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Vacation rentals in South Loop, Chicago

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Top-rated vacation rentals in South Loop, Chicago

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.
Restoring Chicago speakeasy of the 1920s room 3A
SUPERHOST
Private room · 2 guests · 1 bed · 1 private bath
Restoring Chicago speakeasy of the 1920s room 3AIf you are having trouble booking a night call me. Michael: 3124515213 My son Todd and I are currently restoring a gem from Chicago's history. we have made great progress in the last year and now our down to simple painting touch-ups Come be part of it. M&T
Get Cozy at a Powder-Blue Residence in the Heart of Pilsen
PLUS
Entire residential home · 4 guests · 2 beds · 1 bath
Get Cozy at a Powder-Blue Residence in the Heart of PilsenStep into the sleek, all-white tiled bathroom for an energising morning shower, then gather around the chunky kitchen table for a lazy breakfast. The soft, muted tones and warm hardwood floors at this urban sanctuary make for a chilled vibe.

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Other great vacation rentals in South Loop, Chicago

SUPERHOST
  1. Entire rental unit
  2. Chicago
Beautiful and spacious West Loop apartment.
$170 per night
  1. Entire rental unit
  2. Chicago
The Executive's Escape (2BR)
$225 per night
SUPERHOST
  1. Private room
  2. Chicago
SHARED Artist Loft . Very Unique
$90 per night
SUPERHOST
  1. Entire condominium (condo)
  2. Chicago
Magnificent corner apt w optional parking/sleeps 6
$139 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Corner heaven 2b/2b w optional parking/sleeps 6
$170 per night
SUPERHOST
  1. Entire condominium (condo)
  2. Chicago
Lovely 1BR Private Condo Steps From McCormick Pl!
$59 per night
SUPERHOST
  1. Entire guest suite
  2. Chicago
Comfortable & Cozy in Bridgeport
$66 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Teeny Tiny Bohemian Lodge - Clean & Affordable
$42 per night
  1. Entire condominium (condo)
  2. Chicago
Michigan Ave KING BEDS #5 | Grant Park 2bd/2ba
$102 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
1-Bedroom Close to Downtown/Chinatown/White Sox
$44 per night
  1. Entire loft
  2. Chicago
Downtown CROWN #5 2bd/2ba +GYM | Near Museums
$90 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Luxury Corner 2BR Penthouse in the Loop | Roof Deck
$189 per night