South Side Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in South Side

Stylish Apartment near Chicago Downtown

2.0 star property
The price is AU$384
includes taxes & fees
1 Oct - 2 Oct
Stylish Apartment near Chicago Downtown

Cozy Studio in Hyde Park-Walk to Lake & University

9.0 out of 10, Wonderful, (6)
"This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. "
The price is AU$274
includes taxes & fees
1 Oct - 2 Oct
Cozy Studio in Hyde Park-Walk to Lake & University

Modern Studio Near UChicago

10.0 out of 10, Exceptional, (3)
"Great location. Clean, nicely decorated room. "
The price is AU$274
includes taxes & fees
7 Oct - 8 Oct
Modern Studio Near UChicago

Modern 1BR in Historic HydePark

10.0 out of 10, Exceptional, (2)
"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!"
The price is AU$289
includes taxes & fees
1 Oct - 2 Oct
Modern 1BR in Historic HydePark

LakeHouse

9.4 out of 10, Exceptional, (21)
"Everything was perfect with the property and the host even came to help right away when we had one issue with the lights."
LakeHouse

Cheerful 4 bedroom smart home w/ indoor fireplace

8.0 out of 10, Very good, (16)
"The property is shown accurately in the photos. It was pretty clean. Its centrally located to eateries and shopping. Need more pillows, had no window coverings and had to contact tbe host for the correct code to the door.Would stay again."
Cheerful 4 bedroom smart home w/ indoor fireplace

A Home Away From Home!

9.6 out of 10, Exceptional, (11)
"Great place to stay. Host responded quickly to questions. Location was good and neighbor was quite. "
A Home Away From Home!

Explore Hyde Park: 2BR Apt on Blackstone Ave

The price is AU$332
includes taxes & fees
1 Oct - 2 Oct
Explore Hyde Park: 2BR Apt on Blackstone Ave

Mayors Manor, Zen Garden Oasis, Hot Tub & Sauna in Central Chicago, 8-12 guests

9.4 out of 10, Exceptional, (17)
"The owners were SUPER helpful and their communication was SUPERB!"
Mayors Manor, Zen Garden Oasis, Hot Tub & Sauna in Central Chicago, 8-12 guests

Animal House Near Sox Stadium

8.0 out of 10, Very good, (10)
"It was very cute! I enjoyed staying here"
Animal House Near Sox Stadium

Comfortable Condo in the Heart of Bronzeville by RedAwning

7.2 out of 10, Good, (5)
"There was confusion with VRBO regarding our arrival date, no fault of the property owner. They made arrangements to clean the unit and provide lunch for our group while we waited and offered a second night free for the inconvenience. Highly recommend. Property owner went above and beyond!"
Comfortable Condo in the Heart of Bronzeville by RedAwning

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

9.8 out of 10, Exceptional, (9)
"I went with 4 other friends, and this place was super clean, came with everything we needed, and even includes a cute small gaming room! Definitely would stay again!"
Stay near family or close to downtown, this loft in Beverly has it all!

Bright & Spacious 2BR– Prime Hyde Park Location

The price is AU$350
includes taxes & fees
1 Oct - 2 Oct
Bright & Spacious 2BR– Prime Hyde Park Location

House with garage, outdoor dining and basement bar

7.4 out of 10, Good, (3)
"Property was very clean, warm and welcoming. Beds were comfortable. Property manager was great at checking in, and readily available. The place smells great! Everything is new! We will definitely book again!"
House with garage, outdoor dining and basement bar

Chic Retreat: Cozy 1BR Apartment

10.0 out of 10, Exceptional, (3)
"Our stay was very nice, with simple checkin / check out, and excellent communication by our host. "
The price is AU$289
includes taxes & fees
1 Oct - 2 Oct
Chic Retreat: Cozy 1BR Apartment

Lovely cozy 2 Bedroom Private Suite In Historical Beverly Community

9.0 out of 10, Wonderful, (27)
"Very comfortable, enjoyed my stay "
Lovely cozy 2 Bedroom Private Suite In Historical Beverly Community

South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly

10.0 out of 10, Exceptional, (1)
"Clean apartment and great communication with host. Fixed any small problems very quickly. "
South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly

Sleek & Functional 2-Bedroom Apt

9.4 out of 10, Exceptional, (3)
"I really enjoyed my stay at this property! Everything was exactly as described and the property was exceptionally clean and centrally located. The check-in process was smooth and the hosts were very communicative from booking to check-out. "
The price is AU$332
includes taxes & fees
1 Oct - 2 Oct
Sleek & Functional 2-Bedroom Apt

3BR | Complete & Well-Located

8.0 out of 10, Very good, (2)
"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."
The price is AU$463
includes taxes & fees
21 Oct - 22 Oct
3BR | Complete & Well-Located

Dalia Flat - Sleeps 10 - 10 minutes to Downtown

9.4 out of 10, Exceptional, (14)
"Beautiful place to stay while passing through Chicago! Family friendly and clean. "
The price is AU$451
includes taxes & fees
14 Oct - 15 Oct
Dalia Flat - Sleeps 10 - 10 minutes to Downtown
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.
Save an average of 15% on thousands of hotels when you're signed in

Top South Side Hotel Reviews

Find out more about South Side

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$274 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.