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Chicago Vacation Rentals with Air Conditioning(275)

275 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
(189)
$415 - $875
per night
3 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 5 night minimum stay
(103)
$625 - $1,235
per night
3 - 5 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 5 night minimum stay
(47)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
(61)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(58)
$225 - $464
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(58)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(55)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(35)
$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)
  • 2 BR,
  • 1 BA,
  • Sleeps 4
4 night minimum stay
(42)
$550 - $1,110
per night
3 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 7
3 - 5 night minimum stay
(34)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(18)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 night minimum stay
(33)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 night minimum stay
(25)
  • 4 BR,
  • 2 BA,
  • Sleeps 9
3 night minimum stay
(30)
  • 4 BR,
  • 2 BA,
  • Sleeps 9
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)
$270 - $400
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(11)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
6 night minimum stay
(11)
$260 - $450
per night
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night minimum stay
(7)
  • 5 BR,
  • 3 BA,
  • Sleeps 13
3 night minimum stay
(29)
$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)
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Recent Chicago Reviews

Week of Vacation in Chicago

5 of 5
After three of our kids got married this past summer my wife and I wanted to get away for a week and just relax! What a great week we had!! This specific Condo is even nicer than it shows online! Beautiful city views, great location for shopping and restaurants! The Condo was clean, well decorated and updated with appliances and furniture that match the beautiful location. I would recommend this unit for future stays in this wonderful city! Thank You Premier Suites for following through on everything you promised!
  • Submitted: Oct 21, 2014
  • Stayed: Oct 2014

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