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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.

Private room in Chicago
Cozy Chicago bedroom unit # 2 room # 3
A place you can come to and make memories. Hop on the CTA for a quick ride downtown, 20 minutes, to enjoy shopping and family friendly activities. You can also stay in to relax and enjoy coffee, tea, or hot chocolate at the self serve coffee bar. For a little more in house excitement, hang out in the photo / game room and have fun playing 2,000+ arcade games. You can also enjoy the Smart Tv to binge-watch all your favorite shows on Netflix. The perfect Airbnb for your next Chicago getaway.
$29 per night
SUPERHOST
Private room in Chicago
McCormick221, Chinatown, SOX, GrantPark
Feel free to check us other listings: https://www.airbnb.com/h/zengarden001 https://www.airbnb.com/h/zengarden331 https://www.airbnb.com/h/zengarden332 https://www.airbnb.com/h/zengarden333 A new renovated luxury zen garden step to Chicago loop, McCormick Place, Millennium Park, Navy Pier, SOX, Art Institute, UIC, IIT, UCHICAGO, Chinatown(hundreds of delicious food), Midway Airport. Perfect place for everyone in Chicago! Super easy free street parking!
$90 per night
SUPERHOST
Private room in Chicago
Luxury Stay near Downtown Chicago New Queen Bed
This stylish place to stay is perfect for guests looking to have a great airbnb experience. Enjoy the comfort of staying on home with brand new mattress, comforters, sheets, towels and everything else! Each room is equipped with Smart TV with Netflix, Amazon Videos and 300+ TV channels included, expensive luxury mattresses with 4 layers sheets & comforters bed setup, air conditioning with air humidifier, high speed internet and so much more!
$39 per night

Other great vacation rentals in South Side

Rental unit in Chicago
UChicago, Sci Museum | Lake View + Gym | Zencity
$99 per night
Rental unit in Chicago
Best Location in Hyde Park apartment
$78 per night
SUPERHOST
Private room in Chicago
Full Kitchen + All Essential Amenities
$39 per night
Private room in Chicago
Hyde Park/UC Newly Renovated Private Room #2
$59 per night
SUPERHOST
Private room in Chicago
Private room, Near IIT, DT, subway , free parking
$40 per night
Private room in Chicago
The Master Bedroom in Bridgeport Chicago
$50 per night
Private room in Chicago
25% off - Long Term Reservations
$36 per night
Private room in Chicago
Hyde Park/UC Modern Private Room 3
$58 per night
SUPERHOST
Private room in Chicago
Fully Remodeled Apartment & Spacious Queen Bed
$40 per night
Private room in Chicago
Living in a dream (unit 2 room #5)
$30 per night
SUPERHOST
Private room in Chicago
HydePark003, UC, NavyPier, Chinatown, freeparking
$78 per night
SUPERHOST
Private room in Chicago
Elegant Bedroom Near UChicago
$85 per night
SUPERHOST
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