South Side Holiday Homes
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Check availability on Holiday Homes in South Side
Featured Holiday Homes in South Side
LakeHouse
Chicago IL
During your stay at this holiday home, you're just a quick walk from Lake Michigan. Features include laundry facilities. Free WiFi and in-room jetted baths are available in the holiday home.
Küche
Waschmaschine
Lux Home in Chicago 7mins Downtown
Chicago IL
During your stay at this holiday home, you'll be within walking distance of Lake Michigan. A gym and laundry facilities are available. Enjoy your stay with amenities like a kitchen and 3.5 bathrooms in the holiday home.
Küche
Waschmaschine
Stay, Relax & Explore Chicago
Chicago IL
During your stay at this holiday home, you'll be close to University of Chicago. Features include laundry facilities. The holiday home includes amenities such as free WiFi and a TV.
Bronzeville Jazz Room. Beautiful, cozy, centered, relaxing, rustic.
Chicago IL
During your stay at this holiday home, you'll be within walking distance of Lake Michigan. Features include laundry facilities. Free WiFi and a kitchen are available in the holiday home.
Küche
Waschmaschine
Charming house in amazing Chicago with WiFi and AC. Close to many restaurants.
Chicago IL
During your stay at this holiday home, you'll be close to University of Chicago. Enjoy features like laundry facilities and an arcade/games room. The holiday home offers free WiFi and a kitchen.
Küche
Waschmaschine
1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown
Chicago IL
During your stay at this holiday home, you're just a quick walk from State Street. Enjoy features like laundry facilities. Free WiFi and a kitchen are available in the holiday home.
A Home Away From Home!
Chicago IL
During your stay at this holiday home, you'll be close to Horseshoe Hammond Casino. Features include laundry facilities. The holiday home offers 3 bathrooms and a fireplace.
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!
Chicago IL
During your stay at this holiday home, you'll be close to University of Chicago. You'll find features such as free WiFi in public areas and laundry facilities. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.
Küche
Waschmaschine
Cheerful 4 bedroom smart home w/ indoor fireplace
Chicago IL
During your stay at this holiday home, you'll be within walking distance of State Street. You'll find features such as laundry facilities. A kitchen and 3.5 bathrooms are available in the holiday home.
Mayors Manor, Zen Garden Oasis, Hot Tub & Sauna in Central Chicago, 8-12 guests
Chicago IL
During your stay at this holiday home, you'll be within walking distance of State Street. Enjoy features like 1 hot tub and laundry facilities. Free WiFi and a kitchen are available in the holiday home.
Newly Revamped Home - For privacy lovers
Chicago IL
During your stay at this holiday home, you'll be close to Harborside International Golf Center. The holiday home includes amenities such as free WiFi and a kitchen.
Lakefront property , minutes from McCormick Place and Downtown Chicago.
Chicago IL
During your stay at this holiday home, you'll be within walking distance of Lake Michigan. You'll find features such as laundry facilities. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.
“The Marlowe” A Couples Getaway
Chicago IL
During your stay at this holiday home, you'll be close to Abbott Park. Enjoy features like laundry facilities. The holiday home offers a kitchen and a fireplace.
Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago
Chicago IL
During your stay at this holiday home, you're just a quick walk from State Street. Enjoy features like laundry facilities. The holiday home offers free WiFi and in-room jetted baths.
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.
South Side Holiday Homes essential information
Accommodation | 91 Holiday Homes |
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Highest Price | |
Popular accommodation | LakeHouse, Lux Home in Chicago 7mins Downtown, Stay, Relax & Explore Chicago, Bronzeville Jazz Room. Beautiful, cozy, centered, relaxing, rustic., Charming house in amazing Chicago with WiFi and AC. Close to many restaurants., 1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown, A Home Away From Home!, Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!, Cheerful 4 bedroom smart home w/ indoor fireplace, Mayors Manor, Zen Garden Oasis, Hot Tub & Sauna in Central Chicago, 8-12 guests, Newly Revamped Home - For privacy lovers, Lakefront property , minutes from McCormick Place and Downtown Chicago. , “The Marlowe” A Couples Getaway, Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago, Relaxing hot and beautiful 4 bed, 2 baths in peaceful area |