South Side Holiday Homes from €187: Search Top House Rentals

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Our top choices for South Side holiday homes

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

A living room with a dark wood floor, a black sofa, a round coffee table, and a black cabinet with a mirror.

A kitchen with a built-in counter, pendant lights, and decorative wall art.

A modern kitchen with white cabinets, a granite countertop, a coffee machine, and a window with blinds.

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)

9.0/10

Wonderful

(2 reviews)

"This VRBO was perfect for our group! There was more than enough space. The host let us drop our luggage off early since we arrived in the area before 4. The listing initially had errors, but the host updated the listing and we knew what to expect coming into it. Thank you for a wonderful stay!"

Jamiee B.

The price is €635

€635

includes taxes & fees

1 Nov - 2 Nov

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

A wooden deck with a railing, a staircase, and a window with a wreath.

A dining table with a decorative runner, candles, and a framed picture.

A dining area with a round table, chairs, a decorative vase, and a patterned rug.

A two-story house with a porch, a small tree, and a sign that reads 'Ashlin House.'

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)

9.8/10

Exceptional

(37 reviews)

"I had a fun stay "

Jusu K.

The price is €187

€187

includes taxes & fees

1 Nov - 2 Nov

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

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

✔️ Toaster, blender, mixer, Crockpot, ice maker, electric water heater

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

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

Belmont Cragin

10.0 out of 10, Exceptional, (7 reviews)

10/10

Exceptional

(7 reviews)

"Great location, safe and quiet. Perfect for our family of 6!"

Jason

The price is €503

€503

includes taxes & fees

2 Nov - 3 Nov

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

A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

A bedroom with a bed, a dresser, a TV on the wall, and a door leading to a bathroom.

A white arched cabinet with glass doors, containing kitchen appliances like a blender, toaster, and kettle.

A modern living room with a white sofa, a round coffee table, a fireplace, and a flat-screen TV mounted on the wall.

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

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

Portage Park

10.0 out of 10, Exceptional, (10 reviews)

10/10

Exceptional

(10 reviews)

"Wonderful night, boys loved the arcade area."

Anonymous traveller

The price is €834

€834

includes taxes & fees

2 Nov - 3 Nov

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

A modern living room with a dining area, a sofa set, and a television mounted on the wall.

A modern living room with a sofa, a coffee table, and a television mounted on the wall.

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

Arcade • Theater • Gym • Office • Sleeps 15

Portage Park

9.0 out of 10, Wonderful, (4 reviews)

9.0/10

Wonderful

(4 reviews)

"Good place for a large group or family."

Daniel J.

The price is €717

€717

includes taxes & fees

1 Nov - 2 Nov

Arcade • Theater • Gym • Office • Sleeps 15

A modern living room with a grey sofa, a wooden coffee table, a green sofa, and a large window with curtains.

A dining area with a round table, blue velvet chairs, and a gold chandelier.

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

A modern living room with a sofa, coffee table, and a dining area with blue chairs.

6. Vibrant House, Walk to Train, Game Room

Vibrant House, Walk to Train, Game Room

Brookfield

10.0 out of 10, Exceptional, (12 reviews)

10/10

Exceptional

(12 reviews)

"Wonderful place to stay!"

Chasity D.

The price is €632

€632

includes taxes & fees

9 Nov - 10 Nov

Vibrant House, Walk to Train, Game Room

A covered patio with a hammock, a barbecue grill, and a dining area with a table and chairs.

A modern living room with a sofa, coffee table, and large windows.

A modern hallway with a glass door, a round mirror, a wooden bench, and a cactus plant.

A modern kitchen with a central island, built-in appliances, and a dining area with a view.

7. Chicago Riverhouse with private fenced in oasis

Chicago Riverhouse with private fenced in oasis

North Park

10.0 out of 10, Exceptional, (45 reviews)

10/10

Exceptional

(45 reviews)

"House was perfect for our needs and all as described per the listing."

Robert S.

The price is €522

€522

includes taxes & fees

1 Nov - 2 Nov

Chicago Riverhouse with private fenced in oasis

A cozy living room with a neon sign, a fireplace, a television, and a guitar.

A cozy interior with a neon sign reading "The Village Inn," brick walls, a marble table, and comfortable seating.

A spacious living area with a sofa, a dining table, and a kitchen in the background.

A covered outdoor area with wooden flooring, a green bench, a small table, and a potted plant.

8. 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)

9.6/10

Exceptional

(45 reviews)

"Location was great, beds were comfortable, overall the apartment was well appointed. Unfortunately there was a strong musty smell, mainly in the common areas. We opened the windows and tried running the AC, but couldn’t get rid of it. We did report it to our host, who was going to check it out following our departure."

Alison G.

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

A marble countertop with a cheese platter, grapes, nuts, and a bottle of wine.

A modern living room with a white sofa, a white armchair, and a floor lamp.

A modern kitchen with white cabinetry, a central island with bar stools, stainless steel appliances, and pendant lighting.

A modern living room with a fireplace, two white sofas, a coffee table, and a pool table.

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

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

Belmont Cragin

9.6 out of 10, Exceptional, (5 reviews)

9.6/10

Exceptional

(5 reviews)

"Everyone was super happy with the house and the location."

Rhiannon

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

A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

A single-story house with a front porch, a staircase leading to the entrance, and a driveway.

A living room with a brown sofa, a beige ottoman, and a red vase. There are three framed pictures on the wall and a window with blinds.

A spacious living room with a large sectional sofa, a coffee table, and a kitchen area with a refrigerator and cabinets.

10. 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, (35 reviews)

7.8/10

Good

(35 reviews)

"Very nice home with basement bar. Host was very accommodating."

Carl T.

The price is €277

€277

includes taxes & fees

2 Nov - 3 Nov

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

A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

A modern kitchen with a dining area, a bar stool, and a decorative wall piece.

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

A single-story house with a front door, two windows, and a small porch.

11. 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, (5 reviews)

9.6/10

Exceptional

(5 reviews)

"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."

Tomas R.

The price is €250

€250

includes taxes & fees

9 Nov - 10 Nov

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

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.

A living room with a sofa, a coffee table, a lamp, a globe, and a TV mounted on the wall.

12. 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)

10/10

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 !!"

Nick L.

The price is €308

€308

includes taxes & fees

1 Nov - 2 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.

A kitchen with wooden cabinets, a stainless steel stove, a microwave, and a refrigerator.

A laundry room with a front-loading washing machine, a dryer, and a small sink.

A living room with a black leather sofa, two blue armchairs, a coffee table, and a floral rug.

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

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

Westmont

The price is €242

€242

includes taxes & fees

2 Nov - 3 Nov

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

A dining room with a wooden table, black chairs, a red placemat, and a ceiling light fixture.

A courtyard with a picnic table and benches, surrounded by brick buildings with multiple windows.

A living room with a flat-screen TV, a blue sofa, a wooden coffee table, and a dining area with a table and chairs.

A kitchen with white cabinets, a black refrigerator, a microwave, a stove, and a window with a view.

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

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

Oak Park

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

A single-story house with a covered porch, a front door, and a small garden area.

A bedroom with a bed, a nightstand, a lamp, and a door.

A kitchen with a coffee maker, a stove, and a window.

A staircase leading to a porch with a 'WELCOME' sign.

15. 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)

10/10

Exceptional

(4 reviews)

"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."

Willow M.

The price is €352

€352

includes taxes & fees

3 Nov - 4 Nov

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

A hot tub with water, a wooden deck, and a chair.

A compact kitchen with wooden cabinets, a white refrigerator, a stove, and a dining area with a table and chairs.

A living room with a fireplace, leather sofas, a flat-screen TV, and a lamp.

16. Charming 1-bedroom apt in house by creek with AC, in delightful Portage

Charming 1-bedroom apt in house by creek with AC, in delightful Portage

Portage

9.8 out of 10, Exceptional, (11 reviews)

9.8/10

Exceptional

(11 reviews)

"Nice place close to the beach."

Zdenek M.

The price is €240

€240

includes taxes & fees

30 Nov - 1 Dec

Charming 1-bedroom apt in house by creek with AC, in delightful Portage

A modern kitchen with stainless steel appliances, wooden cabinets, and a tiled backsplash.

An outdoor deck with a brick fireplace and a grill.

A bedroom with a checkered bedspread, a tufted headboard, and a door with a white frame.

A living room with a brick fireplace, a black leather sofa, a round ottoman, and a flat-screen TV mounted on the wall.

17. 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

9.6 out of 10, Exceptional, (25 reviews)

9.6/10

Exceptional

(25 reviews)

"Great place Great location "

Josh W.

The price is €344

€344

includes taxes & fees

2 Nov - 3 Nov

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

A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

A living room with a glass coffee table, a potted plant, a flat-screen TV, a dining table with chairs, and a clock on the wall.

A living room with a glass coffee table, a gray sofa, and a patterned rug.

A modern kitchen with dark wooden cabinets, a white stove, a microwave, and a sink.

18. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub

Elmhurst

8.6 out of 10, Excellent, (64 reviews)

8.6/10

Excellent

(64 reviews)

"We had a wonderful stay"

Anonymous traveller

LUXE 3 BR, 2 BA + Hot Tub

A modern living room with a grey sofa, a white armchair, a coffee table, and a TV. There is a kitchen area in the background with a dining table and chairs.

A backyard patio with wicker furniture, a barbecue grill, and string lights.

A bedroom with a large bed, two bedside tables, a wall-mounted artwork, and a window with curtains.

A modern kitchen with stainless steel appliances, a dining area with blue tableware, and a cityscape painting on the wall.

19. Cozy Home | King Bed | 10P | Metra |Chicago Suburb

Cozy Home | King Bed | 10P | Metra |Chicago Suburb

Highland Hills

9.4 out of 10, Exceptional, (3 reviews)

9.4/10

Exceptional

(3 reviews)

"I booked this property because I was told (before I made the reservation) that the bedroom and one of the bathrooms were on the main floor. I specifically inquired whether my mother-in-law would need to use stairs to access a bedroom and bathroom. In the words of the host, "the main living area, kitchen, two bedrooms and a full bathroom are on the main floor. Only the basement requires the use of steps ". This was not the case. The two bedrooms and a full bathroom are up a flight of 5...

Denise G.

The price is €354

€354

includes taxes & fees

18 Nov - 19 Nov

Cozy Home | King Bed | 10P | Metra |Chicago Suburb

A modern building with a large dome and circular design, surrounded by a landscaped area with trees and a water body.

A dining area with a glass table and black chairs with gold trim, a chandelier, and a view of the street through large windows.

A modern kitchen with stainless steel appliances, a built-in oven, and a dining area with bar stools.

A bedroom with a bed, bedside table, desk, and a window with curtains.

20. Premier 9BR Art Deco manor with garage.

Premier 9BR Art Deco manor with garage.

Lakeview

7.4 out of 10, Good, (3 reviews)

7.4/10

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. "

Joel D.

The price is €1,660

€1,660

includes taxes & fees

2 Nov - 3 Nov

Premier 9BR Art Deco manor with garage.

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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"Secure parking"

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10/10 Excellent

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South Side Holiday Homes information

Number of reviews	261
Accommodation	92 Holiday Homes
Lowest Price	€187
Highest Price	€1,660

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Holiday Homes in South Side

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for South Side holiday homes

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

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

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

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

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

6. Vibrant House, Walk to Train, Game Room

7. Chicago Riverhouse with private fenced in oasis

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

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

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

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

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

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

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

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

16. Charming 1-bedroom apt in house by creek with AC, in delightful Portage

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

18. LUXE 3 BR, 2 BA + Hot Tub

19. Cozy Home | King Bed | 10P | Metra |Chicago Suburb

20. Premier 9BR Art Deco manor with garage.

Find holiday rentals that suit your style

Top South Side Hotel Reviews

SpringHill Suites by Marriott Chicago Chinatown

Find out more about South Side

South Side Holiday Homes information

Explore a world of travel with Expedia