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

South Side Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for South Side holiday rentals

A modern kitchen with a stainless steel refrigerator, a stove, and white cabinets.

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
The price is HK$526
HK$1,280 total
includes taxes & fees
27 Oct - 28 Oct
Hyde Park Trendy Studio Apartment in Good Spot
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.

2. 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 HK$832
HK$1,913 total
includes taxes & fees
2 Nov - 3 Nov
Sleek & Functional 2-Bedroom Apt
A living room with a flat-screen TV, a sofa, a coffee table, and a staircase leading to another room.

3. Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Brighton Park
8.6 out of 10, Excellent, (21 reviews)
"Excellent location and go anywhere so close."
United States
Yiu S.
The price is HK$698
HK$1,947 total
includes taxes & fees
1 Nov - 2 Nov
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Private kitchen

4. ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago

ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago
Kenwood
10.0 out of 10, Exceptional, (5 reviews)
"Exactly as described, would recommend"
United States
Anonymous traveller
The price is HK$1,452
HK$4,126 total
includes taxes & fees
20 Oct - 21 Oct
ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago
A modern kitchen with white cabinets, stainless steel appliances, and a black countertop.

5. 3BR | Complete & Well-Located Apt in Hyde Park

3BR | Complete & Well-Located Apt in Hyde Park
Hyde Park
7.6 out of 10, Good, (5 reviews)
"Enjoyed our stay. Thank you"
United States
Nicolle C.
The price is HK$855
HK$2,077 total
includes taxes & fees
26 Oct - 27 Oct
3BR | Complete & Well-Located Apt in Hyde Park
A bedroom with a bed, desk, chair, and two bedside lamps.

6. 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 HK$855
HK$2,882 total
includes taxes & fees
26 Oct - 27 Oct
Group-Friendly 4BR Hyde Park Retreat Near UChicago
A grey sectional sofa with six cushions against a white wall, a black coffee table in front, and a cityscape artwork above.

7. 4BR Downtown Retreat | Free Street Parking

4BR Downtown Retreat | Free Street Parking
Armour Square
10.0 out of 10, Exceptional, (1 review)
"The house was very clean, and in a family friendly neighborhood within walking distance of the CTA train (no driving all over Chicago.) Tony the host was very responsive and prompt to correct the issue of the thermostat not working. Overall I would say that it was a very pleasant experience!"
United States
Brandon S.
The price is HK$1,634
HK$4,470 total
includes taxes & fees
25 Oct - 26 Oct
4BR Downtown Retreat | Free Street Parking
Kitchen

8. 1BR in Prime Hyde Park Apartment

1BR in Prime Hyde Park Apartment
Hyde Park
The price is HK$549
HK$1,847 total
includes taxes & fees
15 Nov - 16 Nov
1BR in Prime Hyde Park Apartment
A kitchen with a stainless steel stove, oven, and microwave, with a clock on the wall.

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

Bright & Spacious 2BR– Prime Hyde Park Location
Hyde Park
The price is HK$848
HK$1,970 total
includes taxes & fees
26 Oct - 27 Oct
Bright & Spacious 2BR– Prime Hyde Park Location
A modern living room with a grey sofa, a coffee table, and a view of the outside through large windows.

10. Conveniently Situated 1BR Apartment

Conveniently Situated 1BR Apartment
Hyde Park
The price is HK$698
HK$2,041 total
includes taxes & fees
2 Nov - 3 Nov
Conveniently Situated 1BR Apartment
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
The price is HK$808
HK$2,170 total
includes taxes & fees
11 Nov - 12 Nov
Charming Hyde Park 1BR | Fully Furnished & Ready
A modern kitchen with white cabinets, a stainless steel refrigerator, a black countertop, and three bar stools.

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

Relaxed City Stay in Hyde Park | Cozy Studio Unit
Kenwood
The price is HK$510
HK$1,801 total
includes taxes & fees
19 Oct - 20 Oct
Relaxed City Stay in Hyde Park | Cozy Studio Unit
A hotel room with a bed, two bedside lamps, a red throw blanket, and a wall-mounted abstract painting.

13. Sunlit 2BR - Fully Furnished & Spacious Apartment

Sunlit 2BR - Fully Furnished & Spacious Apartment
Kenwood
The price is HK$848
HK$1,922 total
includes taxes & fees
26 Oct - 27 Oct
Sunlit 2BR - Fully Furnished & Spacious Apartment
A living room with a round glass coffee table, a dark sofa, and two abstract paintings on the wall.

14. Bright & Modern 1BR in a Prime Area

Bright & Modern 1BR in a Prime Area
Hyde Park
The price is HK$644
HK$1,976 total
includes taxes & fees
27 Oct - 28 Oct
Bright & Modern 1BR in a Prime Area
A kitchen with a stainless steel stove, a wooden utensil holder, and a granite countertop.

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

Homey Vibes 1BR Apt near Lake Michigan & UChicago
Kenwood
Homey Vibes 1BR Apt near Lake Michigan & UChicago
A small kitchenette with a white refrigerator, a coffee maker, a toaster, and a shelf with various items.

16. Perfect 1BR Spot near Attractions

Perfect 1BR Spot near Attractions
Hyde Park
The price is HK$604
HK$1,921 total
includes taxes & fees
25 Oct - 26 Oct
Perfect 1BR Spot near Attractions
A kitchen with white cabinets, a gas stove, a sink, and a coffee maker.

17. Elevated Hyde Park Studio Unit on Dorchester Ave

Elevated Hyde Park Studio Unit on Dorchester Ave
Hyde Park
The price is HK$581
HK$1,805 total
includes taxes & fees
3 Nov - 4 Nov
Elevated Hyde Park Studio Unit on Dorchester Ave
A neatly made bed with two pillows, a folded towel, and two bedside lamps.

18. Bright & Cozy 1BR Near UChicago

Bright & Cozy 1BR Near UChicago
Hyde Park
The price is HK$683
HK$2,032 total
includes taxes & fees
25 Oct - 26 Oct
Bright & Cozy 1BR Near UChicago
Kitchen

19. Modern 1BR in Historic HydePark

Modern 1BR in Historic HydePark
Hyde Park
The price is HK$698
HK$2,050 total
includes taxes & fees
2 Nov - 3 Nov
Modern 1BR in Historic HydePark
A small round table with two chairs, a potted plant, and a view of trees through a window.

20. Bright 1BR Unit in a Prime Spot

Bright 1BR Unit in a Prime Spot
Hyde Park
The price is HK$714
HK$2,059 total
includes taxes & fees
2 Nov - 3 Nov
Bright 1BR Unit in a Prime Spot
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

Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

8/10 Good
"From outside hotel looks uninviting, but room was clean, AC worked well and bed was comfortable. Internet did not work most of the morning but it worked at night. Hotel was fine for a short stay."
Laura 2-night trip
Posted 13 hours ago
Chicago Lake Shore Hotel

Find out more about South Side

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