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
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for South Side holiday homes

A living room with a sofa, two armchairs, a coffee table, a flat-screen TV, and a painting on the wall.

1. Designer 3BR Near Beach & Obama Center

Designer 3BR Near Beach & Obama Center
Woodlawn
The price is €696
includes taxes & fees
29 Sept - 30 Sept
Designer 3BR Near Beach & Obama Center
A residential area with two houses, one with a turret and another with a gabled roof.

2. Private Yard Near Beach & Obama Center

Private Yard Near Beach & Obama Center
Woodlawn
The price is €780
includes taxes & fees
29 Sept - 30 Sept
Private Yard Near Beach & Obama Center
A room with a bunk bed, a door, a flat-screen TV, and a window with curtains.

3. Designer Home | Steps to the Obama Center & Beach

Designer Home | Steps to the Obama Center & Beach
Woodlawn
The price is €958
includes taxes & fees
29 Sept - 30 Sept
Designer Home | Steps to the Obama Center & Beach
A billiards room with multiple tables, large windows, and a high ceiling with exposed ductwork.

4. Wabash 4BR - Pool, Free In & Out Parking 1

Wabash 4BR - Pool, Free In & Out Parking 1
Downtown Chicago
The price is €615
includes taxes & fees
8 Oct - 9 Oct
Wabash 4BR - Pool, Free In & Out Parking 1

5. 4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
Near North Side
9.4 out of 10, Exceptional, (22 reviews)
"Very clean, very quite loved having 3 bathrooms, had everything you’d need for your stay"
Canada
LM
The price is €746
includes taxes & fees
17 Sept - 18 Sept
4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
A wooden deck with a railing, a staircase, and a window with a wreath.

6. 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, (34 reviews)
"I had a fun stay "
United States
Jusu K.
The price is €181
includes taxes & fees
15 Sept - 16 Sept
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

7. Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
9.8 out of 10, Exceptional, (6 reviews)
The price is €897
includes taxes & fees
18 Sept - 19 Sept
Modern 3BR Apartment Near North Ave Shops
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

8. 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, (33 reviews)
"Pros: Quiet neighborhood, felt safe going in and out of the house. Upstairs bathroom shower was amazing. Cons: warmer in living room, stained pillows, couches and floors felt like dust mites all over( simple fix) All in all it was a good stay."
United States
Amal
The price is €268
includes taxes & fees
14 Sept - 15 Sept
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A living room with a sectional sofa, a round wooden coffee table, and three framed artworks on the wall.

9. 4BR Retreat w/ Theater, Arcade, Gym and Firepit

4BR Retreat w/ Theater, Arcade, Gym and Firepit
Belmont Cragin
10.0 out of 10, Exceptional, (6 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is €587
includes taxes & fees
21 Sept - 22 Sept
4BR Retreat w/ Theater, Arcade, Gym and Firepit
A modern living room with a sectional sofa, a coffee table, and a TV.

10. Attractive Coach House Apartment for rent in Oak Park.

Attractive Coach House Apartment for rent in Oak Park.
Oak Park
8.6 out of 10, Excellent, (4 reviews)
"The house was super clean , very quiet neighborhood !! Check in was super easy we enjoyed our stay"
United States
kerston b.
The price is €201
includes taxes & fees
22 Sept - 23 Sept
Attractive Coach House Apartment for rent in Oak Park.
A modern balcony with a city view, a cushioned chair, a small table with a plant, and a potted plant on the floor.

11. ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.4 out of 10, Exceptional, (29 reviews)
"Beautiful place and location! Had a great time with my family here"
United States
Pedro C.
ENVITAE Hotel, 4BR Luxury Modern Apartments
A marble countertop with a cheese platter, grapes, nuts, and a bottle of wine.

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

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful house. Lots of room and the games in the basement were awesome. Our grandsons loved them. The back yard is very nice too. The neighborhood is very nice. Everyone is so friendly. We had a great time."
United States
kim r.
The price is €515
includes taxes & fees
17 Sept - 18 Sept
Game Room • Fire-pit • Playground • Gym • Billiard
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

13. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (57 reviews)
"Hot tub was very nice!"
United States
Jeff
The price is €328
includes taxes & fees
14 Sept - 15 Sept
LUXE 3 BR, 2 BA + Hot Tub
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, (3 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is €307
includes taxes & fees
6 Oct - 7 Oct
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
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.

15. 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
The price is €291
includes taxes & fees
15 Sept - 16 Sept
Beautifully furnished one bedroom loft located in Chicago's South side suburb
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

16. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
Forest Park
10.0 out of 10, Exceptional, (2 reviews)
"Great location, great place to stay, host was friendly. Parking was great. Hoping to be able to stay again in the near future."
United States
LEM R.
The price is €429
includes taxes & fees
22 Sept - 23 Sept
Classic Forest Park Foursquare < 1 Mi to Blue Line

17. Arcade • Theater • Gym • Office • Sleeps 15

Arcade • Theater • Gym • Office • Sleeps 15
Portage Park
8.8 out of 10, Excellent, (3 reviews)
"Great home, clean ample space. Host was responsive and helpful. I would certainly stay again."
United States
Latasha C.
The price is €668
includes taxes & fees
22 Sept - 23 Sept
Arcade • Theater • Gym • Office • Sleeps 15
A modern kitchen with stainless steel appliances, wooden cabinets, and a tiled backsplash.

18. PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Westchester
9.4 out of 10, Exceptional, (23 reviews)
"Great location and the place was immaculate. Host was very nice."
United States
Carl M.
The price is €481
includes taxes & fees
22 Sept - 23 Sept
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
A white two-story house with a porch, steps, and a small table with chairs.

19. Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (33 reviews)
"Would stay there again"
United States
Margaret L.
The price is €542
includes taxes & fees
21 Sept - 22 Sept
Oak Park Victorian by FLW Studio
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

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

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (8 reviews)
"The house is beautiful with plenty of space, the park is right across the street, was able to host a birthday party with lots to keep the kids entertained and have space to eat and mingle, the rooms were comfortable and surprisingly large for how small the house looks from the outside. The host responded promptly and was accommodating. Would book and recommend to others!"
United States
Ashley Y.
The price is €925
includes taxes & fees
20 Sept - 21 Sept
Sleeps 18 • 8BR • Game Room • Gym • Theater
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

Sophy Hyde Park

Sophy Hyde Park

10/10 Excellent
"This is a “beautiful”"
Carol 4-night trip
Posted less than an hour ago
Sophy Hyde Park

Find out more about South Side

South Side Holiday Homes information

Number of reviews
169
Accommodation
92 Holiday Homes
Lowest Price
€181
Highest Price
€958

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