vacation Homes in South Side ](https://expedia.ca/South-Side-Private-Vacation-Homes.d553248635074842823-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Condo Rentals in South Side ](https://expedia.ca/South-Side-Condos.d553248635074842823-aaCondos.Travel-Guide-Accommodation)
- [Motels in South Side ](https://expedia.ca/South-Side-Motels.d553248635074842823-aaMotels.Travel-Guide-Accommodation)
- [Guest Houses in South Side ](https://expedia.ca/South-Side-Guest-Houses.d553248635074842823-aaGuestHouses.Travel-Guide-Accommodation)
- [Aparthotels in South Side ](https://expedia.ca/South-Side-Apart-Hotels.d553248635074842823-aaApartHotels.Travel-Guide-Accommodation)

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Cars

- [Enterprise Car Rentals In West Side](https://expedia.ca/Enterprise-Car-Rentals-In-West-Side.d553248635976475400-c15.Car-Rental-Guide-Suppliers)
- [Dollar Rent A Car Car Rentals In Central Chicago](https://expedia.ca/Dollar-Rent-A-Car-Car-Rentals-In-Central-Chicago.d553248635976475413-c43.Car-Rental-Guide-Suppliers)

Packages

- [Art Institute of Chicago](https://expedia.ca/Art-Institute-Of-Chicago-Downtown-Chicago.d6064021.Vacation-Attraction)
- [United Center](https://expedia.ca/United-Center-Near-West-Side.d6064077.Vacation-Attraction)
- [Navy Pier](https://expedia.ca/Navy-Pier-Downtown-Chicago.d6069215.Vacation-Attraction)
- [Lincoln Park Zoo](https://expedia.ca/Lincoln-Park-Zoo-Lincoln-Park.d6065147.Vacation-Attraction)
- [Chicago Riverwalk](https://expedia.ca/Chicago-Riverwalk-Downtown-Chicago.d553248621533116610.Vacation-Attraction)
- [Willis Tower](https://expedia.ca/Willis-Tower-Downtown-Chicago.d6064069.Vacation-Attraction)
- [875 North Michigan Avenue](https://expedia.ca/875-North-Michigan-Avenue-Downtown-Chicago.d6065131.Vacation-Attraction)
- [Robie House](https://expedia.ca/Robie-House-Hyde-Park.d6064059.Vacation-Attraction)
- [Griffin Museum of Science and Industry](https://expedia.ca/Griffin-Museum-Of-Science-And-Industry-Hyde-Park.d6064043.Vacation-Attraction)
- [Millennium Park](https://expedia.ca/Millennium-Park-Downtown-Chicago.d6069201.Vacation-Attraction)
- [Water Tower Place](https://expedia.ca/Water-Tower-Place-Downtown-Chicago.d6064087.Vacation-Attraction)
- [Wrigley Field](https://expedia.ca/Wrigley-Field-Lakeview.d6034754.Vacation-Attraction)
- [Grant Park](https://expedia.ca/Grant-Park-Downtown-Chicago.d507389.Vacation-Attraction)

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