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Chicago Vacation Rentals with Online Booking(156)

156 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)
  • 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
(57)
  • 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)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
1 - 3 night minimum stay
(25)
$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)
$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)
$225 - $464
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(5)
$139 - $249
per night
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night minimum stay
(6)
$225 - $464
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(4)
$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)
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Recent Chicago Reviews

Everything we wanted and more!

5 of 5
This was our first trip with our 14 & 11 yr old to Chicago so we wanted to have the convenience of being able to walk to everything, and still have a comfortable place to rest. This fit the bill! The condo was very clean, very comfortable, and the views were spectacular. I even got a GREAT shot of the sunset. The beds were comfortable. The kitchen was spacious & had anything we needed for utensils. We watched the Chicago Marathon runners from every window. The entire process was painless, from prompt communication, booking, directions, and the app they have was awesome for checking in and out. We'd love to stay here again sometime!
  • Submitted: Oct 15, 2014
  • Stayed: Oct 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

Chicago Getaway

5 of 5
My wife and I stayed in this 45th fl. apartment on our quick trip to Chicago. Everything was perfect.....easy check-in, great location, spacious and very clean apartment, terrific view, complete services and adjacent food store. Communication with Premier Suites was very responsive and professional. I highly recommend this unit to everyone.
  • Submitted: Oct 8, 2014
  • Stayed: Sep 2014