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Vacation Rental Homes, Apartments & Condos for Rent in Chicago, Illinois

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Large Luxury Home near Downtown Chicago — Property 169076

  • House
  • 5 bedrooms, sleeps 15
  • 4 bathrooms, 1 half bath
  • downtown, river
  • accept credit card
Rates per property (USD)
$1,075/night
$5,500/week
$15,000/month

Magnificent Mile , Gold Coast Luxury Brownstone Downtown! — Property 188897

  • Apartment
  • 2 bedrooms, sleeps 6
  • 2 bathrooms
  • downtown, lake
  • accept credit card
Rates per property (USD)
$275 - $400/night

Modern 4 Level Home. Minutes from Downtown — Property 183649

  • House
  • 4 bedrooms, sleeps 10
  • 3 bathrooms, 1 half bath
  • downtown, lake
  • accept credit card
Rates per property (USD)
$350 - $495/night
$2,500 - $2,700/week
$8,000/month

Chicago Guest House-Nowhere Will You Feel More At Home! — Property 116901

  • House
  • 3 bedrooms, sleeps 6
  • 3 bathrooms
  • downtown, lake
  • accept credit card
Rates per property (USD)
$425/night

Luxury Condo with Stunning Chicago Skyline and River Views, Perfect Location — Property 184807

  • Condo
  • 2 bedrooms, sleeps 6
  • 2 bathrooms
  • downtown, river
  • accept credit card
Rates per property (USD)
$299/night
$1,895/week

Lincoln Park Oasis — Property 160572

  • Condo
  • 3 bedrooms, sleeps 9
  • 1 bathroom
  • downtown
  • accept credit card
Rates per property (USD)
$215/night

Chicago Guest House-Wrigley Suite 'Wrigleyville' — Property 319203

  • Apartment
  • 4 bedrooms, sleeps 8
  • 2 bathrooms
  • downtown, lake
  • accept credit card
Rates per property (USD)
$495/night

Chicago Guest House on Lakewood 'Wrigleyville' — Property 319468

  • Apartment
  • 3 bedrooms, sleeps 6
  • 2 bathrooms
  • downtown, lake
  • accept credit card
Rates per property (USD)
$380/night

Classic Victorian Greystone in Chicago's Wrigleyville! — Property 170782

  • Apartment
  • 3 bedrooms, sleeps 5
  • 1 bathroom
  • downtown, lake
  • accept credit card
Rates per property (USD)
$1,820/week

Discontinued — Property 89344

  • 1 bedroom, sleeps 1
  • 1 bathroom
Rates per property (USD)
$1,000 - $10,000/night
$10,000/week

DISCOUNT Days 7/13-27!!! Goldcoast High-Rise 4-6 people — Property 168042

  • Condo
  • 2 bedrooms, sleeps 4
  • 1 bathroom
  • beach, downtown
  • accept credit card
Rates per property (USD)
$200 - $275/night
$1,400 - $1,750/week
$3,600/month

New Downtown Condo!! Award winning Location — Property 172675

  • Condo
  • 1 bedroom, sleeps 4
  • 1 bathroom
  • downtown, waterfront
  • accept credit card
Rates per property (USD)
$295/night
$1,995/week

Chicago Guest House -Clark Suite 'Wrigleyville' — Property 146193

  • Apartment
  • 3 bedrooms, sleeps 8
  • 2 bathrooms
  • downtown, lake
  • accept credit card
Rates per property (USD)
$450/night

Beautiful 3 Bedroom South Loop TH w/ yard, easy parking, cable and Internet — Property 169185

  • Townhome
  • 3 bedrooms, sleeps 8
  • 3 bathrooms
  • downtown, lake
  • air-conditioning
Rates per property (USD)
$2,000/week
$6,000/month

Chicago Guest House-Lakeview Suite 'Wrigleyville' — Property 153025

  • Condo
  • 3 bedrooms, sleeps 6
  • 2 bathrooms
  • downtown, lake
  • accept credit card
Rates per property (USD)
$380/night
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