South Side Holiday Rentals

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Holiday Rentals in South Side

Cozy Studio in Hyde Park-Walk to Lake & University

10.0 out of 10, Exceptional, (2)
"This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. "
The price is AU$297
includes taxes & fees
2 Sept - 3 Sept
Cozy Studio in Hyde Park-Walk to Lake & University

A Home Away From Home!

9.6 out of 10, Exceptional, (9)
"Great place to stay. Host responded quickly to questions. Location was good and neighbor was quite. "
A Home Away From Home!

Sleek & Functional 2-Bedroom Apt

10.0 out of 10, Exceptional, (2)
"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$339
includes taxes & fees
2 Sept - 3 Sept
Sleek & Functional 2-Bedroom Apt

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

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

LakeHouse

9.2 out of 10, Wonderful, (20)
"Everything was perfect with the property and the host even came to help right away when we had one issue with the lights."
LakeHouse

Comfortable Condo in the Heart of Bronzeville by RedAwning

6.6 out of 10, (4)
"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!"
The price is AU$625
includes taxes & fees
2 Sept - 3 Sept
Comfortable Condo in the Heart of Bronzeville by RedAwning

Lovely cozy 2 Bedroom Private Suite In Historical Beverly Community

9.0 out of 10, Wonderful, (23)
"Very comfortable, enjoyed my stay "
Lovely cozy 2 Bedroom Private Suite In Historical Beverly Community

Marvelous 3-bedroom apartment with WiFi, AC 18 minutes from downtown Chicago

8.6 out of 10, Excellent, (8)
"Very nice stay. Very clean, plenty of room, great location from Downtown Chicago. "
Marvelous 3-bedroom apartment with WiFi, AC 18 minutes from downtown Chicago

Cozy 1-bedroom apartment with WiFi, AC in gorgeous Chicago

2.0 star property
9.8 out of 10, Exceptional, (11)
"Served us well for our event near the McCormick Center. Hospitality was second to none! "
Cozy 1-bedroom apartment with WiFi, AC in gorgeous Chicago

Studio Apt Comfy & Sunlit

The price is AU$319
includes taxes & fees
3 Sept - 4 Sept
Studio Apt Comfy & Sunlit

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 1-bedroom apartment in marvelous Chicago with WiFi, AC.

Chic 1-bedroom apartment in marvelous Chicago with WiFi, AC.

Modern Condo-Obama & University of Chicago Area

8.8 out of 10, Excellent, (13)
"I thought this place was so cute, loved the outset deck! Was spacious and the host was very nice and helpful when needed! Would stay again for sure! "
Modern Condo-Obama & University of Chicago Area

Chic 1-bedroom apartment,15mims from downtown

9.0 out of 10, Wonderful, (2)
"Stayed here to work C2E2 for the weekend. Great big space with everything I needed to rest up after a long day of work."
Chic 1-bedroom apartment,15mims from downtown

Dalia Flat - Sleeps 10 - 10 minutes to Downtown

9.4 out of 10, Exceptional, (14)
"Nice amenities, and centrally located, grocery store near, nice full kitchen, nothing we didn’t like about."
The price is AU$421
includes taxes & fees
2 Sept - 3 Sept
Dalia Flat - Sleeps 10 - 10 minutes to Downtown

Perfect 1BR Spot near Attractions

7.2 out of 10, Good, (5)
"Freshly painted and clean. Hosts were responsive. Everything we needed for our stay. Walkable area. "
The price is AU$313
includes taxes & fees
2 Sept - 3 Sept
Perfect 1BR Spot near Attractions

Explore Hyde Park: 2BR Apt on Blackstone Ave

The price is AU$339
includes taxes & fees
2 Sept - 3 Sept
Explore Hyde Park: 2BR Apt on Blackstone Ave

Come experience The Lake Shore!

10.0 out of 10, Exceptional, (2)
"Very spacious, quiet and comfortable. Great place to stay!"
Come experience The Lake Shore!

Modern 1BR in Historic HydePark

10.0 out of 10, Exceptional, (1)
"Comfortable space. All the necessary amenities. Extremely walkable to everything.Will stay again. "
The price is AU$313
includes taxes & fees
2 Sept - 3 Sept
Modern 1BR in Historic HydePark

Toca Bella ~ 7mins to Downtown

9.8 out of 10, Exceptional, (16)
"We had a nice stay at this VRBO apartment, pretty quiet, had what we needed for a quick trip. Easy access, not much problem finding street parking in a busy neighborhood. "
Toca Bella ~ 7mins 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.
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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$297 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.