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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...
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.

Great views-Luxury 2 bedroom on 32nd Floor Magnificent Mile – Property 358006

  • Chicago rental - apartment, 2 bedrooms, sleeps 6, 2 bathrooms, Hot Tub, Beach, Downtown
  • $1,675 - $3,358/week
  • Calendar Last Updated On: Apr 17, 2014
Enjoy stunning city views looking east and north. This 32nd floor apartment is located in the heart of the River North neighborhood next to the Gold Coast in one of...

Magnificent Mile luxury High Rise on 43rd floor with great views – Property 358013

  • Chicago rental - apartment, 2 bedrooms, sleeps 6, 2 bathrooms, pets considered, Hot Tub
  • $1,675 - $3,358/week
  • Calendar Last Updated On: Apr 17, 2014
Enjoy stunning panoramic city views looking northeast to southwest. This 43rd floor unit is located in the heart of the River North neighborhood in one of Chicago’s...

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.

Gorgeous 1 Bedroom Unit In Chicago – Property 3672022

  • Chicago rental - condo, 1 bedroom, sleeps 4, 1 bathroom, Fitness Room / Equipment, Internet
  • Calendar Last Updated On: Apr 17, 2014
Experience the vibrancy of down town Chicago and delight in the modern, sleek comfort of wyndham grand Chicago river front — an intimate haven on the magnificent...

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.

Value and Luxury. Close to City and McCormick Place. Skyline View and Hot Tub – Property 225815

  • Chicago rental - apartment, 3 bedrooms, sleeps 6, 1 bathroom, 1 half bath, accept credit card, Hot Tub
  • $875 - $1,650/week
  • Calendar Last Updated On: Apr 18, 2014
The view in our first picture is is the Chicago City Skyline view from our deck (closed in winter when there is snow and ice).

Lake Front Mansion Perfect For Your Family Reunion Or Corporate Retreat – Property 3628788

  • Chicago rental - house, 7 bedrooms, sleeps 24, 6 bathrooms, 1 half bath, Lawn / Garden, Air Conditioning
  • $7,500/week
  • Calendar Last Updated On: Apr 17, 2014
Start each day with a stunning sunrise over the lake! Lake Park Mansion is an exclusive Chicago vacation rental property conveniently located just 10 minutes from...

Chicago Loop Business District. Close to Sears Tower and Public Transportation – Property 391034

  • Chicago rental - apartment, 1 bedroom, sleeps 3, 1 bathroom, accept credit card, Beach, Downtown
  • $900/week
  • Calendar Last Updated On: Apr 17, 2014
The first new residential development built in the Chicago Central Business District since 1993, this location combines luxury and an ecologically conscious...

Perfect Chicago Location for Cubs Games & Lake Michigan Fun. – Property 3165875

  • Chicago rental - condo, 2 bedrooms, sleeps 5, 2 bathrooms, accept credit card, Lake
  • $1,320/week
  • Calendar Last Updated On: Apr 17, 2014
Spacious two bedroom/two bath condo is walking distance from beautiful Lake Michigan and Wrigley Field (.8 mi. away--10 minute walk), home of the Chicago Cubs.

Licensed VR 1bd sleep 4 in Logan Square, Historic Apartment in Historic Neighborhood !!! – Property 391038

  • Chicago rental - apartment, 1 bedroom, sleeps 4, 1 bathroom, Air Conditioning, Internet
  • $699/week
  • Calendar Last Updated On: Apr 17, 2014
UNIT AMENITIES • 1 flat screen TV, cable and HBO • Free Internet access • Fully furnished: dishware, pots and pans, coffeemaker (and coffee) • Sleeps 4 (queen bed,...

Great Location for Exploring Chicago on Foot. – Property 980980

  • Chicago rental - apartment, 1 bedroom, sleeps 3, 1 bathroom, accept credit card, Balcony
  • Calendar Last Updated On: Apr 17, 2014
1 Bedroom charming apartment available for rent in Old Town. The best thing about this place is the location, you can walk or take the EL (elevated train) everywhere...

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 16, 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...
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