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Chicago Vacation Rentals(118)

118 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)
$415 - $875
per night
3 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 5 night minimum stay
(105)
$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)
$225 - $464
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(58)
$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)
$550 - $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)
$260 - $450
per night
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night minimum stay
(9)
$199 - $269
per night
2 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 5 night minimum stay
(28)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 24
2 - 4 night minimum stay
(34)
  • 4 BR,
  • 2 BA,
  • Sleeps 9
3 night minimum stay
(25)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(57)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(35)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(58)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(18)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night minimum stay
(14)
$225 - $464
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(5)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
(36)
$775 - $825
per night
3 - 4 night minimum stay
  • 5 BR,
  • 5 BA,
  • Sleeps 14
3 - 4 night minimum stay
(5)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 5 night minimum stay
(12)
$225 - $464
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(4)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
(63)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 night minimum stay
(33)
  • 4 BR,
  • 2 BA,
  • Sleeps 9
3 night minimum stay
(30)
  • 3 BR,
  • 2 BA,
  • Sleeps 10
(10)
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Recent Chicago Reviews

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

WOW! Spacious, Clean Condo! Amazing Views, Great Location & Walking Distance to Mag Mile Shopping!

5 of 5
We just got home from staying in a condo on the 35th floor of The Grand Plaza. (both units are similar, managed by the same company). I can't say enough good about the condo and the company that manages it! It was very clean, very spacious, very nice with great views from the balcony of The Hancock Building. The shower was wonderful, towels were thick and nice, & the beds very comfortable! It was quiet and had black out shades in the bedroom so it was dark for good, restful sleep after a busy day in the city. It was exactly as advertised. It is perfect for tourists! It is walking distance to great shopping and dining on the Magnificent Mile, Water Tower Place etc. It was super convenient to have a grocery store on the first floor of the building and parking in the building. (Parking was included which was nice). The managers were kind, efficient and helpful even allowing us to keep our car parked in the building after check out. I would highly recommend this unit and would definitely stay here again. Thank you for a great stay in Chicago! :)
  • Submitted: Nov 19, 2014
  • Stayed: Nov 2014