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Chicago Vacation Rentals(226)

226 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)
$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
(55)
$225 - $464
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(57)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(58)
  • 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)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(18)
$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)
$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

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

Best place to stay in Chicago

5 of 5
Talk about location! Stayed here for a weekend and it was absolutely wonderful! Close to all that Chicago has to offer, walking distance to all the must-see attractions. So many restaurants that I didn't get a chance try. I'm re-booking for another stay next month for a girls weekend! So much better than a hotel since you get a feel for downtown living. A true gem.
  • Submitted: Oct 11, 2014
  • Stayed: Apr 2014