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Chicago Vacation Rentals for Golf Vacations

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SPECIAL OFFER! Save 15% in April April 5 - April 30

Chicago Beautiful and Luxurious 3 Bedroom / 2 Bathroom Chicago Vacation Rental

  • 3 BR/2 BA Condo (sleeps 8)
    $250 - $360/nt
    $1,830 - $2,340/wk
    $7,500 - $8,700/month
    per property, wheelchair accessible, Downtown, Lake, Jacuzzi, Balcony, Air Conditioning, Internet, Satellite / Cable, Television
SPECIAL OFFER! Save 15% in April April 5 - April 30

Chicago Beautiful and Luxurious Andersonville 2 BR /2 BA

  • 2 BR/2 BA Condo (sleeps 6)
    $220 - $300/nt
    $1,980/wk
    $5,200 - $7,800/month
    per property, accept credit card, wheelchair accessible, Beach, Downtown, terrace, Balcony, Air Conditioning, Internet, Satellite / Cable

Chicago Luxury Studio, Steps To Everything

  • 1 BR1 BA Studio (sleeps 3)
    $150 - $185/nt
    per property, Hot Tub, wheelchair accessible, Downtown, Communal Pool, Sauna, Fitness Room / Equipment, Air Conditioning, Internet

Chicago Luxury Resort in the Heart of Downtown Chicago

  • 2 BR/2 BA Apartment (sleeps 6)
    $429/nt
    per property, accept credit card, Hot Tub, Downtown, Resort, Communal Pool, Jacuzzi, Sauna, Tennis Court, Lawn / Garden

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

  • 2 BR/2 BA Apartment (sleeps 6)
    $225 - $464/nt
    $1,675 - $3,358/wk
    $6,490 - $11,850/month
    per property, Hot Tub, Downtown, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, DVD Player

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

  • 2 BR/2 BA Condo (sleeps 6)
    $225 - $464/nt
    $1,675 - $3,358/wk
    $6,490 - $11,850/month
    per property, Hot Tub, Beach, Downtown, Lake, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, DVD Player

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

  • 2 BR/2 BA Apartment (sleeps 6)
    $225 - $464/nt
    $1,675 - $3,358/wk
    $6,490 - $11,850/month
    per property, Downtown, Lake, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, DVD Player

Chicago Magnificent Mile Luxury Corner Unit on 45th Floor with great views

  • 2 BR/2 BA Apartment (sleeps 6)
    $225 - $464/nt
    $1,675 - $3,358/wk
    $6,490 - $11,850/month
    per property, Hot Tub, Downtown, Lake, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, DVD Player

Chicago Condo in Hot Bucktown / Wicker Park Neighborhood

  • 2 BR/2 BA Condo (sleeps 4)
    $175 - $334/nt
    $1,325 - $2,422/wk
    $5,170 - $8,570/month
    per property, pets considered, Downtown, Balcony, Air Conditioning, Internet, Satellite / Cable, DVD Player, Fireplace

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

  • 2 BR/2 BA Apartment (sleeps 6)
    $225 - $464/nt
    $1,675 - $3,358/wk
    $6,490 - $11,850/month
    per property, Hot Tub, Downtown, Lake, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, DVD Player

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

  • 4 BR/2 BA, 1 half bath House (sleeps 9)
    $850 - $1,200/nt
    $7,500/wk
    per property, accept credit card, Downtown, Lawn / Garden, Balcony, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable

Chicago Lake Front Mansion Perfect For Your Family Reunion Or Corporate Retreat

  • 7 BR/6 BA, 1 half bath House (sleeps 24)
    $1,350/nt
    $7,500/wk
    $25,000/month
    per property, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television, Parking, Fireplace

Chicago Value and Luxury. Close to City and McCormick Place. Skyline View and Hot Tub

  • 3 BR/1 BA, 1 half bath Apartment (sleeps 6)
    $110 - $255/nt
    $875 - $1,650/wk
    per property, accept credit card, Hot Tub, Town, Sauna, Air Conditioning, Internet, Satellite / Cable, Television

Chicago Luxury and Value Close to Everything and McCormick Place Skyline View, Hot Tub

  • 2 BR/1 BA, 1 half bath Apartment (sleeps 6)
    $110 - $255/nt
    $875 - $1,650/wk
    per property, accept credit card, Hot Tub, Downtown, Town, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Chicago Magnificent Mile luxury High Rise on 43rd floor with great views

  • 2 BR/2 BA Apartment (sleeps 6)
    $225 - $464/nt
    $1,675 - $3,358/wk
    $6,490 - $11,850/month
    per property, pets considered, Hot Tub, Downtown, Lake, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable

Chicago Great views-Luxury 2 bedroom on 32nd Floor Magnificent Mile

  • 2 BR/2 BA Apartment (sleeps 6)
    $225 - $464/nt
    $1,675 - $3,358/wk
    $6,490 - $11,850/month
    per property, Hot Tub, Beach, Downtown, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, DVD Player

Chicago Teri's Chicago Guest House * Wrigley Suite * Wrigleyville

  • 4 BR/2 BA Apartment (sleeps 8)
    $499/nt
    $2,795/wk
    per property, accept credit card, Downtown, Lake, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Chicago Your Sweet Chicago Home

  • 6 BR/3 BA Apartment (sleeps 14)
    $900/nt
    per property, pets considered, Hot Tub, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Chicago Urban Luxury Home In Downtown Chicago!

  • 3 BR/3 BA House (sleeps 11)
    $295/nt
    per property, Hot Tub, Downtown, Sauna, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Chicago Downtown Urban Oasis! Near Transit, Sites, Nightlife -- Huge Deck + Parking!

  • 3 BR/2 BA House (sleeps 8)
    $275 - $295/nt
    per property, Hot Tub, Downtown, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, Parking

Chicago Featured On Travel Chanel With Views Of Wrigley Field, Beautiful New 4 Bedroom

  • 4 BR/2 BA Condo (sleeps 9)
    $429 - $459/nt
    per property, Village, Air Conditioning, Internet, Satellite / Cable, Television, Parking, Fireplace

Chicago Fabulous Lincoln Park Apartment near DePaul Univ; Only Owner Managed

  • 3 BR/2 BA Condo (sleeps 8)
    $265 - $300/nt
    $1,879 - $2,005/wk
    $6,100 - $8,190/month
    per property, accept credit card, Downtown, Lake, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Chicago Beautiful 2 Bedroom, 2 Bath Chicago Vacation Rental Condo

  • 2 BR/2 BA Condo (sleeps 6)
    $180 - $280/nt
    $1,340 - $1,840/wk
    $5,400 - $7,200/month
    per property, accept credit card, wheelchair accessible, Downtown, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Chicago Spacious 2 bed, 2 bath luxury apartment close to Mag Mile.

  • 2 BR/2 BA Condo (sleeps 4)
    $1,400/wk
    $4,050/month
    per property, accept credit card, pets considered, Beach, Downtown, Lake, Jacuzzi, Balcony, Air Conditioning, Internet, Satellite / Cable

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

  • 3 BR/1 BA Apartment (sleeps 6)
    $225/nt
    $1,500/wk
    per property, accept credit card, Downtown, Lake, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

Chicago Across From Wrigley Field, Beautiful New 4 Bedroom Featured On Travel Channel!

  • 4 BR/2 BA Condo (sleeps 9)
    $429 - $459/nt
    per property, Village, Air Conditioning, Internet, Satellite / Cable, Television, Parking, Fireplace

Chicago Teri's Chicago Guest House *Clark Suite * Wrigleyville

  • 3 BR/2 BA Apartment (sleeps 8)
    $459/nt
    $2,571/wk
    per property, accept credit card, Downtown, Lake, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Chicago Lakeshore, Millennium Park High Rise

  • 2 BR/2 BA Condo (sleeps 6)
    $100/nt
    per property, accept credit card, wheelchair accessible, Downtown, Waterfront, terrace, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable

Chicago Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment

  • 2 BR/1 BA Apartment (sleeps 6)
    $195 - $250/nt
    $950 - $1,450/wk
    $2,450 - $4,500/month
    per property, accept credit card, pets considered, Downtown, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television

Chicago Wonderful Lincoln Park/DePaul Apartment In A Great Location,Only Owner Managed

  • 3 BR/2 BA Condo (sleeps 8)
    $265 - $300/nt
    $1,844 - $2,040/wk
    $6,800 - $7,740/month
    per property, accept credit card, Downtown, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television, Parking

Chicago Downtown Chicago Luxury Home - Elegance, Comfort, Convenience

  • 4 BR/4 BA House (sleeps 11)
    $600 - $850/nt
    $4,900/wk
    per property, accept credit card, Downtown, Lake, Jacuzzi, terrace, Balcony, Fitness Room / Equipment, Air Conditioning, Internet

Chicago Teri's Chicago Guest House * Shoreline Suite * Wrigleyville

  • 3 BR/2 BA Apartment (sleeps 6)
    $389/nt
    $2,179/wk
    per property, accept credit card, Downtown, Lake, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Chicago Beautiful New 3 Bedroom Featured On Travel Channel, Across From Wrigley Field!

  • 3 BR/2 BA Condo (sleeps 8)
    $329 - $359/nt
    per property, Village, Air Conditioning, Internet, Satellite / Cable, Television, Parking, Fireplace

Chicago Walk or Easy Access to Transit... 3 Bedroom...Sleeps 5

  • 3 BR/1 BA Apartment (sleeps 5)
    $225 - $285/nt
    per property, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Chicago Fantastic Downtown Chicago Condo

  • 2 BR/2 BA Condo (sleeps 5)
    $180 - $200/nt
    $1,260 - $1,400/wk
    $5,010 - $5,040/month
    per property, pets considered, wheelchair accessible, Beach, Downtown, Lake, River, Waterfront, Jacuzzi, Sauna, Balcony, Fitness Room / Equipment, Air Conditioning

Chicago Beautiful River North Chicago Condo

  • 1 BR/1 BA Condo (sleeps 3)
    $130 - $180/nt
    $910/wk
    $3,810 - $4,200/month
    per property, pets considered, Hot Tub, wheelchair accessible, Beach, Downtown, Lake, River, Waterfront, Communal Pool, Sauna, Balcony, Fitness Room / Equipment

Chicago Fantastic Downtown Chicago Condo

  • 1 BR/1 BA Condo (sleeps 3)
    $130 - $150/nt
    $910 - $1,050/wk
    $3,556 - $4,020/month
    per property, accept credit card, pets considered, wheelchair accessible, Beach, Downtown, Lake, River, Waterfront, Jacuzzi, Sauna, Balcony, Fitness Room / Equipment

Chicago Luxury1 or 2 Bedroom Apts in Lincoln Park/N Lakeview Area,Wi-Fi, vintage beauty

  • 3 BR/3 BA Condo (sleeps 3)
    $1,975/month
    Lake, Town, Tennis Court, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Chicago Stop Searching! Chicago's Most Exclusive & Luxurious Residence

  • 2 BR/2 BA Apartment (sleeps 6) Hot Tub, wheelchair accessible, Downtown, Jacuzzi, Sauna, terrace, Balcony, Fitness Room / Equipment

Chicago Classic 3 Bedroom Victorian Greystone in Chicago's Wrigleyville!

  • 3 BR/1 BA Apartment (sleeps 6) accept credit card, Downtown, Lake, Balcony, Air Conditioning, Internet, Television, DVD Player

Chicago Brand New Construction Guesthouse, Fully-Furnished, Upscale, Elegant, Modern,

  • 1 BR/1 BA Apartment (sleeps 4) accept credit card, wheelchair accessible, Downtown, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

Chicago Cozy home away from home located 25 minutes from downtown Chicago

  • 2 BR/1 BA House (sleeps 6)
    $125 - $145/nt
    $775/wk
    $1,750/month
    per property, accept credit card, Air Conditioning, Internet, Television, DVD Player

Chicago Wake to Sunrise Over Lake Michigan! Spacious with Stunning Views!

  • 1 BR/1 BA Condo (sleeps 4)
    $175 - $225/nt
    $1,150 - $1,400/wk
    per property, wheelchair accessible, Communal Pool, Sauna, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable, Television

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

  • 2 BR/2 BA Condo (sleeps 4)
    $3,547 - $3,733/month
    per property, wheelchair accessible, Downtown, Lake, Balcony, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable, Television

Chicago Convenience Is Key... Just 2 Blocks To The Brown Line 'L'!

  • 3 BR/1 BA Apartment (sleeps 5)
    $265/nt
    per property, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

Chicago The North Side Suites - 4 Bedroom - blocks from Magnificent Mile,

  • 4 BR/2 BA Apartment (sleeps 10)
    $375/nt
    per property, accept credit card, Hot Tub, Downtown, Lake, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Chicago A Classical Home In The Heart Of Chicago With Few Minute Walk To Lincoln Park

  • 4 BR/3 BA House (sleeps 8)
    $465/nt
    $2,800/wk
    per property, Downtown, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

Chicago Lovely Streeterville Apartment

  • 1 BR/1 BA Apartment (sleeps 3)
    $140/nt
    $980/wk
    $3,810/month
    per property, pets considered, Hot Tub, wheelchair accessible, Beach, Downtown, Lake, River, Waterfront, Communal Pool, Sauna, Balcony, Fitness Room / Equipment

Chicago Penthouse Views!

  • 1 BR/1 BA Condo (sleeps 4)
    $125 - $200/nt
    $800 - $1,300/wk
    $3,000 - $4,000/month
    per property, accept credit card, pets considered, Beach, Downtown, Lake, Waterfront, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Chicago Lincoln Park Suite - 4 Bed, 2 Bath - Sleeps 8

  • 4 BR/2 BA Apartment (sleeps 10)
    $4,980/month
    per property, Downtown, Lake, Air Conditioning, Internet, Satellite / Cable, DVD Player
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