
Holiday Homes in Southwest Side
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Our top choices for Southwest Side holiday homes

1. Sleeps 18 • 8BR • Game Room • Gym • Theater
Sleeps 18 • 8BR • Game Room • Gym • TheaterPortage Park
10.0 out of 10, Exceptional, (10 reviews)
The price is NZ$1,574
includes taxes & fees
17 Nov - 18 Nov

2. Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Back Unit Patio, Balcony, Yard, Smart TVs, W/DWestmont
10.0 out of 10, Exceptional, (1 review)
The price is NZ$505
includes taxes & fees
1 Dec - 2 Dec

3. 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)
The price is NZ$348
includes taxes & fees
13 Nov - 14 Nov

4. 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, (7 reviews)
The price is NZ$456
includes taxes & fees
12 Nov - 13 Nov

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 bedMaywood
7.8 out of 10, Good, (36 reviews)
The price is NZ$512
includes taxes & fees
16 Nov - 17 Nov

6. 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)
The price is NZ$764
includes taxes & fees
15 Nov - 16 Nov

7. Game Room • Fire-pit • Playground • Gym • Billiard
Game Room • Fire-pit • Playground • Gym • BilliardBelmont Cragin
9.6 out of 10, Exceptional, (5 reviews)
The price is NZ$893
includes taxes & fees
17 Nov - 18 Nov

8. Private Coach House in FLW District w/ Theater, Arcade & Kid-Friendly Yard
Private Coach House in FLW District w/ Theater, Arcade & Kid-Friendly YardOak Park
10.0 out of 10, Exceptional, (4 reviews)
The price is NZ$726
includes taxes & fees
1 Dec - 2 Dec

9. Theater • Game Room • Gym • Firepit • 4BR Home
Theater • Game Room • Gym • Firepit • 4BR HomeBelmont Cragin
10.0 out of 10, Exceptional, (7 reviews)
The price is NZ$958
includes taxes & fees
12 Nov - 13 Nov

10. Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
Lincoln Park Cozy 3bd Home near Zoo | Lake | ShopsLincoln Park
9.6 out of 10, Exceptional, (45 reviews)
The price is NZ$993
includes taxes & fees
15 Nov - 16 Nov

11. LUXE 3 BR, 2 BA + Hot Tub
LUXE 3 BR, 2 BA + Hot TubElmhurst
8.6 out of 10, Excellent, (65 reviews)
The price is NZ$620
includes taxes & fees
16 Nov - 17 Nov

12. Beautifully furnished one bedroom loft located in Chicago's South side suburb
Beautifully furnished one bedroom loft located in Chicago's South side suburbHazel Green
10.0 out of 10, Exceptional, (1 review)
The price is NZ$595
includes taxes & fees
12 Nov - 13 Nov

13. Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking
Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage ParkingOak Park
The price is NZ$647
includes taxes & fees
12 Nov - 13 Nov

14. Cozy Home | King Bed | 10P | Metra |Chicago Suburb
Cozy Home | King Bed | 10P | Metra |Chicago SuburbHighland Hills
9.4 out of 10, Exceptional, (3 reviews)
The price is NZ$717
includes taxes & fees
18 Nov - 19 Nov

15. Oak Park Victorian by FLW Studio
Oak Park Victorian by FLW StudioOak Park
10.0 out of 10, Exceptional, (33 reviews)
The price is NZ$941
includes taxes & fees
10 Dec - 11 Dec

16. Firepit • Game Room • Theater • Gym • Sleeps 18
Firepit • Game Room • Theater • Gym • Sleeps 18Austin
6.0 out of 10, (1 review)
The price is NZ$1,635
includes taxes & fees
12 Nov - 13 Nov

17. Classic Forest Park Foursquare < 1 Mi to Blue Line
Classic Forest Park Foursquare < 1 Mi to Blue LineForest Park
10.0 out of 10, Exceptional, (2 reviews)
The price is NZ$809
includes taxes & fees
16 Nov - 17 Nov

18. 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)
The price is NZ$797
includes taxes & fees
18 Nov - 19 Nov

19. PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North CentralLisle
9.4 out of 10, Exceptional, (36 reviews)
The price is NZ$558
includes taxes & fees
12 Nov - 13 Nov

20. Vibrant House, Walk to Train, Game Room
Vibrant House, Walk to Train, Game RoomBrookfield
10.0 out of 10, Exceptional, (13 reviews)
The price is NZ$1,206
includes taxes & fees
16 Nov - 17 Nov
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 Chicago Hotel Collection - Magnificent Mile
10/10 Excellent
Find out more about Southwest Side
Southwest Side Holiday Homes information
Number of reviews | 286 |
|---|---|
Accommodation | 357 Holiday Homes |
Lowest Price | NZ$348 |
Highest Price | NZ$1,635 |
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- Pet-Friendly Holiday Packages Far Southwest Side
- Hyde Park Hair Salon
- Robie House
- Supreme Life Building
- Zhou B Art Center
- Visit Gage Park
- Visit Ashburn
- Visit Fuller Park
- Visit McKinley Park
- Visit Chicago Lawn
- Visit Washington Park
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- Visit Douglas



































































