South Side Holiday Rentals

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Our top choices for South Side holiday rentals

1. Hyde Park Trendy Studio Apartment in Good Spot

Hyde Park Trendy Studio Apartment in Good Spot
Hyde Park
10.0 out of 10, Exceptional, (2 reviews)
"Location could not be beat of looking to be near University of Chicago. Within walking distance to several restaurants, coffee, shops, and stores. Perfect for our trip!"
United States
rebecca
The price is AU$222
includes taxes & fees
12 Nov - 13 Nov
Hyde Park Trendy Studio Apartment in Good Spot

2. Perfect 1BR Spot near Attractions

Perfect 1BR Spot near Attractions
Hyde Park
6.0 out of 10, (1 review)
"I would characterize this property as “fine”. I only needed to stay one night for a business trip and it got the job done. Getting in/out was a little cumbersome with a lockbox to retrieve a set of keys. Hot water took quite a long time to heat up and deliver for a shower. Shower bathtub and amenities were lacking. Again, it got the job done for a night of sleep."
United States
Andrew M.
The price is AU$325
includes taxes & fees
10 Nov - 11 Nov
Perfect 1BR Spot near Attractions

3. Sleek & Functional 2-Bedroom Apt

Sleek & Functional 2-Bedroom Apt
Hyde Park
10.0 out of 10, Exceptional, (1 review)
"Great place, great location!"
United States
Lisa T.
The price is AU$299
includes taxes & fees
11 Nov - 12 Nov
Sleek & Functional 2-Bedroom Apt

4. Homey Vibes 1BR Apt near Lake Michigan & UChicago

Homey Vibes 1BR Apt near Lake Michigan & UChicago
Kenwood
The price is AU$337
includes taxes & fees
15 Nov - 16 Nov
Homey Vibes 1BR Apt near Lake Michigan & UChicago

5. Conveniently Situated 1BR Apartment

Conveniently Situated 1BR Apartment
Hyde Park
10.0 out of 10, Exceptional, (1 review)
"Cute, cozy place in walking distance to UChicago. Would stay here again."
United States
Jane L.
The price is AU$325
includes taxes & fees
10 Nov - 11 Nov
Conveniently Situated 1BR Apartment

6. Charming Hyde Park 1BR | Fully Furnished & Ready

Charming Hyde Park 1BR | Fully Furnished & Ready
Hyde Park
The price is AU$318
includes taxes & fees
10 Nov - 11 Nov
Charming Hyde Park 1BR | Fully Furnished & Ready

7. Bright 1BR Unit in a Prime Spot

Bright 1BR Unit in a Prime Spot
Hyde Park
The price is AU$318
includes taxes & fees
10 Nov - 11 Nov
Bright 1BR Unit in a Prime Spot

8. Bright & Cozy 1BR Near UChicago

Bright & Cozy 1BR Near UChicago
Hyde Park
The price is AU$311
includes taxes & fees
10 Nov - 11 Nov
Bright & Cozy 1BR Near UChicago

9. 1BR in Prime Hyde Park Apartment

1BR in Prime Hyde Park Apartment
Hyde Park
6.0 out of 10, (1 review)
"Location was great since we were visiting the University of Chicago and the apartment matches the pictures but there were other issues. First problem was at the building entrance, both lockboxes were empty so I had no key to enter the building. I messaged the host but had to wait for a response; luckily someone exited the building and let me in. Second problem was there was a draft in each room of the apartment and none of the radiators worked. There was a small electric heater in the closet...
United States
Rebecca
The price is AU$318
includes taxes & fees
10 Nov - 11 Nov
1BR in Prime Hyde Park Apartment

10. Cozy Well-Equipped Studio Apartment

Cozy Well-Equipped Studio Apartment
Hyde Park
The price is AU$305
includes taxes & fees
10 Nov - 11 Nov
Cozy Well-Equipped Studio Apartment

11. Group-Friendly 4BR Hyde Park Retreat Near UChicago

Group-Friendly 4BR Hyde Park Retreat Near UChicago
Hyde Park
6.8 out of 10, (6 reviews)
"Pretty standard for a VRBO property. No frills but excellent location and great that it had 4 bedrooms for our group. "
United States
Cuoghi E.
The price is AU$452
includes taxes & fees
10 Nov - 11 Nov
Group-Friendly 4BR Hyde Park Retreat Near UChicago

12. Relaxed City Stay in Hyde Park | Cozy Studio Unit

Relaxed City Stay in Hyde Park | Cozy Studio Unit
Kenwood
The price is AU$378
includes taxes & fees
12 Nov - 13 Nov
Relaxed City Stay in Hyde Park | Cozy Studio Unit

13. Bright & Modern 1BR in a Prime Area

Bright & Modern 1BR in a Prime Area
Hyde Park
The price is AU$305
includes taxes & fees
10 Nov - 11 Nov
Bright & Modern 1BR in a Prime Area

14. Modern Hyde Park 1BR Apt with Workspace & Smart TV

Modern Hyde Park 1BR Apt with Workspace & Smart TV
Kenwood
The price is AU$312
includes taxes & fees
11 Nov - 12 Nov
Modern Hyde Park 1BR Apt with Workspace & Smart TV

15. Trendy Studio Apartment in Chicago

Trendy Studio Apartment in Chicago
Hyde Park
The price is AU$300
includes taxes & fees
24 Nov - 25 Nov
Trendy Studio Apartment in Chicago

16. Bright & Spacious 2BR– Prime Hyde Park Location

Bright & Spacious 2BR– Prime Hyde Park Location
Hyde Park
The price is AU$305
includes taxes & fees
10 Nov - 11 Nov
Bright & Spacious 2BR– Prime Hyde Park Location

17. Modern 1BR in Historic HydePark

Modern 1BR in Historic HydePark
Hyde Park
The price is AU$318
includes taxes & fees
10 Nov - 11 Nov
Modern 1BR in Historic HydePark

18. Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Brighton Park
10.0 out of 10, Exceptional, (2 reviews)
"The rooms were spotless. The apartment was spacious. I enjoyed my stay. "
United States
Rachel
The price is AU$350
includes taxes & fees
10 Nov - 11 Nov
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

19. Elevated Hyde Park Studio Unit on Dorchester Ave

Elevated Hyde Park Studio Unit on Dorchester Ave
Hyde Park
The price is AU$318
includes taxes & fees
15 Nov - 16 Nov
Elevated Hyde Park Studio Unit on Dorchester Ave

20. Sunlit 2BR - Fully Furnished & Spacious Apartment

Sunlit 2BR - Fully Furnished & Spacious Apartment
Kenwood
The price is AU$325
includes taxes & fees
24 Nov - 25 Nov
Sunlit 2BR - Fully Furnished & Spacious Apartment
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.

Find holiday rentals that suit your style

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 chosen for you start as low as AU$221 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.

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