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Vacation Rentals in Chicago

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Recently Renovated 2BR Condo in Old Town - Walk to Lake Michigan! – Property 3613575

  • Chicago rental - condo, 2 bedrooms, sleeps 5, 2 bathrooms, Balcony, Air Conditioning
  • $2,200/week
  • Calendar Last Updated On: Apr 22, 2014
Chicago, with its towering skyscrapers and sandy beaches, is one of the most visited cities in the Midwest, and it’s easy to see why.

Teri's Chicago Guest House * Shoreline Suite * Wrigleyville – Property 319468

  • Chicago rental - apartment, 3 bedrooms, sleeps 6, 2 bathrooms, accept credit card, Downtown, Lake
  • $2,179/week
  • Calendar Last Updated On: Apr 22, 2014
Walk in to the home and the first thing you notice is nothing has been taken for granted. You’ll be engulfed in warm inviting hues.

Lovely 2-flat in Lincoln Park, near downtown Chicago, museums, shopping, Lake MI – Property 919979

  • Chicago rental - apartment, 3 bedrooms, sleeps 6, 1 bathroom, accept credit card, Downtown, Lake
  • $1,500/week
  • Calendar Last Updated On: Apr 22, 2014
Our classic Chicago apartment is located in a traditional brick and stone 2 unit walk up. It has been lovingly restored and updated to provide both a sense of...

Magnificent Northside Brownstone Home – Property 211715

  • Chicago rental - house, 5 bedrooms, sleeps 13, 3 bathrooms, accept credit card, Air Conditioning
  • $3,333/week
  • Calendar Last Updated On: Apr 22, 2014
Enjoy this newly completed high-end renovation of a classic Brownstone home with 5 spacious bedrooms, 3 full baths, two full Living Rooms with full theater surround...

Cozy home away from home located 25 minutes from downtown Chicago – Property 247191

  • Chicago rental - house, 2 bedrooms, sleeps 6, 1 bathroom, accept credit card, Air Conditioning
  • $775/week
  • Calendar Last Updated On: Apr 22, 2014
This cozy home is located 25 minutes south of Chicago and is 1 mile from the expressway to the City. Great location for visiting family members.

Lakeshore, Millennium Park High Rise – Property 204526

  • Chicago rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, accept credit card, wheelchair accessible
  • Calendar Last Updated On: Apr 21, 2014
Chicago's most trusted Housing Provider! Spacious Chicago high rise with sun-kissed corner unit! Location, Location, Location: Ideally situated between Navy Pier...

Fabulous Lincoln Park Apartment near DePaul Univ; Only Owner Managed – Property 296798

  • Chicago rental - condo, 3 bedrooms, sleeps 8, 2 bathrooms, accept credit card, Downtown, Lake
  • $1,879 - $2,005/week
  • Calendar Last Updated On: Apr 21, 2014
This 1550 sq ft. beautiful unit is in the heart of Lincoln Park. Travel and live like a Chicago local in our home. The bathroom floors are heated for extra comfort.

Wonderful Lincoln Park/DePaul Apartment In A Great Location,Only Owner Managed – Property 939473

  • Chicago rental - condo, 3 bedrooms, sleeps 8, 2 bathrooms, accept credit card, Downtown
  • $1,844 - $2,040/week
  • Calendar Last Updated On: Apr 22, 2014
Victorian 1500 sq ft. beautiful unit is in the heart of Lincoln Park. Live like a Chicago local in our home. There is a TV in the first bathroom as well as in all...

Modern 2 BD condo with pkg beautifully furnished 20 min to downtown – Property 948576

  • Chicago rental - condo, 2 bedrooms, sleeps 5, 1 bathroom, Downtown, Lake, Jacuzzi
  • $700/week
  • Calendar Last Updated On: Apr 21, 2014
Modern 2 BD city apt. beautifully furnished, granite bath with Jacuzzi, fully equipped kitchen. Bright and sunny apt in 4 unit condo building.

Wake to Sunrise Over Lake Michigan! Spacious with Stunning Views! – Property 3671329

  • Chicago rental - condo, 1 bedroom, sleeps 4, 1 bathroom, wheelchair accessible, Communal Pool
  • $1,150 - $1,400/week
  • Calendar Last Updated On: Apr 22, 2014
Unit features: * pillow-top queen bed in bedroom * full size futon in LR for extra guests * WIFI, cable TV, and DVD * fully equipped kitchen with all cooking...

Luxury Highrise Suite with Panoramic Views of Chicago's Skyline – Property 378791

  • Chicago rental - condo, 1 bedroom, sleeps 2, 1 bathroom, accept credit card, pets considered
  • Calendar Last Updated On: Apr 21, 2014
Columbus Plaza is a sophisticated high rise located in Chicago's premium loop area near the Magnificent Mile and Millennium Park.
SPECIAL OFFER! Book Now and Save! April 5 - April 30

Beautiful and Luxurious Andersonville 2 BR /2 BA – Property 974965

  • Chicago rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, accept credit card, wheelchair accessible
  • $1,980/week
  • Calendar Last Updated On: Apr 20, 2014
Want to live like a local while staying in Chicago? Our Chicago vacation rental offers an affordable and comfortable place to lay your head during your visit to our...

Enjoy 'Little Europe', Park, Music, Other Great Venues at Low Introductory Rate! – Property 3751630

  • Chicago rental - apartment, 1 bedroom, sleeps 4, 1 bathroom, Lawn / Garden, Balcony
  • $470 - $660/week
  • Calendar Last Updated On: Apr 21, 2014
Comfy, quiet and discreet space for value seekers who want the full city experience in a cozy and convenient location. Ideal for a couple that wants to soak in...

3bd/2.5baX **Walk to Everything!** Breathtaking Views of the City and Lake*** – Property 267014

  • Chicago rental - condo, 3 bedrooms, sleeps 30, 2 bathrooms, 1 half bath, Downtown
  • Calendar Last Updated On: Apr 22, 2014
***Stop Looking*** You've found your property*** ***Walk to Everything*** ***Enjoy Spacious Unit, Clean, New and Modern*** ***Enjoy Breathtaking Views of the...

3bd/2.5baX ** Walk to Everything! *** Stunning Views of the Lake and City – Property 267015

  • Chicago rental - condo, 3 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, Lake, Town
  • Calendar Last Updated On: Apr 22, 2014
Spectacular Views. Come experience and enjoy Chicago. Visit museums, shops, restaurants, the Navy Pier, shows and more! *We thank you for your interest in our...

Charming&Spacious in Wonderful Lincoln Square! Sleeps Up to 4! – Property 3000573

  • Chicago rental - apartment, 1 bedroom, sleeps 4, 1 bathroom, accept credit card, Air Conditioning
  • Calendar Last Updated On: Apr 19, 2014
This apartment features a Queen Bed, Queen Sofa Bed and a Roll Out Bed, Single Size is available for an additional fee. Charming and Spacious 4 Room Vintage...

Luxury Studio, Steps To Everything – Property 3652455

  • Chicago rental - studio, 1 bedroom, sleeps 3, 1 bathroom, Hot Tub, wheelchair accessible
  • Calendar Last Updated On: Apr 20, 2014
I've lived here for five years and it keeps getting better and better. We're located in Streeterville (downtown Chicago). The building is just two blocks from Lake...

Modern Luxury In Wicker Park, 14 Day Minimum Stay – Property 3641657

  • Chicago rental - house, 3 bedrooms, sleeps 6, 5 bathrooms, pets considered, Balcony
  • Calendar Last Updated On: Apr 21, 2014
Architecturally significant single family home in chicago's best neighborhood, wicker park. This home has been featured in design magazines and is ideal for...

Beautiful Old Town Chicago Penthouse – Property 383734

  • Chicago rental - apartment, 3 bedrooms, sleeps 8, 2 bathrooms, Downtown, Air Conditioning
  • Calendar Last Updated On: Apr 22, 2014
This beautiful 2500 sq. ft penthouse in the heart of downtown Chicago is sponsored by TopstepTrader. 3 Bedroom, 2 Bathroom Condo The unit is next to 'Magnificent...

Luxury Resort in the Heart of Downtown Chicago – Property 242128

  • Chicago rental - apartment, 2 bedrooms, sleeps 6, 2 bathrooms, accept credit card, Hot Tub
  • Calendar Last Updated On: Apr 22, 2014
Brand new luxury 2 bedroom 2 bathroom corporate housing suite in a building resort unlike anything in Chicago!! The Resort is located in Chicago's high end...
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