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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 16, 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.

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...

Downtown Urban Oasis! Near Transit, Sites, Nightlife -- Huge Deck + Parking! – Property 3685036

  • Chicago rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, Hot Tub, Downtown
  • Calendar Last Updated On: Apr 16, 2014
Enjoy a stay at a world travelers' Windy City home! We'd love to welcome you into our newly renovated, upscale Chicago condo for short or long term stays.

Magnificent Mile, Gold Coast Luxury Brownstone Downtown Chicago Vacation Rental – Property 188897

  • Chicago rental - apartment, 2 bedrooms, sleeps 8, 2 bathrooms, accept credit card, Downtown, Lake
  • Calendar Last Updated On: Apr 16, 2014
Another First Class Chicago property! City of Chicago Vacation Rental License #2125365. Rent Legally! You've found it! Location, Location, Location!

Amazing Views of the Chicago Skyline from this Luxury Condo – Property 222038

  • Chicago rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, accept credit card, wheelchair accessible
  • $860 - $900/week
  • Calendar Last Updated On: Apr 16, 2014
See the amazing views of the entire Chicago Skyline from the top floor of this luxury executive condo located in the West Loop of Chicago.

Urban Luxury Home In Downtown Chicago! – Property 3656716

  • Chicago rental - house, 3 bedrooms, sleeps 11, 3 bathrooms, Hot Tub, Downtown
  • Calendar Last Updated On: Apr 16, 2014
Enjoy a stay at a world travelers' Windy City home! Modern, renovated, luxury Chicago condo is available for short or long term stays.

Heart Of Chicago-the Loop- For A Fraction Of The Price With Lots Of Amenities – Property 3603041

  • Chicago rental - condo, 1 bedroom, sleeps 3, 1 bathroom, wheelchair accessible, Downtown
  • $800 - $1,300/week
  • Calendar Last Updated On: Apr 15, 2014
Great one-bedroom unit in the Loop overlooking State Street on a quiet floor. Fully furnished with lots of natural light. High-ceilings, natural colored wood...

Featured On Travel Chanel With Views Of Wrigley Field, Beautiful New 4 Bedroom – Property 3646083

  • Chicago rental - condo, 4 bedrooms, sleeps 9, 2 bathrooms, Village, Air Conditioning
  • Calendar Last Updated On: Apr 16, 2014
The Inn at Wrigley Field understands that vacation rental fraud is pervasive. NEVER SEND MONEY TRANSFERS OR BANK WIRES TO MAKE YOUR RESERVATION.

Stop Searching! Chicago's Most Exclusive & Luxurious Residence – Property 923710

  • Chicago rental - apartment, 2 bedrooms, sleeps 6, 2 bathrooms, Hot Tub, wheelchair accessible
  • Calendar Last Updated On: Apr 16, 2014
You just found the perfect escape...Chicago's newest and most exclusive, luxurious residence will make your accommodations the memory of a lifetime. Offering an...
SPECIAL OFFER! Save 15% in April April 5 - April 30

Beautiful and Luxurious 3 Bedroom / 2 Bathroom Chicago Vacation Rental – Property 247326

  • Chicago rental - condo, 3 bedrooms, sleeps 8, 2 bathrooms, wheelchair accessible, Downtown, Lake
  • $1,830 - $2,340/week
  • Calendar Last Updated On: Apr 16, 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...

Spacious 2 bed, 2 bath luxury apartment close to Mag Mile. – Property 950736

  • Chicago rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, accept credit card, pets considered
  • $1,400/week
  • Calendar Last Updated On: Apr 14, 2014
Beautifully done high-end furnished 2BR, 2BA in Old Town w/12ft ceilings, hardwood flrs, chef's kitchen w/brkfst bar, in unit washer/dryer, Wood burning gas...

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 14, 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.

Beautiful 2 Bedroom, 2 Bath Chicago Vacation Rental Condo – Property 990184

  • Chicago rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, accept credit card, wheelchair accessible
  • $1,340 - $1,840/week
  • Calendar Last Updated On: Apr 14, 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...

Spacious&Charming in Wonderful Lincoln Square! Sleeps Up to 4! – Property 944458

  • Chicago rental - apartment, 2 bedrooms, sleeps 4, 1 bathroom, accept credit card, Downtown
  • Calendar Last Updated On: Apr 14, 2014
This apartment features a Queen Bed, Full Bed and a Roll Out Bed, Single Size is available for an additional fee. Conveniently located to all of Chicago's...

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 14, 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.

Beautifully Remodeled Corporate Apartment – Property 293044

  • Chicago rental - condo, 1 bedroom, sleeps 4, 1 bathroom, accept credit card, pets considered
  • Calendar Last Updated On: Apr 14, 2014
This architectural gem, located in the historical Printers Row area in the South Loop, is perfect for taking in all of Chicago's culture and beauty.

Magnificent Mile 2 Bedroom / 2 Bathroom Suite With Great City Views – Property 3727876

  • Chicago rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, pets considered, Hot Tub
  • $1,750 - $2,275/week
  • Calendar Last Updated On: Apr 13, 2014
Picture the things you love most about the city — the pace, the style, the impression that life is happening all around you. This 2 bedroom | 2 bath | 1320 square...

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 15, 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...

Enjoy 'Little Europe', Music, Microbrewery, and Much More! – Property 3751630

  • Chicago rental - apartment, 1 bedroom, sleeps 4, 1 bathroom, pets considered, Lawn / Garden
  • $470 - $660/week
  • Calendar Last Updated On: Apr 16, 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 16, 2014
***Stop Looking*** You've found your property*** ***Walk to Everything*** ***Enjoy Spacious Unit, Clean, New and Modern*** ***Enjoy Breathtaking Views of the...
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