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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.

Private room · Chicago
Living in a dream (unit 2 room #5)
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.
$40 SGD per night
SUPERHOST
Private room · Chicago
HydePark002, UC, NavyPier, Chinatown, freeparking
Feel free to check us other listings: https://www.airbnb.com/h/hydepark001 https://www.airbnb.com/h/zengarden333 https://www.airbnb.com/h/zengarden332 https://www.airbnb.com/h/zengarden001 Hyde Park luxury private room with a keypad lock on each room door. Shared full bathroom only for 2 rooms. Step to UChicago, Chicago loop, McCormick, Chinatown(hundreds of delicious food). Perfect for everyone in Chicago! Free street parking.
$99 SGD per night
SUPERHOST
Private room · Chicago
Hyde Park/UC Newly Renovated Private Room #2
This bright private room is in a newly renovated townhome at Hyde Park, blocks away from University of Chicago medical center and its main campus. Free internet and free Parking on the street. Keypad on the room door is to double secure your privacy. Self check-in and check-out.
$96 SGD per night
SUPERHOST

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Stay near South Side's top sights

Photo of Museum of Science and Industry, Chicago
Museum of Science and Industry, Chicago191 locals recommend
Photo of McCormick Place
McCormick Place63 locals recommend
Photo of Frederick C. Robie House
Frederick C. Robie House32 locals recommend
Photo of South Shore Cultural Center
South Shore Cultural Center10 locals recommend
Photo of University of Chicago: Hyde Park
University of Chicago: Hyde Park5 locals recommend
Photo of McCormick Place
McCormick Place63 locals recommend

Other great holiday rentals in South Side

Private room · Chicago
Hyde Park/UC Newly Renovated Private Room #3
$64 SGD per night
SUPERHOST
Entire apartment · Chicago
Gorgeous 1 Bedroom Condo In Chicago
$126 SGD per night
SUPERHOST
Entire rental unit · Chicago
Royal Coach House Cottage
$155 SGD per night
SUPERHOST
Private room · Chicago
City View near Downtown Chicago Sox & Chinatown
$71 SGD per night
Entire rental unit · Chicago
Lovely 1 bedroom Condo in Hyde Park
$116 SGD per night
Hotel room · Chicago
♣️ HUGE 420 FRIENDLY MASTER 2 BEDROOM CONDO
$298 SGD per night
Private room · Chicago
Safe Haven - Feels like your own place
$44 SGD per night
Entire rental unit · Chicago
Your get-away to Canaryville in Chicago (unit 1R)
$121 SGD per night
SUPERHOST
Private room · Chicago
Full bed w/Netflix near , UofChicago, and train
$67 SGD per night
Entire rental unit · Chicago
BEST In Chicago. Entire condo w/FREE Gated parking
$143 SGD per night
SUPERHOST
Private room · Chicago
Cozy Chicago bedroom unit # 2 room # 3
$68 SGD per night
SUPERHOST
Private room · Chicago
HydePark007, Chinatown, UC, NavyPier, freeparking
$129 SGD per night
SUPERHOST
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