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

Holiday Homes in South Side

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for South Side holiday homes

A modern bathroom with a large mirror, a sink, and two hanging planters with greenery.

1. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!
Lincoln Park
9.0 out of 10, Wonderful, (2 reviews)
"Property is a bit worn, however, furnishings are in good shape and nicely appointed for our stay. Clean upon arrival and great location for an extended stay in Chicago. Host has extra supplies that are helpful- umbrellas, games, laundry detergent that made our stay easier and more enjoyable. Would stay again."
United States
Sara C.
The price is AU$910
includes taxes & fees
10 Nov - 11 Nov
4 BR • Theater Room • Gym • Walk to Lincoln Park!
A wooden deck with a railing, a staircase, and a window with a wreath.

2. Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Robertsdale
9.8 out of 10, Exceptional, (37 reviews)
"Quiet neighborhood, comfy beds, attentive hosts. Would stay again."
United States
Scott n Holly K.
The price is AU$291
includes taxes & fees
10 Nov - 11 Nov
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

3. Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful night, boys loved the arcade area."
United States
Anonymous traveller
The price is AU$1,232
includes taxes & fees
10 Nov - 11 Nov
Sleeps 18 • 8BR • Game Room • Gym • Theater
A marble countertop with a cheese platter, grapes, nuts, and a bottle of wine.

4. Game Room • Fire-pit • Playground • Gym • Billiard

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
9.6 out of 10, Exceptional, (5 reviews)
"Everyone was super happy with the house and the location."
United States
Rhiannon
The price is AU$643
includes taxes & fees
10 Nov - 11 Nov
Game Room • Fire-pit • Playground • Gym • Billiard
A cozy living room with a neon sign, a fireplace, a television, and a guitar.

5. Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops

Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
Lincoln Park
9.6 out of 10, Exceptional, (45 reviews)
"Great location. Great place to stay. "
United States
Jill L.
The price is AU$803
includes taxes & fees
10 Nov - 11 Nov
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
A covered patio with a hammock, a barbecue grill, and a dining area with a table and chairs.

6. Chicago Riverhouse with private fenced in oasis

Chicago Riverhouse with private fenced in oasis
North Park
10.0 out of 10, Exceptional, (45 reviews)
"House was perfect for our needs and all as described per the listing."
United States
Robert S.
Chicago Riverhouse with private fenced in oasis
Step into a bright, airy space where comfort and style flow seamlessly from the cozy living area into a chic dining room. Whether you're curled up on the sectional with a blanket and coffee or gathering around the modern wood table for a meal with fr

7. Theater • Game Room • Gym • Firepit • 4BR Home

Theater • Game Room • Gym • Firepit • 4BR Home
Belmont Cragin
10.0 out of 10, Exceptional, (7 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is AU$754
includes taxes & fees
10 Nov - 11 Nov
Theater • Game Room • Gym • Firepit • 4BR Home
A bunk bed with a ladder, a small table, a potted plant, and a window with blinds.

8. Vintage meets Modern 20 min from Chicago.

Vintage meets Modern 20 min from Chicago.
Calumet City
The price is AU$521
includes taxes & fees
10 Nov - 11 Nov
Vintage meets Modern 20 min from Chicago.
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

9. Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
7.8 out of 10, Good, (36 reviews)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
The price is AU$421
includes taxes & fees
16 Nov - 17 Nov
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A modern living room with a grey sofa, a wooden coffee table, a green sofa, and a large window with curtains.

10. Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Gam...

Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Gam...
Brookfield
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay at Crimson Manor. The property was super clean and well furnished, and kitchen was well-appointed. Stacey was a very responsive and attentive host. Even when we had difficulty getting into the garage, she had it resolved in 10 minutes. The basement game room is awesome - especially if you have a family! We recommend this property!"
United States
Steve H.
The price is AU$639
includes taxes & fees
15 Nov - 16 Nov
Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Gam...
A bedroom with a stone wall, a TV mounted on it, a bed with a white comforter, and a view of the outdoors through a window.

11. Beautifully furnished one bedroom loft located in Chicago's South side suburb

Beautifully furnished one bedroom loft located in Chicago's South side suburb
Hazel Green
10.0 out of 10, Exceptional, (1 review)
"Super great location, we had a concert at Tinley Park, then explored Chicago with a river cruise and Second City Everything was perfect and so eat to just chill, come and go as we pleased In a nice neighborhood and interior was furnished beautifully. Definitely worth the price !!"
United States
Nick L.
The price is AU$484
includes taxes & fees
10 Nov - 11 Nov
Beautifully furnished one bedroom loft located in Chicago's South side suburb
A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

12. Back Unit Patio, Balcony, Yard, Smart TVs, W/D

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
10.0 out of 10, Exceptional, (1 review)
"Happy with communication, comfort and location"
United States
Kelly K.
The price is AU$416
includes taxes & fees
1 Dec - 2 Dec
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

13. Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
Westmont
9.6 out of 10, Exceptional, (7 reviews)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
The price is AU$374
includes taxes & fees
11 Nov - 12 Nov
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A single-story house with a covered porch, a front door, and a small garden area.

14. Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Oak Park
10.0 out of 10, Exceptional, (4 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is AU$583
includes taxes & fees
10 Nov - 11 Nov
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
A garage with a white door, brick pillars, and a car parked inside.

15. Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking

Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking
Oak Park
The price is AU$523
includes taxes & fees
12 Nov - 13 Nov
Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

16. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (64 reviews)
"We had a wonderful stay"
United States
Anonymous traveller
The price is AU$509
includes taxes & fees
16 Nov - 17 Nov
LUXE 3 BR, 2 BA + Hot Tub
A modern living room with a sofa, coffee table, TV, and a staircase leading to an upper floor.

17. Spacious 5BR 2BA Berwyn Home

Spacious 5BR 2BA Berwyn Home
Berwyn
10.0 out of 10, Exceptional, (1 review)
"experience was good i loved it honestly "
United States
jamya w.
The price is AU$1,008
includes taxes & fees
14 Nov - 15 Nov
Spacious 5BR 2BA Berwyn Home
A modern building with a large dome and circular design, surrounded by a landscaped area with trees and a water body.

18. Premier 9BR Art Deco manor with garage.

Premier 9BR Art Deco manor with garage.
Lakeview
7.4 out of 10, Good, (3 reviews)
"Check in seamless, property was clean and very well appointed, and hosts were responsive, professional and polite. Can’t ask for much more. "
United States
Joel D.
The price is AU$2,514
includes taxes & fees
16 Nov - 17 Nov
Premier 9BR Art Deco manor with garage.
A cozy outdoor seating area with Adirondack chairs around a fire pit, string lights overhead, and a house in the background.

19. Firepit • Game Room • Theater • Gym • Sleeps 18

Firepit • Game Room • Theater • Gym • Sleeps 18
Austin
6.0 out of 10, (1 review)
"Ok place to fit large families if no other option available. Not suitable for kids with allergies as there are some opportunities in the cleanness and maintenance of the property.The communication were ok for reserving but very limited during the stay.The floor os severely damaged as well."
United States
Adrian Cesar C.
The price is AU$1,328
includes taxes & fees
10 Nov - 11 Nov
Firepit • Game Room • Theater • Gym • Sleeps 18
A modern living room with a grey sofa, a wooden coffee table, a green sofa, and a large window with curtains.

20. Vibrant House, Walk to Train, Game Room

Vibrant House, Walk to Train, Game Room
Brookfield
10.0 out of 10, Exceptional, (13 reviews)
"Wonderful place to stay!"
United States
Chasity D.
Vibrant House, Walk to Train, Game Room
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

Jaslin Hotel

Jaslin Hotel

10/10 Excellent
"Great!"
Stephanie 3-night trip
Posted less than an hour ago
Jaslin Hotel

Find out more about South Side

South Side Holiday Homes information

Number of reviews
237
Accommodation
86 Holiday Homes
Lowest Price
AU$291
Highest Price
AU$2,514

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