South Side Holiday Rentals

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Our top choices for South Side holiday rentals

Cozy Studio in Hyde Park-Walk to Lake & University

Cozy Studio in Hyde Park-Walk to Lake & University
Hyde Park
8.6 out of 10, Excellent, (17 reviews)
"The room was clean, amenities worked, and coffee was provided!"
United States
Jay M.
The price is AU$220
includes taxes & fees
10 Feb - 11 Feb
Cozy Studio in Hyde Park-Walk to Lake & University

Cozy Charm Studio Apt in Chicago

Cozy Charm Studio Apt in Chicago
Hyde Park
10.0 out of 10, Exceptional, (3 reviews)
"Everying was great."
United States
Ryan D.
The price is AU$220
includes taxes & fees
10 Feb - 11 Feb
Cozy Charm Studio Apt in Chicago

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Brighton Park
8.6 out of 10, Excellent, (21 reviews)
"Clean and nice. My son loved the arcade game. Would stay again "
United States
Nichole S.
The price is AU$283
includes taxes & fees
10 Feb - 11 Feb
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

Studio Unit | Chic + Prime Location

Studio Unit | Chic + Prime Location
Hyde Park
10.0 out of 10, Exceptional, (2 reviews)
"Location was just perfect!"
United States
Meg D.
The price is AU$220
includes taxes & fees
10 Feb - 11 Feb
Studio Unit | Chic + Prime Location

Sleek & Functional 2-Bedroom Apt

Sleek & Functional 2-Bedroom Apt
Hyde Park
9.6 out of 10, Exceptional, (4 reviews)
"Nice place for a girls trip weekend. "
United States
Madonna A.
The price is AU$281
includes taxes & fees
10 Feb - 11 Feb
Sleek & Functional 2-Bedroom Apt

Near Lake and Museum • Modern • Game Area

Near Lake and Museum • Modern • Game Area
South Shore
The price is AU$629
includes taxes & fees
10 Feb - 11 Feb
Near Lake and Museum • Modern • Game Area

Furnished 3BR Apt w/ Laundry

Furnished 3BR Apt w/ Laundry
Hyde Park
9.8 out of 10, Exceptional, (6 reviews)
"Apartment and neighborhood were beautiful. We really enjoyed our stay and would book the same place again!"
United States
Kristin W.
The price is AU$308
includes taxes & fees
10 Feb - 11 Feb
Furnished 3BR Apt w/ Laundry

Bright 1BR Unit in a Prime Spot

Bright 1BR Unit in a Prime Spot
Hyde Park
10.0 out of 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
christine m.
The price is AU$253
includes taxes & fees
10 Feb - 11 Feb
Bright 1BR Unit in a Prime Spot

Bright South Hyde Park Studio

Bright South Hyde Park Studio
Hyde Park
10.0 out of 10, Exceptional, (1 review)
"Comfortable space in a nice neighborhood. I highly recommend."
United States
BiggDas M.
The price is AU$220
includes taxes & fees
12 Feb - 13 Feb
Bright South Hyde Park Studio

Private 1BR Haven in a Prime Area

Private 1BR Haven in a Prime Area
Hyde Park
9.0 out of 10, Wonderful, (7 reviews)
"Our stay was very nice, with simple checkin / check out, and excellent communication by our host. "
United States
Tom B.
The price is AU$253
includes taxes & fees
10 Feb - 11 Feb
Private 1BR Haven in a Prime Area

Charming 1BR/1BA Apt in Chicago

Charming 1BR/1BA Apt in Chicago
Hyde Park
10.0 out of 10, Exceptional, (1 review)
The price is AU$253
includes taxes & fees
15 Feb - 16 Feb
Charming 1BR/1BA Apt in Chicago

Explore Hyde Park: 2BR Apartment on Blackstone Ave

Explore Hyde Park: 2BR Apartment on Blackstone Ave
Hyde Park
7.4 out of 10, Good, (6 reviews)
"All the necessities with no personal touches. Keys from lockbox to open second door were not needed as the second door is always open. Impeccable communication with host. Great location, close to restaurants and train to Millennium Station. Coffee service was excellent, just be sure to find extra pouches in cabinet. Bathtub faucet could not be turned far enough to prevent leaking. TV remote not great and I couldn’t get CNN or MSNBC. I’d stay here again. "
United States
lost whale press
The price is AU$281
includes taxes & fees
10 Feb - 11 Feb
Explore Hyde Park: 2BR Apartment on Blackstone Ave

Bright & Cozy 1BR Near UChicago

Bright & Cozy 1BR Near UChicago
Hyde Park
9.4 out of 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
Alan F.
The price is AU$253
includes taxes & fees
10 Feb - 11 Feb
Bright & Cozy 1BR Near UChicago

Sunlit & Chic 2BR Retreat

Sunlit & Chic 2BR Retreat
Hyde Park
10.0 out of 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
Heidi H.
The price is AU$281
includes taxes & fees
10 Feb - 11 Feb
Sunlit & Chic 2BR Retreat

Compact Studio for a Relaxed Stay

Compact Studio for a Relaxed Stay
Hyde Park
8.0 out of 10, Very good, (1 review)
The price is AU$220
includes taxes & fees
16 Feb - 17 Feb
Compact Studio for a Relaxed Stay

Hyde Park Haven | 2BR Retreat

Hyde Park Haven | 2BR Retreat
Hyde Park
9.0 out of 10, Wonderful, (2 reviews)
"Very responsive, nice place "
United States
Julian G.
The price is AU$281
includes taxes & fees
10 Feb - 11 Feb
Hyde Park Haven | 2BR Retreat

Modern 1BR in Historic HydePark

Modern 1BR in Historic HydePark
Hyde Park
8.0 out of 10, Very good, (16 reviews)
"Great location, attentive host. No frills but clean, and the beds were comfortable. "
United States
Michelle R.
The price is AU$258
includes taxes & fees
23 Feb - 24 Feb
Modern 1BR in Historic HydePark

Studio Apt Comfy & Sunlit

Studio Apt Comfy & Sunlit
Hyde Park
10.0 out of 10, Exceptional, (2 reviews)
"My stay was really good"
United States
Paramita B.
The price is AU$235
includes taxes & fees
15 Feb - 16 Feb
Studio Apt Comfy & Sunlit

Comfortable Condo in the Heart of Bronzeville by RedAwning

Comfortable Condo in the Heart of Bronzeville by RedAwning
Bronzeville
7.8 out of 10, Good, (6 reviews)
"Very clean, everything needed with in. Manager was easily accessible. "
United States
Rosheena C.
The price is AU$581
includes taxes & fees
1 Mar - 2 Mar
Comfortable Condo in the Heart of Bronzeville by RedAwning

3BR | Complete & Well-Located

3BR | Complete & Well-Located
Hyde Park
7.6 out of 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
Teri D.
The price is AU$327
includes taxes & fees
12 Feb - 13 Feb
3BR | Complete & Well-Located
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top South Side Hotel Reviews

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, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect South Side holiday rental for you by simply entering your desired dates. Then check your favourite 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 depend 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 AU$220 per night. Entering your travel dates in the search wizard might find you 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.