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Vacation rentals in Downtown Chicago

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Top-rated vacation rentals in Downtown Chicago

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

Lakeview Loft-Vintage Chicago, Modern Amenities
SUPERHOST
Entire loft · 4 guests · 2 beds · 1 bath

Lakeview Loft-Vintage Chicago, Modern AmenitiesThe Lakeview Loft is a freshly remodeled loft space with a vintage Chicago theme and modern amenities. Located in the Lakeview neighborhood, it is 1/2 mile to the Brown & Red Line el trains, less than a mile to Wrigley Field and 1.5 miles to the lakefront. The Lakeview Loft will provide guests a true Chicago experience while staying in a great Chicago neighborhood. We believe in giving back to our neighborhood as well so for each booking we donate $5 to a local children's charity.

Great location. Free parking.  One night available
SUPERHOST
Entire apartment · 2 guests · 1 bed · 1 bath

Great location. Free parking. One night availableGreat location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

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.

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Popular amenities for Downtown Chicago vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Downtown Chicago

SUPERHOST
  1. Entire condominium
  2. Chicago
Walkable Location/Fast Wifi/Near Parks & Dining
$121 per night
SUPERHOST
  1. Private room
  2. Chicago
Self check in near Downtown Chicago
$36 per night
SUPERHOST
  1. Private room
  2. Chicago
Quiet and safe neighborhood. Amazing Lincoln Park
$34 per night
SUPERHOST
  1. Entire guest suite
  2. Chicago
Clean, Cozy, Comfortable Studio Near Downtown
$67 per night
  1. Entire apartment
  2. Chicago
New Spot in West Town
$71 per night
  1. Entire apartment
  2. Chicago
Spacious 2 Bedroom in the heart of Lakeview!
$150 per night
SUPERHOST
  1. Private room
  2. Chicago
Restoring Chicago Speakeasy from 1920's Room 1A
$100 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Spacious corner 3BR w city view & optional parking
$223 per night
  1. Entire guest suite
  2. Chicago
Remodeled Suite in a prime West Town location!
$86 per night
SUPERHOST
  1. Private room
  2. Chicago
SHARED Artist Loft . Very Unique
$99 per night
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  1. Entire apartment
  2. Chicago
The Photographers' Place
$85 per night
SUPERHOST
  1. Entire condominium
  2. Chicago
Urban Comfort in the Heart of Chicago
$109 per night

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