Default HTG hotel image

Holiday Homes in Far Southwest Side

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 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 AU$302
includes taxes & fees
12 Oct - 13 Oct
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
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.

2. 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$487
includes taxes & fees
12 Oct - 13 Oct
Beautifully furnished one bedroom loft located in Chicago's South side suburb
A bedroom with a bed, a nightstand, a wall-mounted lamp, and a plant.

3. 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 AU$666
includes taxes & fees
12 Oct - 13 Oct
Romantic Escape - Adult Playhouse with Exotic Dungeon
A cozy living room with a neon sign, a fireplace, a television, and a guitar.

4. 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)
"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 AU$1,249
includes taxes & fees
12 Oct - 13 Oct
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
A modern living room with a sectional sofa, a coffee table, and a TV.

5. 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 AU$340
includes taxes & fees
13 Oct - 14 Oct
Attractive Coach House Apartment for rent in Oak Park.
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

6. 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)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
The price is AU$431
includes taxes & fees
13 Oct - 14 Oct
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.

7. Sleeps 10 + Coffee bar + Game Room + Train to CHGO - Holiday Home

Sleeps 10 + Coffee bar + Game Room + Train to CHGO - Holiday Home
Brookfield
10.0 out of 10, Exceptional, (12 reviews)
"Wonderful place to stay!"
United States
Chasity D.
The price is AU$1,042
includes taxes & fees
2 Nov - 3 Nov
Sleeps 10 + Coffee bar + Game Room + Train to CHGO - Holiday Home
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

8. 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$528
includes taxes & fees
13 Oct - 14 Oct
LUXE 3 BR, 2 BA + Hot Tub
Thoughtful design touches — from soft textures to greenery and mirrored accents — make this space feel both serene and sophisticated.

9. 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$911
includes taxes & fees
12 Oct - 13 Oct
Theater • Game Room • Gym • Firepit • 4BR Home
A beach with people sunbathing and swimming, a lighthouse, and a pier extending into the water.

10. Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Lincoln Park
9.8 out of 10, Exceptional, (193 reviews)
"Awesome house for family events. Great neighborhood and gathering space was great"
United States
Ann V.
The price is AU$1,436
includes taxes & fees
13 Oct - 14 Oct
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

11. 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 AU$680
includes taxes & fees
18 Oct - 19 Oct
Classic Forest Park Foursquare < 1 Mi to Blue Line
A modern kitchen with a marble countertop, wooden dining table, and yellow chairs.

12. Swanky Rooftop, Birthday, Anniversary sleeps 16

Swanky Rooftop, Birthday, Anniversary sleeps 16
Forest Park
10.0 out of 10, Exceptional, (4 reviews)
"Great property and location. Good for an extended group work stay. Highly recommended."
United States
Ken Y.
The price is AU$3,694
includes taxes & fees
12 Oct - 13 Oct
Swanky Rooftop, Birthday, Anniversary sleeps 16
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

13. 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 AU$1,429
includes taxes & fees
13 Oct - 14 Oct
Sleeps 18 • 8BR • Game Room • Gym • Theater
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$518
includes taxes & fees
29 Oct - 30 Oct
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
A modern kitchen with stainless steel appliances, wooden cabinets, and a tiled backsplash.

15. 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, (24 reviews)
"Great place Great location "
United States
Josh W.
The price is AU$764
includes taxes & fees
14 Oct - 15 Oct
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
A dining area with a black table set for four, surrounded by chairs. A vase with dried flowers and a candle holder are on the table.

16. 3-bedroom house in lovely Matteson with cool AC breeze

3-bedroom house in lovely Matteson with cool AC breeze
Matteson
10.0 out of 10, Exceptional, (1 review)
"clean, comfortable, hosts very responsive to communications, neighborhood felt safe, perfect location for our stay to attend sectionals NTRP tennis tournament at HF Racquet and Fitness Club"
United States
Susan H.
The price is AU$919
includes taxes & fees
12 Oct - 13 Oct
3-bedroom house in lovely Matteson with cool AC breeze
A living room with a brown sofa, a coffee table, and a patterned rug. There is a staircase leading to another room.

17. 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 AU$671
includes taxes & fees
12 Oct - 13 Oct
Spacious 3br home near Chicago, fenced yard for pets
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

18. 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 AU$351
includes taxes & fees
25 Oct - 26 Oct
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A spacious bedroom with a large bed, a desk, and a chair.

19. Westchester House | Sleeps 10 | Near Chicago & Parks | Close to Restaurants & Easy Local Transport Access | Long private driveway

Westchester House | Sleeps 10 | Near Chicago & Parks | Close to Restaurants & Easy Local Transport Access | Long private driveway
Westchester
10.0 out of 10, Exceptional, (1 review)
"Cute house with easy access to shopping and interstate"
United States
Jenny W.
The price is AU$1,167
includes taxes & fees
12 Oct - 13 Oct
Westchester House | Sleeps 10 | Near Chicago & Parks | Close to Restaurants & Easy Local Transport Access | Long private driveway
Casino

20. 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 AU$1,151
includes taxes & fees
11 Oct - 12 Oct
Arcade • Theater • Gym • Office • Sleeps 15
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Far Southwest Side Hotel Reviews

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"Lovely 1 night stay at the Michigan Ave Intercontinental Hotel. Very convenient with Valet Parking now right on Michigan Ave in front of the property! Rooms were comfortable and updated. Friendly staff and allowed us to check in before noon! Don't love the amenity fee for a 1 night stay when we used nothing....but it is what it is."
Brenda 1-night trip
Posted less than an hour ago
InterContinental Chicago Magnificent Mile by IHG

Find out more about Far Southwest Side

Far Southwest Side Holiday Homes information

Number of reviews
424
Accommodation
327 Holiday Homes
Lowest Price
AU$302
Highest Price
AU$3,694

Explore a world of travel with Expedia