Title: Holiday Rentals South Side from £116: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk

[South Side Travel Guide](https://expedia.co.uk/South-Side.dx553248635074842823)[Hotels in South Side](https://expedia.co.uk/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels)[Flights to South Side](https://expedia.co.uk/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights)[Things to do in South Side](https://expedia.co.uk/Things-To-Do-In-South-Side.d553248635074842823.Travel-Guide-Activities)[South Side Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-South-Side.d553248635074842823.Car-Hire-Guide)[South Side Holidays](https://expedia.co.uk/South-Side.d553248635074842823.Holidays-City-Breaks)

![I thought Wood Ducks were the most amazingly colorful and photogenic ducks until I spotted this incredible bird on the lakefront. What a handsome beautiful duck. ](https://images.trvl-media.com/place/829/3b8962fc-94e7-486b-84ab-96e09a77459b.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Richard Remington

# Search Holiday Rentals in South Side

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## Check prices for these dates

In two weeks

[23 Jan - 25 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[6 Mar - 8 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[3 Apr - 5 Apr](https://www.expedia.co.uk/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 four months

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

## Our top choices for South Side holiday rentals

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792489/cf195af6.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)

![2 bedrooms, travel cot, 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.co.uk/Chicago-Hotels-Sleek-Functional-2-Bedroom-Apt.h116792489.Hotel-Information)

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.

£135

includes taxes & fees

11 Jan - 12 Jan

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

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

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792603/73a86148.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.co.uk/Chicago-Hotels-Cozy-Studio-In-Hyde-Park-Walk-To-Lake-University.h116792603.Hotel-Information)

Hyde Park

8.6/10

Excellent

(17)

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

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

Jay M.

£116

includes taxes & fees

11 Jan - 12 Jan

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

![Iron/ironing board, travel cot, 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)

![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)

![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.co.uk/Chicago-Hotels-Cozy-Charm-Studio-Apt-In-Chicago.h117124263.Hotel-Information)

Hyde Park

10/10

Exceptional

(2)

£116

includes taxes & fees

11 Jan - 12 Jan

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

![2 bedrooms, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792556/97f09c42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792556/4af882f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

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

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

Hyde Park

8.4/10

Very good

(5)

"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.

£135

includes taxes & fees

11 Jan - 12 Jan

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

![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/c4d843cc.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)

### Bright 1BR Unit in a Prime Spot

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

Hyde Park

10/10

Exceptional

(1)

"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.

£128

includes taxes & fees

11 Jan - 12 Jan

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

![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)

![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)

### Charming 1BR/1BA Apt in Chicago

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

Hyde Park

10/10

Exceptional

(1)

£128

includes taxes & fees

25 Jan - 26 Jan

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792528/5cd76c20.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)

![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.co.uk/Chicago-Hotels-Bright-South-Hyde-Park-Studio.h116792528.Hotel-Information)

Hyde Park

10/10

Exceptional

(1)

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

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

BiggDas M.

£116

includes taxes & fees

12 Jan - 13 Jan

[](https://www.expedia.co.uk/Chicago-Hotels-Bright-South-Hyde-Park-Studio.h116792528.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)

![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

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

Hyde Park

9.6/10

Exceptional

(5)

"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.

£161

includes taxes & fees

11 Jan - 12 Jan

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

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

![1 bedroom, travel cot, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792510/ec4a8eac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792510/0e90abd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chic Retreat: Cozy 1BR Apartment

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

Hyde Park

9.0/10

Wonderful

(7)

"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.

£128

includes taxes & fees

11 Jan - 12 Jan

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

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792547/6a360b5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792547/f45588c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792547/0d56d480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792547/24a4685e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Contemporary 2BR Apartment in Vibrant Hyde Park

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

Hyde Park

10/10

Exceptional

(1)

"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.

£135

includes taxes & fees

11 Jan - 12 Jan

[](https://www.expedia.co.uk/Chicago-Hotels-Contemporary-2BR-Apartment-In-Vibrant-Hyde-Park.h116792547.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/117000000/116800000/116792500/116792451/52d9308c.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)

### Trendy Studio in Vibrant Area

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

Hyde Park

£116

includes taxes & fees

11 Jan - 12 Jan

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

![Iron/ironing board, travel cot, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792588/382891b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792588/ea85c5ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, travel cot, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792588/71fddc03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792588/ae716d47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Well-Equipped Studio Apt

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

Hyde Park

£116

includes taxes & fees

11 Jan - 12 Jan

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

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

![Iron/ironing board, travel cot, 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)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792613/8070c492.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)

### Trendy Studio Apartment in Chicago

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

Hyde Park

8.0/10

Very good

(3)

"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.

£116

includes taxes & fees

14 Jan - 15 Jan

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

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

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

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

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792582/66917406.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Studio Unit | Chic + Prime Location

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

Hyde Park

10/10

Exceptional

(2)

"Location was just perfect!"

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

Meg D.

£116

includes taxes & fees

11 Jan - 12 Jan

[](https://www.expedia.co.uk/Chicago-Hotels-Studio-Unit-Chic-Prime-Location.h116792582.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/113000000/112540000/112534100/112534056/7a89868d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112540000/112534100/112534056/b09fc9aa.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)

### Modern & Spacious Stay by Northwestern Hospital Bronzeville

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

Bronzeville

10/10

Exceptional

(3)

"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.

£222

includes taxes & fees

11 Jan - 12 Jan

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

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792513/aecee0e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792513/0e60d65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792513/773777dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792513/bc9b4993.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyde Park Haven | 2BR Retreat

[](https://www.expedia.co.uk/Chicago-Hotels-Hyde-Park-Haven-2BR-Retreat.h116792513.Hotel-Information)

Hyde Park

9.0/10

Wonderful

(2)

"Very responsive, nice place "

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

Julian G.

£141

includes taxes & fees

18 Jan - 19 Jan

[](https://www.expedia.co.uk/Chicago-Hotels-Hyde-Park-Haven-2BR-Retreat.h116792513.Hotel-Information)

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793085/29645b8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### Modern 1BR in Historic HydePark

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

Hyde Park

8.4/10

Very good

(15)

"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.

£128

includes taxes & fees

11 Jan - 12 Jan

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

![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)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792567/19a804d5.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.co.uk/Chicago-Hotels-3BR-Complete-Well-Located.h116792567.Hotel-Information)

Hyde Park

7.6/10

Good

(5)

"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.

£161

includes taxes & fees

11 Jan - 12 Jan

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

![1 bedroom, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792640/baa800c8.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)

![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)

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

### Smart Stay in Hyde Park 1BR

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

Hyde Park

£128

includes taxes & fees

14 Jan - 15 Jan

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

![1 bedroom, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792479/e861b994.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792479/0c6cc9cf.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)

### Bright & Modern 1BR in Hyde Park

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

Hyde Park

8.8/10

Excellent

(3)

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

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

Charles S.

£128

includes taxes & fees

14 Jan - 15 Jan

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

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## Top South Side Hotel Reviews

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

### SpringHill Suites by Marriott Chicago Chinatown

10/10 Excellent

"Great staff, easy check in and clean spacious rooms!"

[](https://expedia.co.uk/Chicago-Hotels-SpringHill-Suites-By-Marriott-Chicago-Chinatown.h64624399.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.co.uk/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.co.uk/Chicago-Hotels-Chicago-Marriott-Midway.h892168.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

"Excellent breakfast, comfy bed, BIG room, VERY VERY clean. "

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

"It's always very clean and GREAT location "

[](https://expedia.co.uk/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

"Courteous staff. Clean rooms."

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

![Carlton Inn Midway](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/f9196562_y.jpg)

### Carlton Inn Midway

10/10 Excellent

"It is a good place to stay."

[](https://expedia.co.uk/Chicago-Hotels-Carlton-Inn-Midway.h2949171.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

"Everything was great I really enjoyed!!"

[](https://expedia.co.uk/Chicago-Hotels-Motel-6-Chicago.h115871645.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

"Great hosts"

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

## Find out more about South Side

**Everything you need to know about** **South Side** **holiday rentals**

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the South Side holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/Villas)... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect South Side holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

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

Whenever you want to travel, a warm welcome awaits you in South Side. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A South Side holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of South Side holiday rentals we have selected for you start as low as £116 per night. Entering your travel dates in the search wizard you might find even better deals!

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

At Expedia, we put the best South Side holiday 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 holiday.

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

- Trending destinations on Expedia.co.uk
- All accommodation types in South Side

### Trending destinations on Expedia.co.uk

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- [York Holiday Rentals ](https://www.expedia.co.uk/York-Holiday-Rentals.d5489.Travel-Guide-HolidayRentals)
- [Blackpool Holiday Rentals ](https://www.expedia.co.uk/Blackpool-Holiday-Rentals.d619.Travel-Guide-HolidayRentals)
- [Isle of Wight Holiday Rentals ](https://www.expedia.com/Destinations-In-Isle-Of-Wight.d6046218.Vacation-Rental-Destinations)
- [Scarborough Holiday Rentals ](https://www.expedia.co.uk/Scarborough-Holiday-Rentals.d5680.Travel-Guide-HolidayRentals)
- [Edinburgh Holiday Rentals ](https://www.expedia.co.uk/Edinburgh-Holiday-Rentals.d6069845.Travel-Guide-HolidayRentals)
- [Bath Holiday Rentals ](https://www.expedia.co.uk/Bath-Holiday-Rentals.d6084496.Travel-Guide-HolidayRentals)
- [Bournemouth Holiday Rentals ](https://www.expedia.co.uk/Bournemouth-Holiday-Rentals.d654.Travel-Guide-HolidayRentals)
- [England Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-England.d11218.Holiday-Rental-Destinations)
- [Scotland Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Scotland.d11219.Holiday-Rental-Destinations)
- [Cornwall Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Cornwall.d6046193.Holiday-Rental-Destinations)
- [Wales Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Wales.d11220.Holiday-Rental-Destinations)
- [Northern Ireland Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Northern-Ireland.d11221.Holiday-Rental-Destinations)

- [Apartments in South Side ](https://expedia.co.uk/South-Side-Apartments.d553248635074842823-aaApartments.Travel-Guide-Accommodation)
- [Holiday Homes in South Side ](https://expedia.co.uk/South-Side-Private-Holiday-Homes.d553248635074842823-aaPrivateHolidayHomes.Travel-Guide-Accommodation)
- [Condo Rentals in South Side ](https://expedia.co.uk/South-Side-Condos.d553248635074842823-aaCondos.Travel-Guide-Accommodation)
- [Motels in South Side ](https://expedia.co.uk/South-Side-Motels.d553248635074842823-aaMotels.Travel-Guide-Accommodation)
- [Guest Houses in South Side ](https://expedia.co.uk/South-Side-Guest-Houses.d553248635074842823-aaGuestHouses.Travel-Guide-Accommodation)
- [Serviced Apartments in South Side ](https://expedia.co.uk/South-Side-Apart-Hotels.d553248635074842823-aaApartHotels.Travel-Guide-Accommodation)

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