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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 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 ¥31,059
¥79,337 total
includes taxes & fees
Nov 15 - Nov 16
Spacious 3BR · Bronzeville/South Loop · Sleeps 8

2. South Loop · 3 Kings · Steps from McCormick Place

South Loop · 3 Kings · Steps from McCormick Place
Near South Side
9.0 out of 10, Wonderful, (10 reviews)
"Great space!"
United States
Kyle H.
South Loop · 3 Kings · Steps from McCormick Place

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)
"Quiet neighborhood, comfy beds, attentive hosts. Would stay again."
United States
Scott n Holly K.
The price is ¥22,863
¥31,513 total
includes taxes & fees
Nov 15 - Nov 16
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

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

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful night, boys loved the arcade area."
United States
Anonymous traveler
The price is ¥24,303
¥142,286 total
includes taxes & fees
Nov 17 - Nov 18
Sleeps 18 • 8BR • Game Room • Gym • Theater

5. Game Room • Fire-pit • Playground • Gym • Billiard

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
9.6 out of 10, Exceptional, (5 reviews)
"Everyone was super happy with the house and the location."
United States
Rhiannon
The price is ¥20,642
¥82,078 total
includes taxes & fees
Nov 16 - Nov 17
Game Room • Fire-pit • Playground • Gym • Billiard

6. 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)
"Great location. Great place to stay. "
United States
Jill L.
The price is ¥41,571
¥89,180 total
includes taxes & fees
Nov 15 - Nov 16
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops

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)
"We enjoyed our stay at Crimson Manor. The property was super clean and well furnished, and kitchen was well-appointed. Stacey was a very responsive and attentive host. Even when we had difficulty getting into the garage, she had it resolved in 10 minutes. The basement game room is awesome - especially if you have a family! We recommend this property!"
United States
Steve H.
The price is ¥24,943
¥69,653 total
includes taxes & fees
Nov 15 - Nov 16
Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Gam...

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 bed
Maywood
7.8 out of 10, Good, (36 reviews)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
The price is ¥23,726
¥46,065 total
includes taxes & fees
Nov 16 - Nov 17
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

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

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
10.0 out of 10, Exceptional, (1 review)
"Happy with communication, comfort and location"
United States
Kelly K.
The price is ¥20,345
¥46,114 total
includes taxes & fees
Dec 1 - Dec 2
Back Unit Patio, Balcony, Yard, Smart TVs, W/D

10. 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 ¥18,467
¥92,218 total
includes taxes & fees
Nov 16 - Nov 17
Theater • Game Room • Gym • Firepit • 4BR Home

11. 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 ¥39,144
¥53,499 total
includes taxes & fees
Nov 15 - Nov 16
Beautifully furnished one bedroom loft located in Chicago's South side suburb

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)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
The price is ¥27,161
¥41,147 total
includes taxes & fees
Nov 22 - Nov 23
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

13. Private Coach House in FLW District w/ Theater, Arcade & Kid-Friendly Yard

Private Coach House in FLW District w/ Theater, Arcade & Kid-Friendly Yard
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 ¥28,866
¥60,849 total
includes taxes & fees
Dec 7 - Dec 8
Private Coach House in FLW District w/ Theater, Arcade & Kid-Friendly Yard

14. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (65 reviews)
"It was a great home to stay at house was clean, some dirty sheets left on top of washer but other than that everything was good , will definitely come back"
United States
Brenda M
The price is ¥28,759
¥56,235 total
includes taxes & fees
Nov 16 - Nov 17
LUXE 3 BR, 2 BA + Hot Tub

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
Vintage meets Modern 20 min from Chicago.

16. Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking

Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking
Oak Park
The price is ¥27,161
¥58,348 total
includes taxes & fees
Nov 18 - Nov 19
Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking

17. Firepit • Game Room • Theater • Gym • Sleeps 18

Firepit • Game Room • Theater • Gym • Sleeps 18
Austin
6.0 out of 10, (1 review)
"Ok place to fit large families if no other option available. Not suitable for kids with allergies as there are some opportunities in the cleanness and maintenance of the property.The communication were ok for reserving but very limited during the stay.The floor os severely damaged as well."
United States
Adrian Cesar C.
The price is ¥27,321
¥148,399 total
includes taxes & fees
Nov 18 - Nov 19
Firepit • Game Room • Theater • Gym • Sleeps 18

18. 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 ¥41,344
¥95,070 total
includes taxes & fees
Dec 7 - Dec 8
Oak Park Victorian by FLW Studio

19. Premier 9BR Art Deco manor with garage.

Premier 9BR Art Deco manor with garage.
Lakeview
7.4 out of 10, Good, (3 reviews)
"Check in seamless, property was clean and very well appointed, and hosts were responsive, professional and polite. Can’t ask for much more. "
United States
Joel D.
The price is ¥83,416
¥292,334 total
includes taxes & fees
Dec 8 - Dec 9
Premier 9BR Art Deco manor with garage.

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)
"We had a great time at this property while our family explored Chicago. We found everything about the property was awesome for our family. Sitting outside with coffee in the morning was fantastic. Quiet neighborhood and very close to grocery store. We would stay there again. If we had to make any recommendations it would be that the living room could use more seating as we were five adults and had to use kitchen chairs for all to have a seat. I would also consider new sofa downstairs. It sits...
United States
Stephen K.
The price is ¥31,946
¥70,951 total
includes taxes & fees
Nov 18 - Nov 19
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
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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