Title: South Side Vacation Rentals from CA $217: 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, IL featuring interior views and an airport as well as a couple](https://images.trvl-media.com/place/5719117/eadab43c-a88e-4198-bdcd-703715c2ebbd.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by by Midway Intl Airport

# South Side Vacation Rentals

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## Check prices for these dates

In two weeks

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Vacation Rentals in South Side

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107620000/107610900/107610850/11a06bac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107620000/107610900/107610850/25a43c03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107620000/107610900/107610850/9f88264e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, stereo](https://images.trvl-media.com/lodging/108000000/107620000/107610900/107610850/d0556cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1-bedroom condo next to Chicago Midway International Airport

Garfield Ridge

10/10

Exceptional

(12)

"Perfect location, modern condo and clean. I would highly recommend "

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

Christopher and Emily L.

[](https://www.expedia.ca/Chicago-Hotels-1st-Floor-1-Bedroom-Condo-Close-To-Chicago-Midway-International-Airport.h107610850.Hotel-Information)

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117130000/117124300/117124263/f3e50bcf.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)

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117130000/117124300/117124263/32c9cb69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Charm Studio Apt in Chicago

Hyde Park

10/10

Exceptional

(1)

CA $84

CA $217 total

includes taxes & fees

Dec 3 - Dec 4

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

![Interior](https://images.trvl-media.com/lodging/104000000/103950000/103943300/103943206/853ce9f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/104000000/103950000/103943300/103943206/e32db205.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103950000/103943300/103943206/3f4a650f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/104000000/103950000/103943300/103943206/aa345e6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### A Home Away From Home!

Calumet Heights

9.6/10

Exceptional

(13)

"Great place to stay. Host responded quickly to questions. Location was good and neighbor was quite. "

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

Marchand J.

[](https://www.expedia.ca/Chicago-Hotels-A-Home-Away-From-Home.h103943206.Hotel-Information)

![Iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792603/986d35ab.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/117000000/116800000/116792700/116792603/12f4bdd5.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

8.6/10

Excellent

(14)

"This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. "

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

Nancy

CA $84

CA $217 total

includes taxes & fees

Dec 3 - Dec 4

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70890000/70886100/70886010/03d3c9c4.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)

![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)

![Game room](https://images.trvl-media.com/lodging/71000000/70890000/70886100/70886010/w828h549x0y0-b2df28f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### LakeHouse

South Shore

9.4/10

Exceptional

(24)

"Everything was perfect with the property and the host even came to help right away when we had one issue with the lights."

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

Isaiah P.

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

![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)

![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)

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

Bronzeville

10/10

Exceptional

(25)

"Perfect for what we needed"

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

Richard G.

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

![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/cc47c33f.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

(10)

"Clean room and convenient location! "

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

Gabriela

CA $84

CA $217 total

includes taxes & fees

Dec 7 - Dec 8

[](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)

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793085/dae3dcce.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)

### Modern 1BR in Historic HydePark

Hyde Park

8.2/10

Very good

(12)

"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 $77

CA $222 total

includes taxes & fees

Dec 3 - Dec 4

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

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792497/49b10dc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792497/80d49650.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792497/270caa93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792497/0327bf8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Furnished 3BR Apt w/ Laundry

Hyde Park

9.6/10

Exceptional

(4)

"Apartment and neighborhood were beautiful. We really enjoyed our stay and would book the same place again!"

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

Kristin W.

CA $82

CA $271 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Chicago-Hotels-Furnished-3BR-Apt-W-Laundry.h116792497.Hotel-Information)

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

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

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

![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 $339

CA $543 total

includes taxes & fees

Dec 3 - Dec 4

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

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

![Interior](https://images.trvl-media.com/lodging/114000000/113100000/113092000/113091937/dca9efff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

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

Auburn Gresham

8.8/10

Excellent

(6)

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

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

Jessica M.

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

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792510/a4c1202d.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)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792510/0e90abd7.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)

### Chic Retreat: Cozy 1BR Apartment

Hyde Park

9.0/10

Wonderful

(6)

"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 $77

CA $222 total

includes taxes & fees

Dec 2 - Dec 3

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

![Dining](https://images.trvl-media.com/lodging/111000000/110370000/110363000/110362923/c61a0963.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/111000000/110370000/110363000/110362923/cb1acba6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110370000/110363000/110362923/eab820b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/111000000/110370000/110363000/110362923/69307536.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming house in amazing Chicago with WiFi and AC. Close to many restaurants.

Avalon Park

9.4/10

Exceptional

(6)

"The home was set up perfectly for our family. Everyone had a comfy bedroom and there were multiple family living spaces to spread out. We enjoyed our stay. Cozy home!"

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

Kristi T.

[](https://www.expedia.ca/Chicago-Hotels-Charming-House-In-Amazing-Chicago-With-WiFi-And-AC-Close-To-Many-Restaurants.h110362923.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)

![Interior](https://images.trvl-media.com/lodging/104000000/103770000/103763600/103763530/085547e8.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)

"We had a good time here!"

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

Shane C.

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

![Interior](https://images.trvl-media.com/lodging/91000000/90680000/90679300/90679258/f359b69d.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)

### 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)

![Interior](https://images.trvl-media.com/lodging/117000000/116240000/116238300/116238230/c4821ce0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116240000/116238300/116238230/w1080h1440x0y16-cbb4ff2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/117000000/116240000/116238300/116238230/74d36cff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116240000/116238300/116238230/w1080h1440x0y8-2e6765a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Relax & Unwind in This Comfortable 3BR Unit

Calumet Park

10/10

Exceptional

(5)

"Lakeia was very accommodating throughout our stay."

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

Timothy K.

CA $186

CA $441 total

includes taxes & fees

Dec 8 - Dec 9

[](https://www.expedia.ca/Chicago-Hotels-Relax-Unwind-In-This-Comfortable-3BR-Unit.h116238230.Hotel-Information)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/103000000/102740000/102735800/102735782/079c5ec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, video games, stereo](https://images.trvl-media.com/lodging/103000000/102740000/102735800/102735782/402f1ed6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/103000000/102740000/102735800/102735782/7f7f5bc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102740000/102735800/102735782/b0e082d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stay near family or close to downtown, this loft in Beverly has it all!

Beverly

9.8/10

Exceptional

(11)

"We really enjoyed our time in Chicago for our family reunion. The price was spot on as the hotels cost in Chicago are super expensive. The location was very safe, great area for restaurants and shopping. We will definitely stay here again. Also, great host! "

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

Theresa S.

[](https://www.expedia.ca/Chicago-Hotels-Stay-Near-Family-Or-Close-To-Downtown.h102735782.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

8.6/10

Excellent

(14)

"I thought this place was so cute, loved the outset deck! Was spacious and the host was very nice and helpful when needed! Would stay again for sure! "

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

Jaime C.

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

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792489/3ded30c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792489/7e43465a.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)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792489/dd9a1f6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sleek & Functional 2-Bedroom Apt

Hyde Park

9.6/10

Exceptional

(4)

"Nice place for a girls trip weekend. "

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

Madonna A.

CA $87

CA $255 total

includes taxes & fees

Dec 2 - Dec 3

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102660000/102659900/102659809/3b40be43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/103000000/102660000/102659900/102659809/ecd5dba3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102660000/102659900/102659809/587528e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/103000000/102660000/102659900/102659809/06ae3dda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gorgeous historic mansion on UChicago campus. Renovation with original detail.

Hyde Park

10/10

Exceptional

(15)

"The check-in process was effortless and the kitchen was well appointed."

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

Theophlius K.

[](https://www.expedia.ca/Chicago-Hotels-Gorgeous-Historic-Mansion-On-UChicago-Campus-Renovation-With-Original-Detail.h102659809.Hotel-Information)

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

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## Find vacation rentals that suit your style

Cabins

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Cottages

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Aparthotels

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Apartments

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Villas

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Condos

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Private vacation homes

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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=2026-03-01&d1=2026-03-01&endDate=2026-03-04&d2=2026-03-04&lodging=RESIDENCE)

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## Top South Side Hotel Reviews

![Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG](https://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

"The need to stay in Chicago overnight was unplanned so finding the room clean and looking comfortable right away made my stress level come down"

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

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

### Sophy Hyde Park

10/10 Excellent

"Very nice room and amenities. We enjoy the atmosphere in the lobby!!"

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

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

### Chicago Marriott Midway

10/10 Excellent

"Very convenient and clean and friendly! "

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

![Motel 6 - Chicago, IL](https://images.trvl-media.com/lodging/116000000/115880000/115871700/115871645/55e03c95_y.jpg)

### Motel 6 - Chicago, IL

10/10 Excellent

"Grest"

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

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

### Jaslin Hotel

10/10 Excellent

"Excellent- we were able to check out late for a small fee"

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

"As always fabulous experience. Great customer service."

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

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

### Best Western Inn & Suites - Midway Airport

10/10 Excellent

"Hotel and room was very clean and the desk clerk was courteous "

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

![Saratoga Motel By Capital O Near Midway Airport Chicago IL](https://images.trvl-media.com/lodging/122000000/121180000/121175100/121175039/w3451h2304x0y0-39d39828_y.jpg)

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

10/10 Excellent

"Room was spotless "

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

![Best Motel By OYO Chicago I-90](https://images.trvl-media.com/lodging/14000000/13280000/13279200/13279118/19cdbb10_y.jpg)

### Best Motel By OYO Chicago I-90

8/10 Good

"Clean room "

[](https://expedia.ca/Chicago-Hotels-Best-Motel-By-OYO-Chicago-I-90.h13279118.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.  

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-   [Apartments in South Side](https://expedia.ca/South-Side-Apartments.d553248635074842823-aaApartments.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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)