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Holiday Homes in Southwest Side

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Southwest Side holiday homes

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

1. 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
Game Room • Fire-pit • Playground • Gym • Billiard
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)
"I had a fun stay "
United States
Jusu K.
The price is €179
includes taxes & fees
12 Nov - 13 Nov
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

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

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is €247
includes taxes & fees
9 Nov - 10 Nov
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

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)
"Wonderful night, boys loved the arcade area."
United States
Anonymous traveller
The price is €793
includes taxes & fees
9 Nov - 10 Nov
Sleeps 18 • 8BR • Game Room • Gym • Theater
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

5. 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 €481
includes taxes & fees
9 Nov - 10 Nov
Theater • Game Room • Gym • Firepit • 4BR Home
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

6. 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)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
The price is €237
includes taxes & fees
9 Nov - 10 Nov
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A modern bathroom with a large mirror, a sink, and two hanging planters with greenery.

7. 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.
4 BR • Theater Room • Gym • Walk to Lincoln Park!
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, (35 reviews)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
The price is €263
includes taxes & fees
16 Nov - 17 Nov
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A single-story house with a covered porch, a front door, and a small garden area.

9. 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 €395
includes taxes & fees
1 Dec - 2 Dec
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
A cozy living room with a neon sign, a fireplace, a television, and a guitar.

10. 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.
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
A modern living room with a grey sofa, a wooden coffee table, a green sofa, and a large window with curtains.

11. 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 €385
includes taxes & fees
9 Nov - 10 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.

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)
"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 €296
includes taxes & fees
16 Nov - 17 Nov
Beautifully furnished one bedroom loft located in Chicago's South side suburb
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.

13. 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)
"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...
United States
Denise G.
The price is €363
includes taxes & fees
18 Nov - 19 Nov
Cozy Home | King Bed | 10P | Metra |Chicago Suburb
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

14. 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 €322
includes taxes & fees
16 Nov - 17 Nov
LUXE 3 BR, 2 BA + Hot Tub
A modern living room with a dining area, a sofa set, and a television mounted on the wall.

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

Arcade • Theater • Gym • Office • Sleeps 15
Portage Park
9.2 out of 10, Wonderful, (5 reviews)
"Great home, clean ample space. Host was responsive and helpful. I would certainly stay again."
United States
Latasha C.
The price is €830
includes taxes & fees
8 Nov - 9 Nov
Arcade • Theater • Gym • Office • Sleeps 15
A dining room with a wooden table, black chairs, a red placemat, and a ceiling light fixture.

16. 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 €332
includes taxes & fees
16 Nov - 17 Nov
Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking
A cozy outdoor seating area with Adirondack chairs around a fire pit, string lights overhead, and a house in the background.

17. 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 €836
includes taxes & fees
16 Nov - 17 Nov
Firepit • Game Room • Theater • Gym • Sleeps 18
A modern living room with a sofa, coffee table, TV, and a staircase leading to an upper floor.

18. 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.
Spacious 5BR 2BA Berwyn Home
A modern living room with a grey sofa, a wooden coffee table, a green sofa, and a large window with curtains.

19. Vibrant House, Walk to Train, Game Room

Vibrant House, Walk to Train, Game Room
Brookfield
10.0 out of 10, Exceptional, (12 reviews)
"Wonderful place to stay!"
United States
Chasity D.
Vibrant House, Walk to Train, Game Room
A modern kitchen with stainless steel appliances, wooden cabinets, and a tiled backsplash.

20. 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)
"Great location and the place was immaculate. Host was very nice."
United States
Carl M.
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
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 Southwest Side Hotel Reviews

The Wade

The Wade

8/10 Good
"Very nice and comfortable"
Samantha 2-night trip
Posted 1 hour ago
The Wade

Find out more about Southwest Side

Southwest Side Holiday Homes information

Number of reviews
205
Accommodation
345 Holiday Homes
Lowest Price
€179
Highest Price
€836

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