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Chicago Long Term Vacation Rentals with Online Payment(88)

88 Results
$625 - $1,253
per night
3 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 5 night minimum stay
(115)
$260 - $450
per night
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night minimum stay
(195)
$625 - $1,235
per night
3 - 5 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 5 night minimum stay
(50)
  • 3 BR,
  • 1 BA,
  • 2 HF BA,
  • Sleeps 6
2 - 4 night minimum stay
(57)
$625 - $1,235
per night
3 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 5 night minimum stay
(9)
$195 - $250
per night
2 - 4 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 - 4 night minimum stay
(7)
  • 2 BR,
  • 1 BA,
  • 2 HF BA,
  • Sleeps 6
3 - 4 night minimum stay
(32)
$550 - $1,110
per night
3 - 5 night minimum stay
  • 2 BR,
  • 3 BA,
  • Sleeps 8
3 - 5 night minimum stay
(50)
$450 - $1,110
per night
3 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 7
3 - 5 night minimum stay
(34)
$149 - $199
per night
2 - 4 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 4 night minimum stay
(23)
$199 - $269
per night
2 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 5 night minimum stay
(28)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 night minimum stay
(33)
  • 4 BR,
  • 2 BA,
  • Sleeps 9
3 night minimum stay
(30)
  • 4 BR,
  • 2 BA,
  • Sleeps 9
3 night minimum stay
(25)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
(36)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 5 night minimum stay
(12)
  • 3 BR,
  • 2 BA,
  • Sleeps 10
(10)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 5 night minimum stay
(19)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
6 night minimum stay
(12)
$799 - $899
per night
2 - 4 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 4 night minimum stay
(4)
$135 - $255
per night
3 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 - 5 night minimum stay
(4)
$439
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(63)
$159 - $279
per night
3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
1 Review
$65 - $149
per night
3 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 22
2 - 3 night minimum stay
1 Review
$300
per night
2 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 8
2 night minimum stay
1 Review
  • 2 BR,
  • 2 BA,
  • Sleeps 4
27 - 30 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 10
3 night minimum stay
1 Review
$295 - $450
per night
3 - 4 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 10
3 - 4 night minimum stay
1 Review
$1,225 - $1,400
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 night minimum stay
(5)
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Recent Chicago Reviews

Fantastic place, great value

5 of 5
I have actually rented this property twice, once for a personal trip and once for work. Went to Chicago with a few friends for vacation and had a great time - apartment is amazing and very comfortable. Close to downtown and all the main attractions of Chicago - really well laid out and nice features like the luxury bathroom, fireplace and big kitchen. Fast internet, lots of workspace to get other things done as well. Quiet and cozy and met all of my needs. I couldn't have been happier with my choice and will definitely stay here again when I'm back in Chicago.
  • Submitted: Dec 16, 2014
  • Stayed: Nov 2014

GREAT Penthouse

5 of 5
NICE condo. Really wonderful two story windows and wrap around balcony to enjoy the penthouse views. Great location. Lots of amenities. Thank you - We enjoyed our stay very much!
  • Submitted: Dec 9, 2014
  • Stayed: Jun 2014

Great Place to stay

5 of 5
This is my second stay with Dexter and Tiffany. They are fantastic hosts. The place is wonderful and always clean. I will be staying again. I highly recommend this house for a comfortable and clean place to stay!! I also love that they have wireless and the TV has access to Netflix.
  • Submitted: Nov 23, 2014
  • Stayed: Nov 2014