Apartment vacation rentals in South Side
Find and book unique apartments on Airbnb
Top-rated apartment rentals in South Side
Guests agree: these apartments are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for South Side apartment rentals
Weekly apartment rentals
Rental unit in Berwyn
The Green Bungalow: Charming 1-BR apt. with patio
Rental unit in Chicago
Chicago Airbnb Newly Remodeled 2-Unit Apartment!
Rental unit in Chicago
2bdr apartment +free parking near train in Chicago
Rental unit in Chicago
*Entire City Apartment 1 block to Train Park Free
Rental unit in Chicago
Roomy Getaway in Vibrant Center of Lincoln Park
Rental unit in Chicago
Spacious 2BR on Quiet St - Free Park/Late Checkout
Rental unit in Chicago
A Vintage Pink House in the Heart of Chicago
Rental unit in Chicago
Free Parking & King Bed in Desirable Norwood Park!
Private apartment rentals
Rental unit in Chicago
Your Perfect Spot :)-With Memory Foam Mattress!
Rental unit in Chicago
Lovely 1-BR Apt with full kitchen & living room
Rental unit in Chicago
Stunning Basement Apartment w/free street parking!
Rental unit in Chicago
Beverly Cottage Loft
Rental unit in Chicago
Urban Cottage
Rental unit in Chicago
Flor de Luna ~ Little Village Chicago Retreat
Rental unit in Chicago
Location! Location! Location!
Rental unit in Chicago
Comfortable and Cozy Apartment
Apartment rentals with a hot tub
Rental unit in Chicago
Skyline Serenity: Sauna, Hot Tub, Peloton, Views
Rental unit in Chicago
Checkerboard Studio with Private Outdoor Hot Tub and Yard
Rental unit in Berwyn
“Dream slice of urban homesteading.”
Rental unit in Chicago
Cloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Rental unit in Chicago
Luxe Suite + Spa House Retreat! Pets Welcome
Rental unit in Chicago
The Areal Oasis
Rental unit in Chicago
Lake, City, & River View Condo
Rental unit in Chicago
Spectacular Rooftop Getaway in Heart of City
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