Title: South Side Vacation Rentals from CA $210: 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

[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 two months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-05-08&endDate=2026-05-10&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](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792603/986d35ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792603/73a86148.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

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

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

Hyde Park

8.6/10

Excellent

(17 reviews)

"The room was clean, amenities worked, and coffee was provided!"

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

Jay M.

CA $79

CA $210 total

includes taxes & fees

Jan 18 - Jan 19

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

![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)

![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/117000000/116800000/116793100/116793062/56a939d5.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 $88

CA $234 total

includes taxes & fees

Jan 18 - Jan 19

[](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)

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

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792582/66917406.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)

### Studio Unit | Chic + Prime Location

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

Hyde Park

10/10

Exceptional

(2 reviews)

"Location was just perfect!"

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

Meg D.

CA $79

CA $210 total

includes taxes & fees

Jan 19 - Jan 20

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

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792510/9bbc072b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792510/85599456.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)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792510/fff7851c.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 $88

CA $234 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Chicago-Hotels-Chic-Retreat-Cozy-1BR-Apartment.h116792510.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/c4d843cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792457/78b2e98e.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)

### 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 $88

CA $234 total

includes taxes & fees

Jan 25 - Jan 26

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

![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)

![Interior](https://images.trvl-media.com/lodging/118000000/117130000/117124300/117124263/8074f855.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)

### 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

(3 reviews)

"Everying was great."

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

Ryan D.

CA $79

CA $210 total

includes taxes & fees

Jan 18 - Jan 19

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

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793085/cbfefe40.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)

![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/117000000/116800000/116793100/116793085/28211659.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern 1BR in Historic HydePark

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

Hyde Park

8.4/10

Very good

(15 reviews)

"The location couldn't be beat. The beds were super comfortable and the room was perfect for my husband and I. We'll definitely stay here again!"

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

Lisa O.

CA $88

CA $234 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Chicago-Hotels-Modern-1BR-In-Historic-HydePark.h116793085.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/117000000/116800000/116793100/116793049/725729b5.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)

![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)

### 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 $79

CA $224 total

includes taxes & fees

Jan 18 - Jan 19

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

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792489/7d0f8c07.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)

![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)

### 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 $81

CA $247 total

includes taxes & fees

Jan 20 - Jan 21

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

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792541/900036cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792541/d45cd4d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792541/279f144b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792541/ab2a4e99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Compact Studio for a Relaxed Stay

[](https://www.expedia.ca/Chicago-Hotels-Compact-Studio-For-A-Relaxed-Stay.h116792541.Hotel-Information)

Hyde Park

8.0/10

Very good

(1 review)

CA $79

CA $210 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Chicago-Hotels-Compact-Studio-For-A-Relaxed-Stay.h116792541.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792479/ae8fd0e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792479/50cc7258.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/117000000/116800000/116792500/116792479/e861b994.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792479/caa8e7ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bright & Modern 1BR in Hyde Park

[](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 $88

CA $234 total

includes taxes & fees

Jan 18 - Jan 19

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

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792556/ecfbc13a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792556/89c64f25.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)

### 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

8.4/10

Very good

(5 reviews)

"Host was responsive to my questions. Apartment is located in a great area of Hyde Park. "

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

Lind A.

CA $81

CA $248 total

includes taxes & fees

Jan 22 - Jan 23

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

![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)

![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)

![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 $79

CA $210 total

includes taxes & fees

Jan 18 - Jan 19

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

![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)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792497/02fd94e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792497/83ec6dc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Furnished 3BR Apt w/ Laundry

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

Hyde Park

9.6/10

Exceptional

(5 reviews)

"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 $104

CA $304 total

includes taxes & fees

Jan 20 - Jan 21

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

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792547/0ce816d2.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/117000000/116800000/116792600/116792547/2f0faaa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792547/b29ceff6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792547/2b69062f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Contemporary 2BR Apartment in Vibrant Hyde Park

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

Hyde Park

10/10

Exceptional

(1 review)

"We stayed in this comfortable, quiet apartment for four weeks when my husband was undergoing radiation treatments for cancer at the University of Chicago Medical Center. It was just what we needed. The location—a block from Lake Michigan with its endless miles of parks and green spaces—was spectacular, and we spent long hours walking our dogs and biking along the lake on the beautifully landscaped walking and biking trails. The apartment itself is well appointed, clean, and blessedly quiet...

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

Heidi H.

CA $81

CA $247 total

includes taxes & fees

Jan 20 - Jan 21

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

![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)

![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)

### 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 $122

CA $491 total

includes taxes & fees

Jan 19 - Jan 20

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

![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792472/18432d6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792472/c7464dee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792472/aed0e4b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, stovetop, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792472/b579fe64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 3BR with Contemporary Vibe

[](https://www.expedia.ca/Chicago-Hotels-Cozy-3BR-With-Contemporary-Vibe.h116792472.Hotel-Information)

Hyde Park

7.0/10

Good

(2 reviews)

"IT was clean but the neighbourhood was A little sketchy"

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

cara m.

CA $104

CA $300 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Chicago-Hotels-Cozy-3BR-With-Contemporary-Vibe.h116792472.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792567/c283a70a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792567/9f09ad08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792567/d2647f3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792567/dfaa443f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 3BR | Complete & Well-Located

[](https://www.expedia.ca/Chicago-Hotels-3BR-Complete-Well-Located.h116792567.Hotel-Information)

Hyde Park

7.6/10

Good

(5 reviews)

"Very nice place! Not many kitchen amenities available as there was no way to heat up something in the oven with no baking sheet or foil. Getting into the apartment was not very easy as we had to call a number to be remotely let in every time we wanted to use the front door."

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

Teri D.

CA $104

CA $304 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Chicago-Hotels-3BR-Complete-Well-Located.h116792567.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/113000000/112540000/112534100/112534056/w1024h674x0y4-c8d01466.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/113000000/112540000/112534100/112534056/59cc12db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/113000000/112540000/112534100/112534056/7608b471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/113000000/112540000/112534100/112534056/7a89868d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern & Spacious Stay by Northwestern Hospital Bronzeville

[](https://www.expedia.ca/Chicago-Hotels-Modern-Spacious-Stay-In-Historic-Bronzeville.h112534056.Hotel-Information)

Bronzeville

10/10

Exceptional

(3 reviews)

"What a great place to stay! Interior of the unit was very nice and modern. Amenities were great. We felt safe and secure the entire time. Our host was in constant communication to make sure our needs were met. We would definitely recommend this stay!"

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

Matt D.

CA $75

CA $423 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Chicago-Hotels-Modern-Spacious-Stay-In-Historic-Bronzeville.h112534056.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792528/dd9e0f78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792528/3ed7ce53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792528/1ee73694.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792528/e8067ee8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bright South Hyde Park Studio

[](https://www.expedia.ca/Chicago-Hotels-Bright-South-Hyde-Park-Studio.h116792528.Hotel-Information)

Hyde Park

10/10

Exceptional

(1 review)

"Comfortable space in a nice neighborhood. I highly recommend."

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

BiggDas M.

CA $79

CA $210 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Chicago-Hotels-Bright-South-Hyde-Park-Studio.h116792528.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=2026-01-31&endDate=2026-02-01&regionId=553248635074842823&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

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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=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&lodging=APART_HOTEL)

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=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&lodging=APARTMENT)

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=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&lodging=VILLA)

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=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&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=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&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=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&lodging=RESIDENCE)

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## Top South Side Hotel Reviews

![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

"Very clean and Comfortable "

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

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

### Sophy Hyde Park

10/10 Excellent

"The view and room was awesome."

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

"Very easy, friendly staff"

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

![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

"Great location. Easy access and great facility"

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

"Room was clean staff was nice elevator is scary though."

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

![Chinatown Hotel Chicago](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/85295fe8_y.jpg)

### Chinatown Hotel Chicago

10/10 Excellent

"Get what you pay for! "

[](https://expedia.ca/Chicago-Hotels-Chinatown-Hotel-Chicago.h1118357.Hotel-Information)

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

### Jaslin Hotel

10/10 Excellent

"Have to pay for parking "

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

![Holiday Inn Chicago – Midway Airport S by IHG](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/w3836h2161x5y0-7f85e9e1_y.jpg)

### Holiday Inn Chicago – Midway Airport S by IHG

10/10 Excellent

"Close to arpt"

[](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Mall-Area-Mdw-Arpt-S.h2190.Hotel-Information)

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

### Chicago Marriott Midway

10/10 Excellent

"Spent a night! Wish I could have stayed longer. The space was clean and beautifully designed, and the hotel staff were extremely accommodating to my needs. Wish I had gotten to enjoy the menu items, but I had to get back to the airport. The shuttle was also great; it came every 20 minutes, and I loved saving money on ride-sharing back to the airport in the morning. Overall great! "

[](https://expedia.ca/Chicago-Hotels-Chicago-Marriott-Midway.h892168.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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- [YVR to PHL flights](https://expedia.ca/lp/flights/yvr/phl/vancouver-to-philadelphia)
- [YYZ to ROM flights](https://expedia.ca/lp/flights/yyz/rom/toronto-to-rome)
- [Cheap Flights from Norman Rogers Airport](https://expedia.ca/lp/airports/ygk/flights-from-norman-rogers-airport)
- [YYZ to BLC flights](https://expedia.ca/lp/flights/yyz/blc/toronto-to-bali)

Cars

- [Enterprise Car Rentals In Toronto](https://expedia.ca/Enterprise-Car-Rentals-In-Toronto.d178314-c15.Car-Rental-Guide-Suppliers)

Packages

- [TELUS Spark](https://expedia.ca/TELUS-Spark-Downtown-Calgary.d6072191.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)
- [Willis Tower](https://expedia.ca/Willis-Tower-Downtown-Chicago.d6064069.Vacation-Attraction)
- [Griffin Museum of Science and Industry](https://expedia.ca/Griffin-Museum-Of-Science-And-Industry-Hyde-Park.d6064043.Vacation-Attraction)
- [Grant Park](https://expedia.ca/Grant-Park-Downtown-Chicago.d507389.Vacation-Attraction)

General

- [Flight Deals & Seat Sales](https://expedia.ca/flight-deals)

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