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Chicago Long Term Vacation Rentals(141)

141 Results
$625 - $1,253
per night
3 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 5 night minimum stay
(110)
$260 - $450
per night
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night minimum stay
(188)
$625 - $1,235
per night
3 - 5 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 5 night minimum stay
(47)
$199 - $269
per night
2 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 5 night minimum stay
(27)
  • 2 BR,
  • 1 BA,
  • 2 HF BA,
  • Sleeps 6
3 - 5 night minimum stay
(31)
$550 - $1,110
per night
3 - 5 night minimum stay
  • 2 BR,
  • 3 BA,
  • Sleeps 8
3 - 5 night minimum stay
(49)
  • 3 BR,
  • 1 BA,
  • 2 HF BA,
  • Sleeps 6
2 - 5 night minimum stay
(56)
$550 - $1,110
per night
3 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 7
3 - 5 night minimum stay
(34)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
1 - 3 night minimum stay
(33)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
1 - 3 night minimum stay
(25)
  • 4 BR,
  • 2 BA,
  • Sleeps 9
1 - 3 night minimum stay
(30)
  • 4 BR,
  • 2 BA,
  • Sleeps 9
1 - 3 night minimum stay
(25)
$439
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(62)
$625 - $1,235
per night
3 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 5 night minimum stay
(7)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
6 night minimum stay
(11)
$159 - $199
per night
2 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 5 night minimum stay
(21)
$195 - $250
per night
2 - 3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 - 3 night minimum stay
(7)
$950 - $1,350
per night
2 - 3 night minimum stay
  • 7 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 24
2 - 3 night minimum stay
(14)
$799 - $899
per night
2 - 4 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 4 night minimum stay
2 Reviews
  • 2 BR,
  • 1 BA,
  • Sleeps 22
2 - 30 night minimum stay
1 Review
$300
per night
3 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 8
3 night minimum stay
1 Review
$219 - $299
per night
2 - 3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 7
2 - 3 night minimum stay
(128)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 night minimum stay
1 Review
  • 2 BR,
  • 2 BA,
  • Sleeps 6
(17)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night minimum stay
(4)
  • 4 BR,
  • 4 BA,
  • Sleeps 14
3 night minimum stay
(3)
$159 - $279
per night
3 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 5 night minimum stay
1 Review
  • 2 BR,
  • 2 BA,
  • Sleeps 6
(12)
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Recent Chicago Reviews

Stayed here for last Home Stand!

5 of 5
Best place to stay for Cubs game!!
  • Submitted: Oct 15, 2014
  • Stayed: Sep 2014

Across from Wrigley

5 of 5
Nicer than our own house! Chicago is a great vacation place!
  • Submitted: Oct 15, 2014
  • Stayed: Sep 2014

Johan Basson

5 of 5
Staying at this apartment is like living in a dream. The views are just amazing, the apartment beautiful and the location perfect. We travel very often and we know when you fond a gem and this is most certainly one of the best! Don't even think twice if you are looking at this property, book immediately and enjoy. Thank you so James and Jeri-Lou for an amazing experience. This place was even better than what it looks like on the website!
  • Submitted: Oct 6, 2014
  • Stayed: Oct 2014