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Vacation rentals in South Side

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in South Side

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

Superhost
Apartment in Wicker Park
Newly remodeled 1BR! Only 5 MIN walk to BLUE LINE!
Located in the heart of Wicker Park, just a 5 min walk to the Damen blue line stop. This phenomenal location allows you to access EVERYTHING Chicago has to offer without having to rent a car. Experience the best of Chicago, all within a short walk from your stay. World class bars, restaurants, and shopping all within walking distance. Want to explore downtown or catch a Cubs game at Wrigley? Hop on the "L" train and use the CTA to go anywhere in the city. This cozy garden apartment has it all.
$110 per night
Superhost
Guesthouse 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.
$63 per night
Superhost
Condo 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.
$101 per night

Other great vacation rentals in South Side

Superhost
Apartment in Chicago
La Cottage
$71 per night
Superhost
Apartment in Pilsen Historic District
Spectacular Pilsen Studio for 2!
$52 per night
Superhost
Apartment in Wicker Park
Private Studio Apt in the Heart of Wicker Park!
$99 per night
Superhost
Guest suite in Bridgeport
Clean, Cozy, Comfortable Studio Near Downtown
$69 per night
Superhost
Home in Wicker Park
Division St Designer Home In Heart of Wicker Park
$99 per night
Superhost
Apartment in Pilsen Historic District
Modern
$82 per night
Superhost
Loft in Lake View
Lakeview Loft-Vintage Chicago, Modern Amenities
$117 per night
Superhost
Guest suite in McKinley Park
Vintage Suite Home Chicago by Sox/Park/Transit
$70 per night
Superhost
Guest suite in Andersonville
Gorgeous, cozy 1-bedroom Suite in Andersonville
$87 per night
Superhost
Guest suite in Chicago
Comfy/Private Entry & Bath/Free Parking - Win Win!
$71 per night
Superhost
Apartment in Irving Park
Explore Chicago from an Urban Sanctuary with Free Parking
$38 per night
Superhost
Loft in Brighton Park
Entire place with free parking.
$63 per night

Destinations to explore

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  6. South Side