Vacation rentals in South Side

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Top-rated vacation rentals in South Side

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

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SUPERHOST
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.
$25 per night
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Private room · Chicago
Spectacular Downtown High Rise Extraordinary view
This newly renovated apartment building offers you everything you could dream of including an amazing view of the Iconic Chicago skyline through the it’s floor to ceiling windows. This unit specifically has a clean modern loft aesthetic.
$45 per night
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SUPERHOST
Entire condo · Chicago
Gorgeous 1 Bedroom Condo In Chicago
Newly renovated and furnished condominium unit welcomes you, with a full kitchen to fulfill any and all of your cooking needs. As well as one bedroom with a queen size bed capable of sleeping 2, and a fully furnished living room with a sofa bed capable of sleeping 2. The Metra thats only one block away can take you to the heart of downtown Chicago in 15 minutes. If you have a vehicle the condominium is only 6 blocks from Lake Shore Drive that can be taken to any major expressway in Chicago.
$91 per night

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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 vacation rentals in South Side

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Private room · Chicago
Perfect Oasis 4mins walk to University & hospital
$52 per night
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Private room · Chicago
Full bed w/Netflix near , UofChicago, and train
$46 per night
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Private room · Chicago
320 Peaceful Private RM in A Happy House W/Laundry
$36 per night
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Private room · Chicago
Room H6
$25 per night
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Entire rental unit · Chicago
Lovely 1 bedroom Condo in Hyde Park
$81 per night
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Private room · Chicago
Luxury Stay near Downtown Chicago New Queen bed
$42 per night
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SUPERHOST
Entire rental unit · Chicago
Lovely Entire 1 Bedroom Condo In Hyde Park
$129 per night
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SUPERHOST
Private room · Chicago
Cozy Chicago bedroom unit # 2 room # 3
$47 per night
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SUPERHOST
Private room · Chicago
HydePark001, UC, Chinatown,NavyPier, freeparking
$89 per night
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Private room · Chicago
Room H5
$24 per night
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SUPERHOST
Entire rental unit · Chicago
Royal Coach House Cottage
$108 per night
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SUPERHOST
Private room · Chicago
Hyde Park/UC Newly Renovated Private Room #3
$45 per night
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