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Holiday Homes in Southwest Side

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Southwest Side holiday homes

A modern living room with a sofa, armchairs, a coffee table, a TV, and a large window with curtains.

1. Spacious 3BR · Bronzeville/South Loop · Sleeps 8

Spacious 3BR · Bronzeville/South Loop · Sleeps 8
Near South Side
9.0 out of 10, Wonderful, (6 reviews)
"Excellent stay! The property was clean and an easy walk to McCormick Place convention center. The space was colossal and well appointed, with soap and towels provided for the shower. We were greeted by a wonderful gentleman who took the time to explain the Chicago area to us. Checkout was a breeze—just had to leave our keys—and the instructions were very clear. There was only minimal housekeeping required before leaving the apartment. I would definitely stay here again"
United States
Ilir T.
The price is NZ$717
includes taxes & fees
29 Sept - 30 Sept
Spacious 3BR · Bronzeville/South Loop · Sleeps 8

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

Theater • Game Room • Gym • Firepit • 4BR Home
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 NZ$950
includes taxes & fees
28 Sept - 29 Sept
Theater • Game Room • Gym • Firepit • 4BR Home

3. Cozy Studio Suite, Steps from River North & Shops

Cozy Studio Suite, Steps from River North & Shops
Near North Side
9.4 out of 10, Exceptional, (3 reviews)
"Clean apartment in cozy neighborhood"
United States
Susannah R.
Cozy Studio Suite, Steps from River North & Shops
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

4. 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 NZ$536
includes taxes & fees
28 Sept - 29 Sept
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

5. 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 NZ$856
includes taxes & fees
28 Sept - 29 Sept
Classic Forest Park Foursquare < 1 Mi to Blue Line
A modern living room with a sectional sofa, a coffee table, and a TV.

6. 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 NZ$404
includes taxes & fees
6 Oct - 7 Oct
Attractive Coach House Apartment for rent in Oak Park.
A white two-story house with a porch, steps, and a small table with chairs.

7. 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 NZ$980
includes taxes & fees
29 Sept - 30 Sept
Oak Park Victorian by FLW Studio
A single-story house with a covered porch, a front door, and a small garden area.

8. 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 NZ$596
includes taxes & fees
6 Oct - 7 Oct
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
A wooden deck with a railing, a staircase, and a window with a wreath.

9. 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 NZ$362
includes taxes & fees
4 Oct - 5 Oct
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

10. 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 NZ$1,258
includes taxes & fees
30 Sept - 1 Oct
Arcade • Theater • Gym • Office • Sleeps 15
A living room with a flat-screen TV mounted on the wall, a plant on a stand, and a window with blinds.

11. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!
Lincoln Park
The price is NZ$1,183
includes taxes & fees
29 Sept - 30 Sept
4 BR • Theater Room • Gym • Walk to Lincoln Park!
A modern kitchen with stainless steel appliances, wooden cabinets, and a tiled backsplash.

12. 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 NZ$769
includes taxes & fees
29 Sept - 30 Sept
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.

13. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (62 reviews)
"We had a wonderful stay"
United States
Anonymous traveller
The price is NZ$644
includes taxes & fees
28 Sept - 29 Sept
LUXE 3 BR, 2 BA + Hot Tub
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

14. 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 NZ$378
includes taxes & fees
25 Oct - 26 Oct
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A marble countertop with a cheese platter, grapes, nuts, and a bottle of wine.

15. 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 NZ$1,095
includes taxes & fees
1 Oct - 2 Oct
Game Room • Fire-pit • Playground • Gym • Billiard
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.

16. 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 NZ$688
includes taxes & fees
1 Oct - 2 Oct
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.

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

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is NZ$532
includes taxes & fees
5 Oct - 6 Oct
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
A two-story house with a garage, solar panels, and a red car parked in front.

18. Lombard 1BR & 1BH Suite Close to freeway & Mall

Lombard 1BR & 1BH Suite Close to freeway & Mall
Lombard
The price is NZ$674
includes taxes & fees
4 Oct - 5 Oct
Lombard 1BR & 1BH Suite Close to freeway & Mall
A modern living room with a grey sofa, a wooden coffee table, a green sofa, and a large window with curtains.

19. 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 NZ$1,406
includes taxes & fees
29 Sept - 30 Sept
Sleeps 10 + Coffee bar + Game Room + Train to CHGO - Holiday Home
A beach with people sunbathing and swimming, a lighthouse, and a pier extending into the water.

20. 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 NZ$1,529
includes taxes & fees
5 Oct - 6 Oct
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
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

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

10/10 Excellent
"This is such a great value, in such a great area. The front desk had great suggestions and helped us with our Chicago Transit day pass. We saved so much by just riding public transit. The room was clean, nice temperature control, perfect for a couple! Such nice staff. Safe area!"
Dawn 2-night trip
Posted less than an hour ago
Hotel Saint Clair- Magnificent Mile

Find out more about Southwest Side

Southwest Side Holiday Homes information

Number of reviews
408
Accommodation
357 Holiday Homes
Lowest Price
NZ$362
Highest Price
NZ$1,529

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