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Holiday rentals in South Side

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in South Side

Guests agree: these stays are highly rated for location, cleanliness, and more.

Superhost
Guest house in Bridgeport
Private Studio in Bridgeport, Chicago
A bright studio guesthouse, perfect for business travelers, a couple’s getaway, personal retreat, or a solo adventurer. Has a kitchen sink, cabinet space for your non-perishable items, a microwave, mini-fridge, and Keurig. We provide plates, flatware, mugs, and glasses. The studio offers the privacy of your own bathroom and shower facilities. You'll rest well in a full-size Murphy bed, with sufficient storage for all your travel items. A couch is available for a third guest if needed.
$78 SGD per night
Superhost
Home in Wicker Park
Division St Designer Home In Heart of Wicker Park
Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).
$133 SGD per night
Superhost
Apartment in Lake View
Urban Comfort in the Heart of Chicago
Proud to be amongst the highest rated listings in the city. This is the PRIVATE first floor of our duplex condo, with your own entrance/exit, 75" flatscreen TV, central heat/air, and an en-suite bathroom. We are in the middle of Chicago's vibrant Northside while still having the benefit of coming home to a tree lined one lane residential street. Please contact us with any questions at all before you book your stay.
$154 SGD per night

Other great holiday rentals in South Side

Superhost
Flat in Chicago
La Cottage
$98 SGD per night
Superhost
Flat in Wicker Park
Newly remodeled 1BR! Only 5 MIN walk to BLUE LINE!
$144 SGD per night
Superhost
Flat in Wicker Park
Private Studio Apt in the Heart of Wicker Park!
$125 SGD per night
Superhost
Guest suite in Bridgeport
Clean, Cozy, Comfortable Studio Near Downtown
$92 SGD per night
Superhost
Flat in Pilsen Historic District
Spectacular Pilsen Studio for 2!
$70 SGD per night
Superhost
Flat in Pilsen Historic District
Modern
$108 SGD per night
Superhost
Loft in Lake View
Lakeview Loft-Vintage Chicago, Modern Amenities
$177 SGD per night
Superhost
Guest suite in Chicago
Comfy/Private Entry & Bath/Free Parking - Win Win!
$94 SGD per night
Superhost
Guest suite in Andersonville
Gorgeous, cozy 1-bedroom Suite in Andersonville
$117 SGD per night
Superhost
Flat in Irving Park
Explore Chicago from an Urban Sanctuary with Free Parking
$50 SGD per night
Superhost
Loft in Brighton Park
Entire place with free parking.
$84 SGD per night
Superhost
Guest suite in Hyde Park
Convenient Hyde Park 2 Bedroom Apartment
$134 SGD per night

Destinations to explore

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