Title: South Side Vacation Rentals from $181: Search Short-Term Rentals | Expedia.com

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

[Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=553248635074842823&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 15 - May 17](https://www.expedia.com/Hotel-Search?regionId=553248635074842823&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 12 - Jun 14](https://www.expedia.com/Hotel-Search?regionId=553248635074842823&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 10 - Jul 12](https://www.expedia.com/Hotel-Search?regionId=553248635074842823&startDate=2026-07-10&endDate=2026-07-12&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

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

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

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

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

### Apartment in Brighton Park

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

10/10

Exceptional

(1 review)

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

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

Fabian H.

$230 nightly

$258 total

Mar 24 - Mar 25

Total with taxes and fees

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117130000/117124300/117124263/431d74e0.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)

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

### Apartment in Hyde Park

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

10/10

Exceptional

(4 reviews)

"Everying was great."

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

Ryan D.

$162 nightly

$181 total

Mar 22 - Mar 23

Total with taxes and fees

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

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

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

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

![Exterior detail](https://images.trvl-media.com/lodging/97000000/96480000/96479300/96479287/3bda02c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Brighton Park

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

9.4/10

Exceptional

(9 reviews)

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

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

Jessica H.

$233 nightly

$261 total

Mar 23 - Mar 24

Total with taxes and fees

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

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

![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)

### Apartment in Hyde Park

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

10/10

Exceptional

(3 reviews)

"Location was just perfect!"

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

Meg D.

$162 nightly

$181 total

Mar 22 - Mar 23

Total with taxes and fees

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

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

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

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

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

### Apartment in Hyde Park

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

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.

$197 nightly

$218 total

Mar 22 - Mar 23

Total with taxes and fees

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

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

![Shower](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793083/6c56b652.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

### Apartment in Hyde Park

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

8.8/10

Excellent

(15 reviews)

"Clean room and convenient location! "

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

Gabriela

$162 nightly

$181 total

Mar 22 - Mar 23

Total with taxes and fees

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

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

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

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793062/56a939d5.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)

### Apartment in Hyde Park

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

9.6/10

Exceptional

(4 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.

$178 nightly

$198 total

Mar 22 - Mar 23

Total with taxes and fees

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

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

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

![Coffee and/or coffee maker](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792588/d747c438.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### Apartment in Hyde Park

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

$162 nightly

$181 total

Mar 23 - Mar 24

Total with taxes and fees

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

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

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

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792547/067c51c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### Apartment in Hyde Park

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

10/10

Exceptional

(2 reviews)

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

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

Allison K.

$205 nightly

$227 total

Apr 1 - Apr 2

Total with taxes and fees

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

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

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

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792479/b67152a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### Apartment in Hyde Park

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

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.

$178 nightly

$198 total

Mar 22 - Mar 23

Total with taxes and fees

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

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

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

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

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

### Apartment in Hyde Park

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

$162 nightly

$181 total

Mar 22 - Mar 23

Total with taxes and fees

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

![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)

![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)

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

### Apartment in Hyde Park

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

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.

$178 nightly

$198 total

Mar 29 - Mar 30

Total with taxes and fees

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

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

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

![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792510/59ac3299.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### Apartment in Hyde Park

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

9.0/10

Wonderful

(7 reviews)

"It was a cozy place and clean. Sleeping was comfy minus outside noise at night can be a bit much. "

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

Brandie O.

$178 nightly

$198 total

Mar 22 - Mar 23

Total with taxes and fees

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

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793077/52047153.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793077/f72466f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793077/c993e105.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793077/6ec56159.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Hyde Park

[](https://www.expedia.com/Chicago-Hotels-Charming-1BR1BA-Apt-In-Chicago.h116793077.Hotel-Information)

10/10

Exceptional

(1 review)

$178 nightly

$198 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Charming-1BR1BA-Apt-In-Chicago.h116793077.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)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792613/0b1f4ad5.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)

### Apartment in Hyde Park

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

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.

$162 nightly

$181 total

Mar 22 - Mar 23

Total with taxes and fees

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

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

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

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

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

### Vacation Home in South Shore

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

$473 nightly

$529 total

Mar 30 - Mar 31

Total with taxes and fees

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

![Iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793055/dfd5dc7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793055/5d76f857.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793055/15ade6ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793055/c82f2acd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Kenwood

[](https://www.expedia.com/Chicago-Hotels-Stylish-HydePark-Studio-Retreat.h116793055.Hotel-Information)

$162 nightly

$181 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Stylish-HydePark-Studio-Retreat.h116793055.Hotel-Information)

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

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

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

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792640/152d977f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Hyde Park

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

$179 nightly

$199 total

Mar 26 - Mar 27

Total with taxes and fees

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

![TV, offices](https://images.trvl-media.com/lodging/117000000/116910000/116903600/116903580/ccaf1964.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/117000000/116910000/116903600/116903580/f9e66b80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116910000/116903600/116903580/aeb7b559.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116910000/116903600/116903580/a031904d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Hyde Park

[](https://www.expedia.com/Chicago-Hotels-Perfect-1BR-Spot-Near-Attractions.h116903580.Hotel-Information)

7.8/10

Good

(6 reviews)

"We were there visiting our daughter at Hyde Park. The location was great, near restaurants and shopping. The space was comfortable and clean. "

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

Alex & Minerva B.

$178 nightly

$198 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Perfect-1BR-Spot-Near-Attractions.h116903580.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792607/a850690d.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/117000000/116800000/116792700/116792607/8332703f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792607/dc01c189.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792607/8f3aedc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Hyde Park

[](https://www.expedia.com/Chicago-Hotels-Prime-Spot.h116792607.Hotel-Information)

6.4/10

(9 reviews)

"The host was easy to communicate with and responded quickly with my questions.Rooms/bathroom/kitchen were clean and had everything we needed."

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

Sheri B.

$178 nightly

$198 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Prime-Spot.h116792607.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.com/Hotel-Search?startDate=2026-04-03&endDate=2026-04-04&regionId=553248635074842823&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cottages

[](https://www.expedia.com/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-06-18&d1=2026-06-18&endDate=2026-06-21&d2=2026-06-21&lodging=COTTAGE)

Private vacation homes

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Condos

[](https://www.expedia.com/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-06-18&d1=2026-06-18&endDate=2026-06-21&d2=2026-06-21&lodging=CONDO)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-06-18&d1=2026-06-18&endDate=2026-06-21&d2=2026-06-21&lodging=APARTMENT)

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-06-18&d1=2026-06-18&endDate=2026-06-21&d2=2026-06-21&lodging=APART_HOTEL)

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## Top South Side Hotel Reviews

![Villa Dubois Guest House](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/d0c2eca1_y.jpg)

### Villa Dubois Guest House

6/10 Okay

"Quaint and quiet for solo travelers. A pretty cozy stay but be very cautious of the refundable deposit. They’re not on it like your average hotel/airbnb so you will have to remind them via email. Their phone number isn’t the greatest, as it is hard to communicate to the staff, they don’t have a regular set of hours by the phone. Kitchen wasn’t used for my stay but it looked neat and clean, perfect for those who intend on staying longer. "

[](https://expedia.com/Chicago-Hotels-Villa-Dubois-Guest-House.h35542249.Hotel-Information)

![Chicago Lake Shore Hotel](https://images.trvl-media.com/lodging/1000000/10000/7400/7341/5dc5b9fc_y.jpg)

### Chicago Lake Shore Hotel

4/10 Poor

"When it was check in time the first desk reception was rude. Seemed like didn’t know what to do and didn’t know the policy "

[](https://expedia.com/Chicago-Hotels-Chicago-Lake-Shore-Hotel.h7341.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

"Very enjoyable stay. Great little restaurants nearby."

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

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

### Motel 6 - Chicago, IL

6/10 Okay

"Lady at front desk always have an attitude"

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

![Carlton Inn Midway](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/efb1181a_y.jpg)

### Carlton Inn Midway

2/10 Terrible

"Room is dirty, bad cleaning. Gave us a single bedroom as we ordered double bedroom online, and they refused to give any refund. Suck motel overall."

[](https://expedia.com/Chicago-Hotels-Carlton-Inn-Midway.h2949171.Hotel-Information)

![Holiday Inn Chicago – Midway Airport S by IHG](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/d5acb403_y.jpg)

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

10/10 Excellent

"Fast, friendly, outstanding service"

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

![Saratoga Motel By Capital O Near Midway Airport Chicago IL](https://images.trvl-media.com/lodging/122000000/121180000/121175100/121175039/w3456h2300x0y0-6e038619_y.jpg)

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

6/10 Okay

"N/A"

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

![Stylish Apartment near Chicago Downtown](https://images.trvl-media.com/lodging/120000000/119980000/119973600/119973593/58a3b7eb_y.jpg)

### Stylish Apartment near Chicago Downtown

10/10 Excellent

"Perfect place , nice location, the only thing needed is a mop or a broom Other than that great home"

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

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

### Chicago Marriott Midway

10/10 Excellent

"Great"

[](https://expedia.com/Chicago-Hotels-Chicago-Marriott-Midway.h892168.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, apartments, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit South Side in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $181 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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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- [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
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- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

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

### Expedia's Latest Trends

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