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Holiday Homes in Far Southwest Side

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Far Southwest Side holiday homes

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

1. 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, (35 reviews)
"I had a fun stay "
United States
Jusu K.
The price is €185
includes taxes & fees
4 Oct - 5 Oct
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

2. 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
9.4 out of 10, Exceptional, (3 reviews)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
The price is €201
includes taxes & fees
26 Oct - 27 Oct
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
Thoughtful design touches — from soft textures to greenery and mirrored accents — make this space feel both serene and sophisticated.

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)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is €508
includes taxes & fees
5 Oct - 6 Oct
Theater • Game Room • Gym • Firepit • 4BR Home
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.

4. 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 €350
includes taxes & fees
7 Oct - 8 Oct
Beautifully furnished one bedroom loft located in Chicago's South side suburb
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

5. 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, (34 reviews)
"Was a very nice stay and the host was very helpful and got very quick responses "
United States
Eduardo
The price is €275
includes taxes & fees
14 Oct - 15 Oct
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

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

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is €283
includes taxes & fees
26 Oct - 27 Oct
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
A marble countertop with a cheese platter, grapes, nuts, and a bottle of wine.

7. 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 €459
includes taxes & fees
6 Oct - 7 Oct
Game Room • Fire-pit • Playground • Gym • Billiard
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

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

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (9 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 €886
includes taxes & fees
5 Oct - 6 Oct
Sleeps 18 • 8BR • Game Room • Gym • Theater
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

9. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (63 reviews)
"We had a wonderful stay"
United States
Anonymous traveller
The price is €329
includes taxes & fees
6 Oct - 7 Oct
LUXE 3 BR, 2 BA + Hot Tub
A single-story house with a covered porch, a front door, and a small garden area.

10. 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 €312
includes taxes & fees
6 Oct - 7 Oct
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Room

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

Arcade • Theater • Gym • Office • Sleeps 15
Portage Park
9.0 out of 10, Wonderful, (4 reviews)
"Good place for a large group or family."
United States
Daniel J.
The price is €735
includes taxes & fees
4 Oct - 5 Oct
Arcade • Theater • Gym • Office • Sleeps 15
A bedroom with a bed, a nightstand, a wall-mounted lamp, and a plant.

12. Romantic Escape - Adult Playhouse with Exotic Dungeon

Romantic Escape - Adult Playhouse with Exotic Dungeon
South Holland
8.8 out of 10, Excellent, (13 reviews)
"enjoyed my stay cant wait to book again "
United States
Anonymous traveller
The price is €429
includes taxes & fees
4 Oct - 5 Oct
Romantic Escape - Adult Playhouse with Exotic Dungeon
A modern living room with a sectional sofa, a coffee table, and a TV.

13. 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 €206
includes taxes & fees
4 Oct - 5 Oct
Attractive Coach House Apartment for rent in Oak Park.
A living room with a brown sofa, a coffee table, and a patterned rug. There is a staircase leading to another room.

14. Spacious 3br home near Chicago, fenced yard for pets

Spacious 3br home near Chicago, fenced yard for pets
Richton Park
9.0 out of 10, Wonderful, (29 reviews)
"Very spacious accommodations in a very nice neighborhood. Convenient to food and shopping. Great value for the cost. "
United States
Greg S.
The price is €425
includes taxes & fees
7 Oct - 8 Oct
Spacious 3br home near Chicago, fenced yard for pets
A backyard with a barbecue grill, a dining table with chairs, and a fire pit.

15. PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Lisle
9.4 out of 10, Exceptional, (36 reviews)
"Clean house, Nice amenities, roomy and Close to the city! We very much enjoyed our stay here. "
United States
Ella A.
The price is €298
includes taxes & fees
4 Oct - 5 Oct
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
A cozy living room with a neon sign, a fireplace, a television, and a guitar.

16. 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, (44 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."
United States
Alison G.
The price is €922
includes taxes & fees
7 Oct - 8 Oct
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
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 €682
includes taxes & fees
17 Oct - 18 Oct
Spacious 5BR 2BA Berwyn Home
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

18. 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 €439
includes taxes & fees
14 Oct - 15 Oct
Classic Forest Park Foursquare < 1 Mi to Blue Line
A modern kitchen with dark wood cabinets, stainless steel appliances, a granite countertop, and a small island with stools.

19. Lockport Haven/3 King Beds/Wi-fi/Near Downtown!

Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
Lockport
10.0 out of 10, Exceptional, (15 reviews)
"Amazing property had everything we need! "
United States
Rachel
The price is €423
includes taxes & fees
4 Oct - 5 Oct
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
A modern living room with a grey sofa, a black coffee table, and a large window with a view of a house and greenery.

20. Entire home in Lockport, Illinois

Entire home in Lockport, Illinois
Lockport
8.8 out of 10, Excellent, (5 reviews)
"The house is very clean. The host was very kind and responsive. "
United States
Susan B.
The price is €401
includes taxes & fees
4 Oct - 5 Oct
Entire home in Lockport, Illinois
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 Far Southwest Side Hotel Reviews

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

8/10 Good
"Older hotel. Everything seemed tight (room, hallways, elevator. Sometimes it takes a while for valet since the drivers had to manage two hotels, averaging around 10-15min. The staff were very friendly though. Would I stay here again? Probably not."
Choua 2-night trip
Posted 6 hours ago
Hotel Saint Clair- Magnificent Mile

Find out more about Far Southwest Side

Far Southwest Side Holiday Homes information

Number of reviews
201
Accommodation
327 Holiday Homes
Lowest Price
€185
Highest Price
€922

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