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Vacation Rentals in Chicago, Illinois(224)

USA >
CHICAGO
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Beach Rental
    2 Bedrooms,
  • 1 Bathroom
    • , Sleeps 5
  • Viewed

Beach Rental

2 Bedrooms,
  • 1 Bathroom
    • , Sleeps 5
    1. Illinois  >
    2. Chicago Cottage
    #317789vb

    3 br apartment, 2 bathrooms & half bathroom, unbelievable views from the terrace
      3 Bedrooms,
    • 2 Bathrooms, 
    • 1 Half Bath
      • , Sleeps 8
    • Viewed

    3 br apartment, 2 bathrooms & half bathroom, unbelievable views from the terrace

    3 Bedrooms,
  • 2 Bathrooms, 
  • 1 Half Bath
    • , Sleeps 8
    1. Illinois  >
    2. Chicago Apartment
    #83872

    Available Memorial Day Weekend-Amazing Skyline, Lake, River Views, Walk to All
      2 Bedrooms,
    • 2 Bathrooms
      • , Sleeps 6
    • Viewed

    Available Memorial Day Weekend-Amazing Skyline, Lake, River Views, Walk to All

    2 Bedrooms,
  • 2 Bathrooms
    • , Sleeps 6
    1. Illinois  >
    2. Chicago Apartment
    #408313vb


    Modern 2 BD condo with pkg beautifully furnished 20 min to downtown
      2 Bedrooms,
    • 1 Bathroom
      • , Sleeps 5
    • Viewed

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

    2 Bedrooms,
  • 1 Bathroom
    • , Sleeps 5
    1. Illinois  >
    2. Chicago Condo
    #948576

    C$113 - C$128
    per night (C$)
    3 night Minimum Stay
    Beautiful modern loft close to Chicago attractions and McCormick Place
      1 Bedrooms,
    • 1 Bathroom
      • , Sleeps 4
    • Viewed

    Beautiful modern loft close to Chicago attractions and McCormick Place

    1 Bedrooms,
  • 1 Bathroom
    • , Sleeps 4
    1. Illinois  >
    2. Chicago Condo
    #902863

    C$164 - C$185
    per night (C$)
    3 night Minimum Stay
    Beautiful Wicker Park 1 Bed
      1 Bedrooms, Sleeps 3
    • Viewed

    Beautiful Wicker Park 1 Bed

    1 Bedrooms, Sleeps 3
    1. Illinois  >
    2. Chicago Condo
    #299967vb

    C$128
    per night (C$)
    3 night Minimum Stay
    Enjoy Fab Lake and Skyline Views + Luxury Comfort at Prime Downtown Location!!
      2 Bedrooms,
    • 2 Bathrooms
      • , Sleeps 6
    • Viewed

    Enjoy Fab Lake and Skyline Views + Luxury Comfort at Prime Downtown Location!!

    2 Bedrooms,
  • 2 Bathrooms
    • , Sleeps 6
    1. Illinois  >
    2. Chicago Condo
    #177863

    C$308
    per night (C$)
    2 night Minimum Stay
    Penthouse Duplex #2
      3 Bedrooms,
    • 3 Bathrooms
      • , Sleeps 8
    • Viewed

    Penthouse Duplex #2

    3 Bedrooms,
  • 3 Bathrooms
    • , Sleeps 8
    1. Illinois  >
    2. Chicago Condo
    #109064vb

    C$616 - C$822
    per night (C$)
    3 - 4 night Minimum Stay
    Penthouse #5
      1 Bedrooms,
    • 1 Bathroom
      • , Sleeps 4
    • Viewed

    Penthouse #5

    1 Bedrooms,
  • 1 Bathroom
    • , Sleeps 4
    1. Illinois  >
    2. Chicago Condo
    #65673vb

    C$257 - C$308
    per night (C$)
    3 night Minimum Stay
    4br 3.5 Bath Townhouse Near Chinatown
      4 Bedrooms,
    • 3 Bathrooms, 
    • 1 Half Bath
      • , Sleeps 12
    • Viewed

    4br 3.5 Bath Townhouse Near Chinatown

    4 Bedrooms,
  • 3 Bathrooms, 
  • 1 Half Bath
    • , Sleeps 12
    1. Illinois  >
    2. Chicago Townhome
    #441679vb

    C$102 - C$132
    per night (C$)
    2 night Minimum Stay
    1 Bedroom - Magnificent Mile and Navy Pier
      1 Bedrooms,
    • 1 Bathroom
      • , Sleeps 4
    • Viewed

    1 Bedroom - Magnificent Mile and Navy Pier

    1 Bedrooms,
  • 1 Bathroom
    • , Sleeps 4
    1. Illinois  >
    2. Chicago Apartment
    #397011vb

    C$149 - C$167
    per night (C$)
    2 - 3 night Minimum Stay
    May Special from $135/nt -Top Location-Magnificent Mile & Navy Pier
      Studio,
    • 1 Bathroom
      • , Sleeps 4
    • Viewed

    May Special from $135/nt -Top Location-Magnificent Mile & Navy Pier

    Studio,
  • 1 Bathroom
    • , Sleeps 4
    1. Illinois  >
    2. Chicago Studio
    #929696

    C$157 - C$162
    per night (C$)
    2 - 3 night Minimum Stay
    Magnificent Mile luxury High Rise on 28th floor with great views
      2 Bedrooms,
    • 2 Bathrooms
      • , Sleeps 6
    • Viewed

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

    2 Bedrooms,
  • 2 Bathrooms
    • , Sleeps 6
    1. Illinois  >
    2. Chicago Condo
    #908613

    C$231 - C$477
    per night (C$)
    3 - 7 night Minimum Stay
    Wrigleyville/Southport Corridor Luxury Inn Walk to Wrigley Field/Cubs
      2 Bedrooms,
    • 1 Bathroom
      • , Sleeps 7
    • Viewed

    Wrigleyville/Southport Corridor Luxury Inn Walk to Wrigley Field/Cubs

    2 Bedrooms,
  • 1 Bathroom
    • , Sleeps 7
    1. Illinois  >
    2. Chicago Condo
    #203741

    Lincoln park New rehabbed and new furniture, awesome location, Depaul
      3 Bedrooms,
    • 1 Bathroom
      • , Sleeps 6
    • Viewed

    Lincoln park New rehabbed and new furniture, awesome location, Depaul

    3 Bedrooms,
  • 1 Bathroom
    • , Sleeps 6
    1. Illinois  >
    2. Chicago Apartment
    #3166511

    C$257
    per night (C$)
    2 night Minimum Stay
    Great Location, Modern, Lakeview, Roscoe Village,Close to Cubs
      2 Bedrooms, Sleeps 6
    • Viewed

    Great Location, Modern, Lakeview, Roscoe Village,Close to Cubs

    2 Bedrooms, Sleeps 6
    1. Illinois  >
    2. Chicago Apartment
    #179461vb

    Luxury Penthouse Lincoln Park!! Close to Downtown and El
      2 Bedrooms, Sleeps 6
    • Viewed

    Luxury Penthouse Lincoln Park!! Close to Downtown and El

    2 Bedrooms, Sleeps 6
    1. Illinois  >
    2. Chicago Apartment
    #202626vb

    Roscoe Village Guesthouse Lakeview/Roscoe Village, Cubs
      2 Bedrooms, Sleeps 6
    • Viewed

    Roscoe Village Guesthouse Lakeview/Roscoe Village, Cubs

    2 Bedrooms, Sleeps 6
    1. Illinois  >
    2. Chicago Condo
    #262861vb

    Great Location!! Oldtown/Lincolnpark Close to Downtown & El
      2 Bedrooms, Sleeps 18
    • Viewed

    Great Location!! Oldtown/Lincolnpark Close to Downtown & El

    2 Bedrooms, Sleeps 18
    1. Illinois  >
    2. Chicago Apartment
    #202753vb

    Luxury Penthouse Lakeview/Roscoe Village,
      2 Bedrooms,
    • 2 Bathrooms
      • , Sleeps 6
    • Viewed

    Luxury Penthouse Lakeview/Roscoe Village,

    2 Bedrooms,
  • 2 Bathrooms
    • , Sleeps 6
    1. Illinois  >
    2. Chicago Condo
    #228769

    C$231 - C$257
    per night (C$)
    2 - 4 night Minimum Stay
    Grace and Beauty inside and out
      Studio, Sleeps 24
    • Viewed

    Grace and Beauty inside and out

    Studio, Sleeps 24
    1. Illinois  >
    2. Chicago House
    #475707vb

    C$1,232 - C$1,438
    per night (C$)
    3 night Minimum Stay
    Featured - 1,900 Sq Ft - 2 Floors- Jacuzzi - Little Italy
      1 Bedrooms,
    • 1 Bathroom, 
    • 1 Half Bath
      • , Sleeps 4
    • Viewed

    Featured - 1,900 Sq Ft - 2 Floors- Jacuzzi - Little Italy

    1 Bedrooms,
  • 1 Bathroom, 
  • 1 Half Bath
    • , Sleeps 4
    1. Illinois  >
    2. Chicago Condo
    #344019vb

    C$190 - C$231
    per night (C$)
    3 night Minimum Stay
    Charming Executive Condo! Cubs Fun? Close to Wrigley Field.
      1 Bedrooms, Sleeps 4
    • Viewed

    Charming Executive Condo! Cubs Fun? Close to Wrigley Field.

    1 Bedrooms, Sleeps 4
    1. Illinois  >
    2. Chicago Condo
    #263916vb

    C$156 - C$164
    per night (C$)
    3 - 7 night Minimum Stay
    Chicago Luxurious Vintage Condo on the North Shore
      3 Bedrooms,
    • 2 Bathrooms
      • , Sleeps 8
    • Viewed

    Chicago Luxurious Vintage Condo on the North Shore

    3 Bedrooms,
  • 2 Bathrooms
    • , Sleeps 8
    1. Illinois  >
    2. Chicago Condo
    #282600

    Chicago Luxurious Vintage Vacation Condo
      2 Bedrooms,
    • 2 Bathrooms
      • , Sleeps 6
    • Viewed

    Chicago Luxurious Vintage Vacation Condo

    2 Bedrooms,
  • 2 Bathrooms
    • , Sleeps 6
    1. Illinois  >
    2. Chicago Condo
    #285318

    May Specials! Email Now for Incredible Values!
      2 Bedrooms,
    • 2 Bathrooms
      • , Sleeps 6
    • Viewed

    May Specials! Email Now for Incredible Values!

    2 Bedrooms,
  • 2 Bathrooms
    • , Sleeps 6
    1. Illinois  >
    2. Chicago Condo
    #923719

    Landmark Historic 4 Bdrm Home/ Walk to Train Stop for Chicago
      4 Bedrooms,
    • 2 Bathrooms, 
    • 1 Half Bath
      • , Sleeps 12
    • Viewed

    Landmark Historic 4 Bdrm Home/ Walk to Train Stop for Chicago

    4 Bedrooms,
  • 2 Bathrooms, 
  • 1 Half Bath
    • , Sleeps 12
    1. Illinois  >
    2. Chicago House
    #346917vb

    C$354 - C$395
    per night (C$)
    3 night Minimum Stay
    Chicago/Northside by Lake- Mini-Mansion 5 BR/4BA. Sleeps 12-14
      5 Bedrooms,
    • 4 Bathrooms
      • , Sleeps 14
    • Viewed

    Chicago/Northside by Lake- Mini-Mansion 5 BR/4BA. Sleeps 12-14

    5 Bedrooms,
  • 4 Bathrooms
    • , Sleeps 14
    1. Illinois  >
    2. Chicago House
    #470062vb

    C$667 - C$719
    per night (C$)
    2 night Minimum Stay
    Skyline & Lake Views
      3 Bedrooms,
    • 2 Bathrooms, 
    • 1 Half Bath
      • , Sleeps 6
    • Viewed

    Skyline & Lake Views

    3 Bedrooms,
  • 2 Bathrooms, 
  • 1 Half Bath
    • , Sleeps 6
    1. Illinois  >
    2. Chicago Condo
    #394247

    Luxury 2 bedroom on 47th Floor with great views in Magnificent Mile
      2 Bedrooms,
    • 2 Bathrooms
      • , Sleeps 6
    • Viewed

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

    2 Bedrooms,
  • 2 Bathrooms
    • , Sleeps 6
    1. Illinois  >
    2. Chicago Apartment
    #379083

    C$231 - C$477
    per night (C$)
    3 - 7 night Minimum Stay
    1 2 3 4 5 ....8
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