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Chicago Vacation Rentals(223)

223 Results
$260 - $450
per night
3 - 5 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night min stay
(199)
$415 - $875
per night
3 - 5 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 5 night min stay
(105)
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 4 night min stay
(60)
  • 2 BR,
  • 1 BA,
  • Sleeps 7
2 - 3 night min stay
(134)
$625 - $1,235
per night
3 - 5 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 5 night min stay
(13)
$625 - $1,253
per night
3 - 5 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 5 night min stay
(116)
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
3 - 4 night min stay
(32)
  • 6 BR,
  • 5 BA,
  • Sleeps 11
2 - 3 night min stay
(20)
$260 - $450
per night
3 - 5 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night min stay
(13)
$550 - $1,110
per night
3 - 5 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 7
3 - 5 night min stay
(35)
$169 - $199
per night
2 - 4 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 4 night min stay
(23)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 24
1 - 4 night min stay
(39)
$625 - $1,235
per night
3 - 5 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 5 night min stay
(53)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night min stay
(29)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 night min stay
(25)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
2 night min stay
(64)
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 14
2 night min stay
(7)
$199 - $269
per night
2 - 5 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 5 night min stay
(30)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 night min stay
(38)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 4 night min stay
(20)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 5 night min stay
(12)
$775 - $825
per night
3 - 4 night min stay
  • 5 BR,
  • 5 BA,
  • Sleeps 14
3 - 4 night min stay
(5)
$799 - $899
per night
2 - 4 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 4 night min stay
(4)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
2 night min stay
(9)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
4 - 5 night min stay
(14)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 night min stay
(6)
$439
per night
3 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night min stay
(65)
  • 2 BR,
  • 2 BA,
  • Sleeps 14
(5)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
(7)
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Recent Chicago Reviews

Spectacular Chicago penthouse

5 of 5
We used this property to celebrate our parents 50th wedding anniversary. The accommodations were very comfortable, spacious and extremely well maintained. The property also had little extras (spices, cling wrap etc) which made cooking during our stay easier and more enjoyable. The information provided by our hosts and the interactions with them were excellent. The location is second to none for a downtown Chicago experience and is conveniently located by many restaurants, stores (shops and grocery) and was close to points of interest or close to public transportation options to go wherever we wanted. A car truly is not needed to take full advantage of the property. We travel to chicago annually and will consider this property for our next trip. We would Highly recommend this property to fily or friends.
  • Submitted: Mar 28, 2015
  • Stayed: Mar 2015

Perfect location, clean, and awesome owners !

5 of 5
Wonderful house in a nice neighborhood. Situated very close to everything you'd want to do in and around the greater Chicago area. Owner is very personable and ensured our comfort and needs were met. Very well kept home with upgrades and amenities rarely experienced :) Jacuzzi was very clean and ready, garage space provided. We have definitely found a permanent place to stay when we go back!
  • Submitted: Mar 27, 2015
  • Stayed: Mar 2015

Great Location!

5 of 5
We enjoyed our stay in Chicago and would definitely recommend this property. The location was perfect. The property was very clean and worked perfectly for 2 couples. Check-in was a little clunky, but communication was good. It would have been nice to have one more comfortable chair in the living area. The view was wonderful through all the floor to ceiling windows. The fitness room was spacious and well equipped. We appreciated the manager's suggestion about Uber. Overall this was a great property!
  • Submitted: Mar 26, 2015
  • Stayed: Mar 2015