Title: South Side Vacation Rentals from CA $232: Short-Term Rentals for 2025 | Expedia.ca

 

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# South 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=553248635074842823&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=553248635074842823&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=553248635074842823&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=553248635074842823&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 South Side

![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)

![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)

![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)

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

Hyde Park

9.0/10

Wonderful

(9)

"Good communication and easy check-in"

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

Chen

CA $97

CA $232 total

includes taxes & fees

Nov 11 - Nov 12

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

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793083/4efcd15b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793083/1a4d0483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793083/d10b773f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793083/829bcf7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Studio Near UChicago

Hyde Park

9.4/10

Exceptional

(9)

"Clean room and convenient location! "

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

Gabriela

CA $97

CA $232 total

includes taxes & fees

Nov 11 - Nov 12

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

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793085/de22ad61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793085/b97e6643.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793085/0149089d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793085/3c0301b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern 1BR in Historic HydePark

Hyde Park

8.4/10

Very good

(8)

"Comfortable space. All the necessary amenities. Extremely walkable to everything.Will stay again. "

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

jasmine h.

CA $101

CA $251 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Chicago-Hotels-Modern-1BR-In-Historic-HydePark.h116793085.Hotel-Information)

![Classic Apartment | Private kitchen](https://images.trvl-media.com/lodging/120000000/119980000/119973600/119973593/5c39d4dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Apartment | Bathroom](https://images.trvl-media.com/lodging/120000000/119980000/119973600/119973593/15271305.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)

![Comfort Apartment | Living area](https://images.trvl-media.com/lodging/120000000/119980000/119973600/119973593/6737cfbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish Apartment near Chicago Downtown

Bridgeport

CA $341

CA $546 total

includes taxes & fees

Nov 11 - Nov 12

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

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792510/a4c1202d.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/ec4a8eac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792510/bd8f40a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792510/f2aa28b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chic Retreat: Cozy 1BR Apartment

Hyde Park

10/10

Exceptional

(4)

"Very quiet and comfortable. Right in the heart of Hyde Park. 10 min walk to Lake Michigan.Clean and well suited for your needs. Would gladly stay again!"

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

Harold M.

CA $101

CA $251 total

includes taxes & fees

Nov 11 - Nov 12

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

![Dining](https://images.trvl-media.com/lodging/118000000/117800000/117794900/117794818/00965c86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117800000/117794900/117794818/c329dc83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/118000000/117800000/117794900/117794818/5058bb1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117800000/117794900/117794818/a501af6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly

South Chicago

10/10

Exceptional

(1)

"Clean apartment and great communication with host. Fixed any small problems very quickly. "

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

Catherine F.

[](https://www.expedia.ca/Chicago-Hotels-South-Shore-Chicago-Condo-1-Block-To-Lake-WiFi-AC-Elevator-420-Friendly.h117794818.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70890000/70886100/70886010/03d3c9c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/71000000/70890000/70886100/70886010/a351b4ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/71000000/70890000/70886100/70886010/554617f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/71000000/70890000/70886100/70886010/2ff2c471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### LakeHouse

South Shore

9.4/10

Exceptional

(23)

"Nice place, everything clean, the only downside is parking"

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

quy u.

[](https://www.expedia.ca/Chicago-Hotels-LakeHouse.h70886010.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/102000000/101330000/101326400/101326333/032f24a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/102000000/101330000/101326400/101326333/5e65af9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/102000000/101330000/101326400/101326333/bcd8e308.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101330000/101326400/101326333/7b79eb91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Chic Urban Oasis Near the Lake!

South Shore

8.0/10

Very good

(7)

"Great property in not the best part of town. "

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

Scott S.

[](https://www.expedia.ca/Chicago-Hotels-The-Chic-Urban-Oasis-Near-The-Lake.h101326333.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792582/7e60538d.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/117000000/116800000/116792600/116792582/f869465d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792582/934676b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792582/032eb104.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Studio Unit | Chic + Prime Location

Hyde Park

CA $97

CA $232 total

includes taxes & fees

Nov 17 - Nov 18

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

![Smart TV](https://images.trvl-media.com/lodging/20000000/19920000/19910400/19910341/w1400h931x0y11-d49c09e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/20000000/19920000/19910400/19910341/4b5ae36b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/20000000/19920000/19910400/19910341/270-20b1b0d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior detail](https://images.trvl-media.com/lodging/20000000/19920000/19910400/19910341/w1400h1046x0y8-fd7bc2b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum

Bronzeville

9.6/10

Exceptional

(73)

"Enough room for a quick get away"

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

wendy C.

[](https://www.expedia.ca/Chicago-Hotels-Spacious-Bronzeville-Gem-Garden-Lvl-Near-Downtown.h19910341.Hotel-Information)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/104000000/103770000/103763600/103763530/w1008h683x16y0-fcd8234f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103770000/103763600/103763530/a3e79335.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Towels, soap, shampoo](https://images.trvl-media.com/lodging/104000000/103770000/103763600/103763530/w1012h683x12y0-1579e12b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103770000/103763600/103763530/10a183f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Toca Bella ~ 7mins to Downtown

Bronzeville

9.8/10

Exceptional

(19)

"Enjoyed my stay. "

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

Thomas M.

[](https://www.expedia.ca/Chicago-Hotels-Toca-Bella-7mins-To-Downtown.h103763530.Hotel-Information)

![Fridge, microwave, oven, coffee/tea maker](https://images.trvl-media.com/lodging/104000000/103280000/103277000/103276998/699a08a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/104000000/103280000/103277000/103276998/8a220ed3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/104000000/103280000/103277000/103276998/147b77ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/104000000/103280000/103277000/103276998/3c86e3c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfortable Condo in the Heart of Bronzeville by RedAwning

Bronzeville

7.2/10

Good

(5)

"From a failed lock that would not open with the correct code at 10:30 at night and it taking 30 minutes and 8 phone calls for someone to answer, to the multiple stained sheets and beds that are clearly not as advertised - (1 queen, 1 full and 2 twin) - to the missing light bulbs in the rooms and stairwell... I could go on. Again - avoid at all costs."

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

Daniel Z.

[](https://www.expedia.ca/Chicago-Hotels-Comfortable-Condo-In-The-Heart-Of-Bronzeville-By-RedAwning.h103276998.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/107000000/106640000/106630800/106630723/13945995.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106640000/106630800/106630723/3e8a8255.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/107000000/106640000/106630800/106630723/294a1800.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106640000/106630800/106630723/e0b2e5db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Penthouse Condo in Chicago featuring Zero Gravity Massage Chair

Bronzeville

10/10

Exceptional

(23)

"Nice property conveniently located. Easy to get to UChicago campus and downtown. We were in town for UChicago graduation and this place was a good balance for various celebratory activities.Everyone loved the massage chair! Good sized bedrooms and bathrooms. "

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

Tamara J.

[](https://www.expedia.ca/Chicago-Hotels-Penthouse-Condo-In-Chicago-Featuring-Zero-Gravity-Massage-Chair.h106630723.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792556/48f8f2b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792556/4fff30c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792556/2a25922f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792556/c5e0d032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Hyde Park

9.4/10

Exceptional

(3)

"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 $125

CA $302 total

includes taxes & fees

Nov 11 - Nov 12

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90680000/90679300/90679258/61384769.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/91000000/90680000/90679300/90679258/e98f11dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/91000000/90680000/90679300/90679258/2dbb2fcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/91000000/90680000/90679300/90679258/5cbec169.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lux Home in Chicago 7mins Downtown

Bronzeville

9.8/10

Exceptional

(28)

"Larry was super responsive, the property was spotless, the location perfect. Our group of friends loved it. We will be back! "

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

Kyle B.

[](https://www.expedia.ca/Chicago-Hotels-Lux-Home-In-Chicago-7mins-Downtown.h90679258.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104350000/104341900/104341807/6f199fbc.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/105000000/104350000/104341900/104341807/84d1a57d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104350000/104341900/104341807/52ba7bad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/105000000/104350000/104341900/104341807/531c4a08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Condo-Obama & University of Chicago Area

Woodlawn

8.8/10

Excellent

(13)

"It's not often that I'm a complainer. But I have to say, we were appalled by the rental. First and foremost the locks on both front glass doors have been bashed out so anyone can get in. They don't even latch. We never had to open the lockbox, we just walked right in.We had to spend time attempting to get the tops of the windows to close. Ultimately we couldn't force them all closed. It was the biggest problem on friday and Saturday nights when we faced honking cars, fighting tenants, amd very...

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

Michele V.

[](https://www.expedia.ca/Chicago-Hotels-Modern-Condo-Obama-University-Of-Chicago-Area.h104341807.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793062/985b1568.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/117000000/116800000/116793100/116793062/a606f1f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793062/2ebc6ff0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793062/79435de4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bright & Cozy 1BR Near UChicago

Hyde Park

10/10

Exceptional

(2)

"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 $101

CA $251 total

includes taxes & fees

Nov 11 - Nov 12

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

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/120000000/119430000/119426700/119426636/00485267.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/120000000/119430000/119426700/119426636/c4cab1c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119430000/119426700/119426636/4a26d943.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119430000/119426700/119426636/efac9f0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stay, Relax & Explore Chicago

Greater Grand Crossing

9.4/10

Exceptional

(3)

"Our stay was a pleasant surprise. The house was newly renovated and even nicer than the online pictures. Our host Demarcus was quick to respond to our questions and needs. We will stay there again when we go back to visit my granddaughter, a student at UI C "

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

Maria A.

[](https://www.expedia.ca/Chicago-Hotels-Stay.h119426636.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/74000000/73640000/73639200/73639173/c0eeff3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Combined shower/tub, hair dryer, towels, toilet paper](https://images.trvl-media.com/lodging/74000000/73640000/73639200/73639173/76d7780b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, Hulu, streaming services](https://images.trvl-media.com/lodging/74000000/73640000/73639200/73639173/5cf813ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/74000000/73640000/73639200/73639173/f473e16f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Greater Grand Crossing

8.2/10

Very good

(11)

"Came for a concert, enjoyed sight seeing. Apartment was a nice place to stay."

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

APRIL T.

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

![Dining](https://images.trvl-media.com/lodging/95000000/94730000/94721400/94721307/7486dedf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/95000000/94730000/94721400/94721307/40a5fa39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/95000000/94730000/94721400/94721307/w2686h2011x2y3-3f3595f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/95000000/94730000/94721400/94721307/w1320h1248x0y1-c2adfd8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mayors Manor, Zen Garden Oasis, Hot Tub & Sauna in Central Chicago, 8-12 guests

Bridgeport

9.4/10

Exceptional

(20)

"Place was as described and worked perfect for our stay."

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

Timothy D.

[](https://www.expedia.ca/Chicago-Hotels-Elegant-Mayors-Manor-In-Central-Chicago-9-Beds.h94721307.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=2025-11-24&endDate=2025-11-25&regionId=553248635074842823&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Top South Side Hotel Reviews

![Best Western Inn & Suites - Midway Airport](//images.trvl-media.com/lodging/1000000/520000/517500/517495/92ee0c20_y.jpg)

### Best Western Inn & Suites - Midway Airport

10/10 Excellent

"Nice room "

[](https://expedia.ca/Chicago-Hotels-Best-Western-Inn-Suites-Midway-Airport.h517495.Hotel-Information)

![Mccormick Place Guest House](//images.trvl-media.com/lodging/23000000/22680000/22671000/22670906/b6c2dad6_y.jpg)

### Mccormick Place Guest House

10/10 Excellent

"Clean room Quiet Super near bus station Walking distance to a supermarket Could not ask for more !!!!"

[](https://expedia.ca/Chicago-Hotels-Mccormick-Place-Guest-House.h22670906.Hotel-Information)

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

### Jaslin Hotel

10/10 Excellent

"Clean room, walkable to restaurants and Chinatown."

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

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

### SpringHill Suites by Marriott Chicago Chinatown

10/10 Excellent

"Clean room. Great customer service "

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

![Chicago Marriott Midway](//images.trvl-media.com/lodging/1000000/900000/892200/892168/99523df7_y.jpg)

### Chicago Marriott Midway

10/10 Excellent

"The property was excellent the rooms fantastic and the staff were equally wonderful and helpful. "

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

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

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

10/10 Excellent

"Friendly staff, plus clean, big, comfortable room"

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

![Saratoga Motel By Capital O Near Midway Airport Chicago IL](//images.trvl-media.com/lodging/122000000/121180000/121175100/121175039/c14b39fa_y.jpg)

### Saratoga Motel By Capital O Near Midway Airport Chicago IL

10/10 Excellent

"Yes"

[](https://expedia.ca/Chicago-Hotels-Saratoga-Motel-By-Capital-O-Chicago-Midway-IL-US-12.h121175039.Hotel-Information)

![Sophy Hyde Park](//images.trvl-media.com/lodging/23000000/22360000/22355300/22355297/f98af4f7_y.jpg)

### Sophy Hyde Park

10/10 Excellent

"The overall experience!"

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

![Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG](//images.trvl-media.com/lodging/1000000/210000/201300/201281/65c30d17_y.jpg)

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

10/10 Excellent

"Great"

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

## Find out more about South Side

**Everything you need to know about** **South 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 South 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 South Side vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**South Side vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in South 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 South 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 South Side vacation rentals we have selected for you start as low as CA $232 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on South Side rentals**

At Expedia, we put the best South 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 South 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 South 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 South 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

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-   [Québec Vacation Rentals](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

-   [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)
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-   [Aparthotels in South Side](https://expedia.ca/South-Side-Apart-Hotels.d553248635074842823-aaApartHotels.Travel-Guide-Accommodation)

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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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)