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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.

Private Studio in Bridgeport, Chicago
SUPERHOST
Entire guesthouse · 3 guests · 1 bed · 1 bath
Private Studio in Bridgeport, ChicagoA 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.
Polk Street Coach House Apartment, Little Italy/Medical Dist
PLUS
Entire guesthouse · 6 guests · 2 beds · 1 bath
Polk Street Coach House Apartment, Little Italy/Medical DistCook in a kitchen with everything from a KitchenAir convection range and Kitchen Aid food processor to Calphalon pots and pans. The mid-century look includes a comfy American Leather sofa, Gansgo Mobler dining table, and Frem Rolje teak chairs.
Perfect Private Getaway in Perfect Pilsen
SUPERHOST
Entire guest suite · 2 guests · 1 bed · 1 bath
Perfect Private Getaway in Perfect PilsenThis quiet and cozy studio in Pilsen is the perfect place to rest your head after a long day of exploring the Windy City. With so much to do in the area and easy access to public transit, you won't run out of ways to spend your time! Close to Chinatown, the United Center, and the Medical District, and downtown is a quick train ride away on the Pink Line. Relax in this thoughtfully designed space, perfect for couples or business travelers. Book today! Please note: ceiling height is about 6'3"

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Other great vacation rentals in South Side

PLUS
  1. Entire residential home
  2. Chicago
Get Cozy at a Powder-Blue Residence in the Heart of Pilsen
$94 per night
SUPERHOST
  1. Private room
  2. Chicago
Restoring Chicago speakeasy of the 1920s. Room 4A
$90 per night
  1. Entire condominium (condo)
  2. Chicago
Lovely 1-bedroom condo in Hyde park by lake
$83 per night
  1. Entire rental unit
  2. Chicago
Cozy 2Bd Apartment in Pilsen
$70 per night
SUPERHOST
  1. Private room
  2. Chicago
🌟 Cozy Bedroom by Downtown & Train; Rooftop Deck!🌟
$41 per night
SUPERHOST
  1. Entire townhouse
  2. Chicago
CITY CONDO with GARAGE 7 min Walk to Train
$56 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Royal Coach House Cottage
$105 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Cabin #208 at 747 Lofts
$79 per night
PLUS
  1. Entire loft
  2. Chicago
Pilsen Modernist, Creative, Lightfilled Loft
$114 per night
SUPERHOST
  1. Private room
  2. Chicago
Private BR in Condo close to Chicago Dwtwn!
$77 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Grand Avenue APT 2/West Loop & newly renovated!
$146 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Lovely Entire 1 Bedroom Condo In Hyde Park
$68 per night