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Our top choices for South Side vacation homes

1. Spacious 3BR · Bronzeville/South Loop · Sleeps 8
Spacious 3BR · Bronzeville/South Loop · Sleeps 8Near South Side
9.0 out of 10, Wonderful, (6 reviews)
The price is ¥31,059
¥79,337 total
includes taxes & fees
Nov 15 - Nov 16

2. South Loop · 3 Kings · Steps from McCormick Place
South Loop · 3 Kings · Steps from McCormick PlaceNear South Side
9.0 out of 10, Wonderful, (10 reviews)

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 ¥22,863
¥31,513 total
includes taxes & fees
Nov 15 - Nov 16

4. 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 ¥24,303
¥142,286 total
includes taxes & fees
Nov 17 - Nov 18

5. 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 ¥20,642
¥82,078 total
includes taxes & fees
Nov 16 - Nov 17

6. 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 ¥41,571
¥89,180 total
includes taxes & fees
Nov 15 - Nov 16

7. 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 ¥24,943
¥69,653 total
includes taxes & fees
Nov 15 - Nov 16

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 bedMaywood
7.8 out of 10, Good, (36 reviews)
The price is ¥23,726
¥46,065 total
includes taxes & fees
Nov 16 - Nov 17

9. 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 ¥20,345
¥46,114 total
includes taxes & fees
Dec 1 - Dec 2

10. 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 ¥18,467
¥92,218 total
includes taxes & fees
Nov 16 - Nov 17

11. 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 ¥39,144
¥53,499 total
includes taxes & fees
Nov 15 - Nov 16

12. 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 ¥27,161
¥41,147 total
includes taxes & fees
Nov 22 - Nov 23

13. 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 ¥28,866
¥60,849 total
includes taxes & fees
Dec 7 - Dec 8

14. 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 ¥28,759
¥56,235 total
includes taxes & fees
Nov 16 - Nov 17

15. Vintage meets Modern 20 min from Chicago.
Vintage meets Modern 20 min from Chicago.Calumet City
The price is ¥23,007
¥54,694 total
includes taxes & fees
Nov 15 - Nov 16

16. 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 ¥27,161
¥58,348 total
includes taxes & fees
Nov 18 - Nov 19

17. Firepit • Game Room • Theater • Gym • Sleeps 18
Firepit • Game Room • Theater • Gym • Sleeps 18Austin
6.0 out of 10, (1 review)
The price is ¥27,321
¥148,399 total
includes taxes & fees
Nov 18 - Nov 19

18. Oak Park Victorian by FLW Studio
Oak Park Victorian by FLW StudioOak Park
10.0 out of 10, Exceptional, (33 reviews)
The price is ¥41,344
¥95,070 total
includes taxes & fees
Dec 7 - Dec 8

19. Premier 9BR Art Deco manor with garage.
Premier 9BR Art Deco manor with garage.Lakeview
7.4 out of 10, Good, (3 reviews)
The price is ¥83,416
¥292,334 total
includes taxes & fees
Dec 8 - Dec 9

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)
The price is ¥31,946
¥70,951 total
includes taxes & fees
Nov 18 - Nov 19
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 reviews in South Side

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