Best Apartments in South Side for Your Vacation from ￥10,237

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Our top choices for South Side apartments

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

1. Hyde Park Trendy Studio Apartment in Good Spot

Hyde Park

Angelina

￥23,773 total

includes taxes & fees

Nov 12 - Nov 13

A modern living room with a grey sofa, a dining table with chairs, and a kitchen area with a kettle.

2. Perfect 1BR Spot near Attractions

Hyde Park

Andrew M.

￥33,544 total

includes taxes & fees

Nov 9 - Nov 10

A modern living room with a sofa, coffee table, and TV. There are windows with blinds, a radiator, and a plant.

3. Sleek & Functional 2-Bedroom Apt

Hyde Park

Lisa T.

￥36,615 total

includes taxes & fees

Nov 10 - Nov 11

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.

4. Trendy Studio Apartment in Chicago

Hyde Park

￥32,232 total

includes taxes & fees

Nov 24 - Nov 25

A living room with hardwood flooring, a ceiling fan, a television, a sofa, a coffee table, and a potted plant.

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

Kenwood

￥33,755 total

includes taxes & fees

Nov 9 - Nov 10

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.

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

Hyde Park

￥35,950 total

includes taxes & fees

Nov 9 - Nov 10

A modern kitchen with a double sink, stainless steel appliances, and white cabinetry.

7. 1BR Chic Apt in Downtown Chicago

Hyde Park

￥37,564 total

includes taxes & fees

Nov 10 - Nov 11

A neatly made bed with two pillows, a folded towel, and two bedside lamps.

8. Bright & Cozy 1BR Near UChicago

Hyde Park

￥37,894 total

includes taxes & fees

Nov 8 - Nov 9

A living room with a sectional sofa, a glass coffee table, a round table with chairs, and large windows with blinds.

9. Bright 1BR Unit in a Prime Spot

Hyde Park

￥34,368 total

includes taxes & fees

Nov 10 - Nov 11

10. Cozy Well-Equipped Studio Apartment

Hyde Park

￥33,163 total

includes taxes & fees

Nov 10 - Nov 11

A modern hotel room with a bed, a sofa, a coffee table, a TV, and a kitchenette.

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

Kenwood

￥37,330 total

includes taxes & fees

Nov 10 - Nov 11

12. Cozy Hyde Park Apartment | Near Lake & UChicago

Hyde Park

￥35,803 total

includes taxes & fees

Nov 9 - Nov 10

A modern living room with a large window, a brown sofa, a coffee table, and a flat-screen TV.

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

Kenwood

￥33,411 total

includes taxes & fees

Nov 10 - Nov 11

14. Modern 1BR in Historic HydePark

Hyde Park

￥36,176 total

includes taxes & fees

Nov 9 - Nov 10

A hotel room with a bed, a desk, a chair, a sofa, a ceiling fan, a TV, and artwork on the walls.

15. Elevated Hyde Park Studio Unit on Dorchester Ave

Hyde Park

￥34,454 total

includes taxes & fees

Nov 15 - Nov 16

A modern living room with a flat-screen TV, a round glass coffee table, a sofa, and a brown armchair.

16. Bright & Modern 1BR in a Prime Area

Hyde Park

￥36,358 total

includes taxes & fees

Nov 10 - Nov 11

A bedroom with a bed, desk, chair, and two bedside lamps.

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

Hyde Park

Cuoghi E.

￥53,134 total

includes taxes & fees

Nov 10 - Nov 11

A neatly made bed with a black headboard, two bedside lamps, and a framed picture above the bed.

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

Hyde Park

￥39,738 total

includes taxes & fees

Nov 15 - Nov 16

A modern living room with a sofa, a dining table with chairs, a TV, and a large window with a view of buildings.

19. Sunlit 2BR - Fully Furnished & Spacious Apartment

Kenwood

￥33,645 total

includes taxes & fees

Nov 23 - Nov 24

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

Brighton Park

Rachel

￥36,100 total

includes taxes & fees

Nov 9 - Nov 10

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Learn more about South Side

Discover the metropolitan area of South Side—museums, skyscrapers, and top sights like Lake Michigan.

See all hotels in South Side

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

Top reviews in South Side

A two-story house with a brick exterior, a sloped roof, and a front porch.

At Home in Oak Park

Oak Park

10/10 Excellent

Melissa

A modern building with large glass windows, surrounded by a grassy area with trees and a pathway.

The Oak Park Loft

Oak Park

10/10 Excellent

The loft was clean and well cared for. Adjustable thermostats for each area. Bathroom was beautiful and there was a double sink and large shower. There are some games in the living room for downtime. There is a Green line on the L just a 10 minute walk away that gets you straight to downtown Chicago. My daughter LOVED her bed as well as the all stuffies that they were decorated with. There is an included garage space, and 2 sets of washers and dryers downstairs if needed. This was a great way...

April

A spacious living room with a grand piano, a comfortable sofa, and a dining area with a chandelier.

Historic Oak Park Home

Oak Park

10/10 Excellent

judith

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Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for South Side apartments

1. Hyde Park Trendy Studio Apartment in Good Spot

2. Perfect 1BR Spot near Attractions

3. Sleek & Functional 2-Bedroom Apt

4. Trendy Studio Apartment in Chicago

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

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

7. 1BR Chic Apt in Downtown Chicago

8. Bright & Cozy 1BR Near UChicago

9. Bright 1BR Unit in a Prime Spot

10. Cozy Well-Equipped Studio Apartment

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

12. Cozy Hyde Park Apartment | Near Lake & UChicago

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

14. Modern 1BR in Historic HydePark

15. Elevated Hyde Park Studio Unit on Dorchester Ave

16. Bright & Modern 1BR in a Prime Area

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

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

19. Sunlit 2BR - Fully Furnished & Spacious Apartment

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

Learn more about South Side

Top reviews in South Side

At Home in Oak Park

10/10 Excellent

Historic Oak Park Residence

10/10 Excellent

The Oak Park Loft

10/10 Excellent

Historic Oak Park Home

10/10 Excellent

Explore a world of travel with Expedia

Apartments in South Side for Rent

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for South Side apartments

1. Hyde Park Trendy Studio Apartment in Good Spot

2. Perfect 1BR Spot near Attractions

3. Sleek & Functional 2-Bedroom Apt

4. Trendy Studio Apartment in Chicago

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

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

7. 1BR Chic Apt in Downtown Chicago

8. Bright & Cozy 1BR Near UChicago

9. Bright 1BR Unit in a Prime Spot

10. Cozy Well-Equipped Studio Apartment

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

12. Cozy Hyde Park Apartment | Near Lake & UChicago

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

14. Modern 1BR in Historic HydePark

15. Elevated Hyde Park Studio Unit on Dorchester Ave

16. Bright & Modern 1BR in a Prime Area

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

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

19. Sunlit 2BR - Fully Furnished & Spacious Apartment

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

Learn more about South Side

Top reviews in South Side

At Home in Oak Park

10/10 Excellent

Explore a world of travel with Expedia