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Vacation Rentals in Chicago

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New Listing! Unique 1BR Chicago Apartment w/Vintage Features - Walking Distance to Wrigley Field! – Property 3707920

  • Chicago rental - apartment, 1 bedroom, sleeps 4, 1 bathroom, Air Conditioning, Internet
  • $900/week
  • Calendar Last Updated On: Apr 18, 2014
Even the locals are surprised by the sheer amount of things to do in Chicago! From endless shopping, renowned museums, vibrant nightlife, and stunning...

Magnificent Mile luxury High Rise on 46th floor with great views – Property 3645756

  • Chicago rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, Hot Tub, Beach
  • $1,675 - $3,358/week
  • Calendar Last Updated On: Apr 18, 2014
Enjoy stunning city views looking east and south. This 46th floor condo is located in the heart of the River North neighborhood in one of Chicago’s premier high rise...

48th Floor high rise 2 bed / 2 bath with great views in the Magnificent Mile – Property 358020

  • Chicago rental - apartment, 2 bedrooms, sleeps 6, 2 bathrooms, Hot Tub, Downtown, Lake
  • $1,675 - $3,358/week
  • Calendar Last Updated On: Apr 18, 2014
Enjoy stunning panoramic city views looking northeast to southwest. This 48th floor unit is located in the heart of the River North neighborhood at one of Chicago’s...

Magnificent Mile luxury High Rise on 17th floor with great views – Property 3645758

  • Chicago rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, Beach, Communal Pool
  • $1,675 - $3,358/week
  • Calendar Last Updated On: Apr 18, 2014
Enjoy breathtaking city views looking west and south. This 17th floor condo is located in the heart of the River North neighborhood in one of Chicago’s premier high...

Magnificent Mile luxury High Rise on 24th floor with great views – Property 3645759

  • Chicago rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, Hot Tub, Beach
  • $1,675 - $3,358/week
  • Calendar Last Updated On: Apr 18, 2014
Enjoy stunning city views looking south and west. This 24th floor condo is located in the heart of the River North neighborhood in one of Chicago’s premier high rise...

Luxury 2 bedroom on 47th Floor with great views in Magnificent Mile – Property 379083

  • Chicago rental - apartment, 2 bedrooms, sleeps 6, 2 bathrooms, Downtown, Lake, Communal Pool
  • $1,675 - $3,358/week
  • Calendar Last Updated On: Apr 18, 2014
Enjoy stunning panoramic city views looking northeast to southwest. This 47th floor unit is located in the heart of the River North neighborhood at one of Chicago’s...

Magnificent Mile luxury High Rise on 28th floor with great views – Property 908613

  • Chicago rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, Hot Tub, Beach, Downtown, Lake
  • $1,675 - $3,358/week
  • Calendar Last Updated On: Apr 18, 2014
Enjoy stunning city views looking west and south. This 28th floor condo is located in the heart of the River North neighborhood in one of Chicago’s premier high rise...

Condo in Hot Bucktown / Wicker Park Neighborhood – Property 374687

  • Chicago rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, pets considered, Downtown
  • $1,325 - $2,422/week
  • Calendar Last Updated On: Apr 18, 2014
Chicago Premier Suites brings its impeccable service and luxurious amenities to this condo suite located in the heart of the urban hotspot Bucktown/Wicker Park...

New Luxury High Rise on 44th floor with 2 bed/2 bath and great views – Property 3645755

  • Chicago rental - apartment, 2 bedrooms, sleeps 6, 2 bathrooms, Hot Tub, Downtown
  • $1,675 - $3,358/week
  • Calendar Last Updated On: Apr 18, 2014
Stay in this 44th floor brand new luxury high rise building completed in 2013. Experience breathtaking city views in this Amli River North building located on the...

Magnificent Mile Luxury Corner Unit on 45th Floor with great views – Property 358005

  • Chicago rental - apartment, 2 bedrooms, sleeps 6, 2 bathrooms, Hot Tub, Downtown, Lake
  • $1,675 - $3,358/week
  • Calendar Last Updated On: Apr 18, 2014
Enjoy stunning panoramic city views looking northeast to southwest. This 45th floor unit is located in the heart of the River North neighborhood in one of Chicago’s...

Modern 2BD 1Bth Brick-Style Ranch! – Property 3733046

  • Chicago rental - house, 2 bedrooms, sleeps 5, 1 bathroom, pets considered, Village
  • Calendar Last Updated On: Apr 18, 2014
Very affordable home in west suburb that offers easy access to the city. Sleeps up to 5 people. -2 Bedrooms -1 Bathroom -Hardwood Floors -Tiled Bathroom...
SPECIAL OFFER! $99/night Apr Last Minute April 12 - May 15

$129/night in August. Downtown DISCOUNTED RATES!!!!! – Property 391029

  • Chicago rental - apartment, 1 bedroom, sleeps 2, 1 bathroom, accept credit card, Fitness Room / Equipment
  • $945/week
  • Calendar Last Updated On: Apr 17, 2014
Ammenities Include: *Gym * Cable TV & High Speed Internet Included Community Features Include: * Smoke-free residences * 24-hour door attendant * Emergency...

Teri's Chicago Guest House * Wrigley Suite * Wrigleyville – Property 319203

  • Chicago rental - apartment, 4 bedrooms, sleeps 8, 2 bathrooms, accept credit card, Downtown, Lake
  • $2,795/week
  • Calendar Last Updated On: Apr 17, 2014
Beautiful & Spacious! 1st Floor of the Three-Flat Walk in to the home and the first thing you notice is nothing has been taken for granted.

Your Sweet Chicago Home – Property 3471324

  • Chicago rental - apartment, 6 bedrooms, sleeps 14, 3 bathrooms, pets considered, Hot Tub
  • Calendar Last Updated On: Apr 17, 2014
With its large dining room table and brand new kitchen, this 5 bedroom Lincoln Park duplex is perfect for your group's get together. One block from Halsted St.

Millennium Park 2bd/2ba, WALK EVERYWHERE!!! – Property 391030

  • Chicago rental - apartment, 2 bedrooms, sleeps 4, 2 bathrooms, accept credit card, Fitness Room / Equipment
  • $1,400/week
  • Calendar Last Updated On: Apr 17, 2014
Posh and luxurious interiors, contemporary elegance, and a desirable location highlight , Chicago’s newest neighborhood, a prime area of downtown Chicago.

Wicker Park Russian Bathhouse 2bd LOFT – Property 391031

  • Chicago rental - apartment, 1 bedroom, sleeps 4, 1 bathroom, accept credit card, Hot Tub
  • $1,113/week
  • Calendar Last Updated On: Apr 17, 2014
The Chicago Bathhouse Corporate Residences are located on the 2nd floor of a 2 story building in Wicker Park Chicago. This vacation rentals are 2 bedrooms, 1...

3bds unit close to GRANT PARK – Property 391036

  • Chicago rental - apartment, 3 bedrooms, sleeps 6, 2 bathrooms, accept credit card, wheelchair accessible
  • $2,000/week
  • Calendar Last Updated On: Apr 17, 2014
We are offering a 2bd. unit on Michigan ave. Please inquire for more detailes.

Walk to everywhere! Millennium Park location – Property 391037

  • Chicago rental - apartment, 1 bedroom, sleeps 2, 1 bathroom, accept credit card, wheelchair accessible
  • $903/week
  • Calendar Last Updated On: Apr 17, 2014
Cheap small studio across the street from the Millennium Park , easy access to public transportation, walking distance from most downtown attractions.

Luxury and Value Close to Everything and McCormick Place Skyline View, Hot Tub – Property 271945

  • Chicago rental - apartment, 2 bedrooms, sleeps 6, 1 bathroom, 1 half bath, accept credit card, Hot Tub
  • $875 - $1,650/week
  • Calendar Last Updated On: Apr 17, 2014
We have a deck with an incredible skyline view of Chicago. That is the second picture below. The first picture is is our huge living/entertainment room.

Large Single Family Home in Chicago-walk to everything! Sleeps 9. – Property 389052

  • Chicago rental - house, 4 bedrooms, sleeps 9, 2 bathrooms, 1 half bath, accept credit card, Downtown
  • $7,500/week
  • Calendar Last Updated On: Apr 17, 2014
Wonderful Victorian three flat that was converted to a single family home. 4 levels of living space. Large back yard with deck.
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