A cityscape with a prominent building with a green dome, surrounded by greenery and a body of water.

South Side Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for South Side vacation rentals

A neatly arranged bedroom with a bed, bedside tables, and abstract wall art.

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, (1 review)
"Such a cozy stay! Definitely recommend!"
United States
Angelina
$160 nightly
The price is $178
Nov 16 - Nov 17
Total with taxes and fees
Hyde Park Trendy Studio Apartment in Good Spot
Kitchen

2. 1BR in Prime Hyde Park Apartment

1BR in Prime Hyde Park Apartment
Hyde Park
$224 nightly
The price is $244
Nov 15 - Nov 16
Total with taxes and fees
1BR in Prime Hyde Park Apartment
A neatly made bed with pillows, a bedside lamp, and a small table with a lamp. There are two abstract paintings on the wall above the bed.

3. Trendy Studio Apartment in Chicago

Trendy Studio Apartment in Chicago
Hyde Park
$214 nightly
The price is $234
Nov 3 - Nov 4
Total with taxes and fees
Trendy Studio Apartment in Chicago
A modern living room with a grey sofa, a dining table with chairs, and a kitchen area with a kettle.

4. Perfect 1BR Spot near Attractions

Perfect 1BR Spot near Attractions
Hyde Park
$225 nightly
The price is $245
Nov 9 - Nov 10
Total with taxes and fees
Perfect 1BR Spot near Attractions
A modern living room with a sofa, coffee table, and TV. There are windows with blinds, a radiator, and a plant.

5. 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.
$228 nightly
The price is $254
Nov 15 - Nov 16
Total with taxes and fees
Sleek & Functional 2-Bedroom Apt
Room

6. Cozy Well-Equipped Studio Apartment

Cozy Well-Equipped Studio Apartment
Hyde Park
$219 nightly
The price is $239
Nov 11 - Nov 12
Total with taxes and fees
Cozy Well-Equipped Studio Apartment
A hotel room with a bed, a desk, a chair, a sofa, a ceiling fan, a TV, and artwork on the walls.

7. Elevated Hyde Park Studio Unit on Dorchester Ave

Elevated Hyde Park Studio Unit on Dorchester Ave
Hyde Park
$208 nightly
The price is $226
Nov 2 - Nov 3
Total with taxes and fees
Elevated Hyde Park Studio Unit on Dorchester Ave
A modern living room with a large window, a brown sofa, a coffee table, and a flat-screen TV.

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

Modern Hyde Park 1BR Apt with Workspace & Smart TV
Kenwood
$230 nightly
The price is $251
Nov 3 - Nov 4
Total with taxes and fees
Modern Hyde Park 1BR Apt with Workspace & Smart TV
A living room with hardwood flooring, a ceiling fan, a television, a sofa, a coffee table, and a potted plant.

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

Homey Vibes 1BR Apt near Lake Michigan & UChicago
Kenwood
$239 nightly
The price is $261
Nov 12 - Nov 13
Total with taxes and fees
Homey Vibes 1BR Apt near Lake Michigan & UChicago
A modern apartment with a kitchen, a living area with a sofa, and large windows.

10. Cozy Chicago Apartment Near UChicago

Cozy Chicago Apartment Near UChicago
Kenwood
$217 nightly
The price is $237
Nov 8 - Nov 9
Total with taxes and fees
Cozy Chicago Apartment Near UChicago
A living room with a flat-screen TV on a wooden stand, a glass coffee table, a dining area with two chairs, and a potted plant.

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

Charming Hyde Park 1BR | Fully Furnished & Ready
Hyde Park
$244 nightly
The price is $267
Nov 9 - Nov 10
Total with taxes and fees
Charming Hyde Park 1BR | Fully Furnished & Ready
A neatly made bed with two pillows, a folded towel, and two bedside lamps.

12. Bright & Cozy 1BR Near UChicago

Bright & Cozy 1BR Near UChicago
Hyde Park
$247 nightly
The price is $271
Nov 9 - Nov 10
Total with taxes and fees
Bright & Cozy 1BR Near UChicago
A modern living room with a flat-screen TV, a round glass coffee table, a sofa, and a brown armchair.

13. Bright & Modern 1BR in a Prime Area

Bright & Modern 1BR in a Prime Area
Hyde Park
$223 nightly
The price is $242
Nov 3 - Nov 4
Total with taxes and fees
Bright & Modern 1BR in a Prime Area
Living area

14. Cozy Hyde Park Apartment | Near Lake & UChicago

Cozy Hyde Park Apartment | Near Lake & UChicago
Hyde Park
$235 nightly
The price is $257
Nov 4 - Nov 5
Total with taxes and fees
Cozy Hyde Park Apartment | Near Lake & UChicago
A neatly made bed with a black headboard, two bedside lamps, and a framed picture above the bed.

15. Hyde Park 1BR Apt | Easy & Fully Equipped Stay

Hyde Park 1BR Apt | Easy & Fully Equipped Stay
Hyde Park
$261 nightly
The price is $287
Nov 17 - Nov 18
Total with taxes and fees
Hyde Park 1BR Apt | Easy & Fully Equipped Stay
A living room with a sectional sofa, a glass coffee table, a round table with chairs, and large windows with blinds.

16. Bright 1BR Unit in a Prime Spot

Bright 1BR Unit in a Prime Spot
Hyde Park
$220 nightly
The price is $239
Nov 10 - Nov 11
Total with taxes and fees
Bright 1BR Unit in a Prime Spot
Living area

17. Modern 1BR in Historic HydePark

Modern 1BR in Historic HydePark
Hyde Park
$247 nightly
The price is $271
Nov 9 - Nov 10
Total with taxes and fees
Modern 1BR in Historic HydePark
A modern living room with a sofa, a dining table with chairs, a TV, and a large window with a view of buildings.

18. Sunlit 2BR - Fully Furnished & Spacious Apartment

Sunlit 2BR - Fully Furnished & Spacious Apartment
Kenwood
$219 nightly
The price is $244
Nov 15 - Nov 16
Total with taxes and fees
Sunlit 2BR - Fully Furnished & Spacious Apartment
A bedroom with a bed, desk, chair, and two bedside lamps.

19. 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.
$336 nightly
The price is $362
Nov 2 - Nov 3
Total with taxes and fees
Group-Friendly 4BR Hyde Park Retreat Near UChicago
A living room with a grey sofa, two chairs, a coffee table, and a small side table.

20. 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
$245 nightly
The price is $275
Nov 10 - Nov 11
Total with taxes and fees
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
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

SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown

8/10 Good
"I had a wonderful stay at this hotel! The room was exceptionally clean, fresh, and well-maintained. The entire property was neat and inviting, making my stay comfortable and relaxing. Cleanliness is very important to me, and this hotel exceeded my expectations. I would definitely recommend it and look forward to staying here again!"
Renee 2-night trip
Posted 5 hours ago
SpringHill Suites by Marriott Chicago Chinatown

Find out more about South Side

Everything you need to know about South Side vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the South Side vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

South Side vacation 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 low season months. For more hustle and bustle, you may prefer to visit South Side in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on South Side rentals

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

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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