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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for South Side vacation rentals

A living room with a round glass coffee table, a dark sofa, and two abstract paintings on the wall.

1. Bright & Modern 1BR in a Prime Area

Bright & Modern 1BR in a Prime Area
Hyde Park
$222 nightly
The price is $241
Oct 20 - Oct 21
Total with taxes and fees
Bright & Modern 1BR in a Prime Area
A kitchen with a stainless steel stove, a wooden utensil holder, and a granite countertop.

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

Homey Vibes 1BR Apt near Lake Michigan & UChicago
Kenwood
$223 nightly
The price is $242
Oct 22 - Oct 23
Total with taxes and fees
Homey Vibes 1BR Apt near Lake Michigan & 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.

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

Charming Hyde Park 1BR | Fully Furnished & Ready
Hyde Park
$223 nightly
The price is $242
Oct 20 - Oct 21
Total with taxes and fees
Charming Hyde Park 1BR | Fully Furnished & Ready
Living area

4. Cozy Hyde Park Apartment | Near Lake & UChicago

Cozy Hyde Park Apartment | Near Lake & UChicago
Hyde Park
$216 nightly
The price is $234
Oct 21 - Oct 22
Total with taxes and fees
Cozy Hyde Park Apartment | Near Lake & UChicago
A modern kitchen with white cabinets, a stainless steel refrigerator, a black countertop, and three bar stools.

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

Relaxed City Stay in Hyde Park | Cozy Studio Unit
Kenwood
$224 nightly
The price is $244
Oct 19 - Oct 20
Total with taxes and fees
Relaxed City Stay in Hyde Park | Cozy Studio Unit
A kitchen with white cabinets, a gas stove, a sink, and a coffee maker.

6. Elevated Hyde Park Studio Unit on Dorchester Ave

Elevated Hyde Park Studio Unit on Dorchester Ave
Hyde Park
$203 nightly
The price is $221
Nov 1 - Nov 2
Total with taxes and fees
Elevated Hyde Park Studio Unit on Dorchester Ave
A modern kitchen with a stainless steel refrigerator, a stove, and white cabinets.

7. 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
$147 nightly
The price is $163
Nov 1 - Nov 2
Total with taxes and fees
Hyde Park Trendy Studio Apartment in Good Spot
A dining area with a round table and two wooden chairs, a white door, and a framed picture on the wall.

8. Cozy Charm Studio Apt in Chicago

Cozy Charm Studio Apt in Chicago
Hyde Park
$197 nightly
The price is $213
Oct 25 - Oct 26
Total with taxes and fees
Cozy Charm Studio Apt in Chicago
A small round table with two chairs, a potted plant, and a view of trees through a window.

9. Bright 1BR Unit in a Prime Spot

Bright 1BR Unit in a Prime Spot
Hyde Park
$244 nightly
The price is $267
Oct 25 - Oct 26
Total with taxes and fees
Bright 1BR Unit in a Prime Spot
A modern kitchen with a stainless steel stove, microwave, and dishwasher.

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

Modern Hyde Park 1BR Apt with Workspace & Smart TV
Kenwood
$215 nightly
The price is $233
Nov 3 - Nov 4
Total with taxes and fees
Modern Hyde Park 1BR Apt with Workspace & Smart TV
A compact kitchen with white cabinets, a gas stove, a microwave, and a trash bin.

11. Cozy Well-Equipped Studio Apartment

Cozy Well-Equipped Studio Apartment
Hyde Park
$203 nightly
The price is $221
Nov 1 - Nov 2
Total with taxes and fees
Cozy Well-Equipped Studio Apartment
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
$240 nightly
The price is $262
Oct 14 - Oct 15
Total with taxes and fees
Bright & Cozy 1BR Near UChicago
Game room

13. Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade

Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade
Brighton Park
9.4 out of 10, Exceptional, (13 reviews)
"It was great it had the basic amenities for a family to enjoy the stay"
United States
Damary T.
$240 nightly
The price is $269
Oct 13 - Oct 14
Total with taxes and fees
Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade
A living room with a grey sofa, two chairs, a coffee table, and a small side table.

14. 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
$240 nightly
The price is $270
Oct 7 - Oct 8
Total with taxes and fees
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
A round table with two chairs, a potted plant, and a vase with flowers. There are two windows with blinds, a radiator, and two framed artworks on the walls.

15. Sleek & Functional 2-Bedroom Apt

Sleek & Functional 2-Bedroom Apt
Hyde Park
$212 nightly
The price is $235
Oct 5 - Oct 6
Total with taxes and fees
Sleek & Functional 2-Bedroom Apt
A small dining area with a round table, two chairs, and a potted plant.

16. 1BR Chic Apt in Downtown Chicago

1BR Chic Apt in Downtown Chicago
Hyde Park
$237 nightly
The price is $259
Oct 4 - Oct 5
Total with taxes and fees
1BR Chic Apt in Downtown Chicago

17. Modern 1BR in Historic HydePark

Modern 1BR in Historic HydePark
Hyde Park
$223 nightly
The price is $242
Oct 22 - Oct 23
Total with taxes and fees
Modern 1BR in Historic HydePark
A hotel room with a bed, two bedside lamps, a red throw blanket, and a wall-mounted abstract painting.

18. Sunlit 2BR - Fully Furnished & Spacious Apartment

Sunlit 2BR - Fully Furnished & Spacious Apartment
Kenwood
$209 nightly
The price is $232
Oct 5 - Oct 6
Total with taxes and fees
Sunlit 2BR - Fully Furnished & Spacious Apartment
A kitchen with a gas stove, a stainless steel sink, and a brick backsplash.

19. Perfect 1BR Spot near Attractions

Perfect 1BR Spot near Attractions
Hyde Park
$237 nightly
The price is $259
Oct 4 - Oct 5
Total with taxes and fees
Perfect 1BR Spot near Attractions
A kitchen with a stainless steel stove, oven, and microwave, with a clock on the wall.

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

Bright & Spacious 2BR– Prime Hyde Park Location
Hyde Park
$238 nightly
The price is $265
Oct 26 - Oct 27
Total with taxes and fees
Bright & Spacious 2BR– Prime Hyde Park Location
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

Motel 6 - Chicago, IL

Motel 6 - Chicago, IL

8/10 Good
"The property is well mentained and I would wish to stay there again . Thank you 👍"
Andrew 5-night trip
Posted 15 hours ago
Motel 6 - Chicago, IL

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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