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Save time when booking: choose rentals that accept online reservations or online payments

Chicago with Online Payment(211)

211 Results
$625 - $1,253
per night
3 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 5 night minimum stay
(116)
$260 - $450
per night
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night minimum stay
(196)
$415 - $875
per night
3 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 5 night minimum stay
(105)
$625 - $1,235
per night
3 - 5 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 5 night minimum stay
(52)
  • 3 BR,
  • 1 BA,
  • 2 HF BA,
  • Sleeps 6
2 - 4 night minimum stay
(58)
$625 - $1,235
per night
3 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 5 night minimum stay
(11)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(60)
$195 - $250
per night
2 - 4 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 - 4 night minimum stay
(7)
  • 2 BR,
  • 1 BA,
  • 2 HF BA,
  • Sleeps 6
3 - 4 night minimum stay
(32)
$550 - $1,110
per night
3 - 5 night minimum stay
  • 2 BR,
  • 3 BA,
  • Sleeps 8
3 - 5 night minimum stay
(51)
$550 - $1,110
per night
3 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 7
3 - 5 night minimum stay
(34)
$260 - $450
per night
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night minimum stay
(10)
$185 - $269
per night
2 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 5 night minimum stay
(29)
$149 - $199
per night
2 - 4 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 4 night minimum stay
(23)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 24
2 - 4 night minimum stay
(37)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(36)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(58)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(64)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(24)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night minimum stay
(18)
$169 - $925
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(7)
$165 - $300
per night
2 - 4 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 6
2 - 4 night minimum stay
(5)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 5 night minimum stay
(12)
$225 - $925
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(4)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
(64)
  • 3 BR,
  • 2 BA,
  • Sleeps 10
(10)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 5 night minimum stay
(19)
$335 - $460
per night
2 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
(9)
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Recent Chicago Reviews

Amazing Location - Chicago Short term Condo Rental

5 of 5
We stayed in Chicago for three weeks in a two bedroom condo on State and Ohio over Christmas 2014 because our son was getting married. It was a wonderful experience for us. The condo was exceptionally comfortable and nicely furnished with many extra touches. We were able to have a few friends who were in town for the wedding stop over for a cozy visit. The was beautifully and tastefully decorated. More importantly, the front desk was very friendly and helpful to us. I don't think we could have chosen a more convenient location than this! Easy walk to Magnificent Mile, many fine restaurants nearby, and a large Osco Jewell grocery store attached to the condo. We certainly made use of the exercise facilities as well! Chicago Premier Suites were easy, professional, and efficient in helping us make our reservation. Their follow up with a few additional needs was personal and appreciated. Because our newlyweds will be living in Chicago, we will likely repeat this experience. SO MUCH MORE COMFORTABLE THAN A HOTEL. We needed a car, and parking was included and convenient.
  • Submitted: Jan 24, 2015
  • Stayed: Dec 2014

Great place for 2 couples to enjoy a long weekend in Chicago

5 of 5
This high rise unit had spectacular views from a large balcony that we thoroughly enjoyed! The unit was very clean and centrally located so we could easily walk to most of the places we wanted to go. We also used the smart phone app sent by the property owner/manager and it made finding the place and checking in very easy. We had a car so we arranged for parking with the unit and so we had no problems with having to leave bags somewhere before or after checkin/out.
  • Submitted: Jan 21, 2015
  • Stayed: Oct 2014

Enjoyable Stay

5 of 5
We are sitting at the gate in Chicago O'Hare, ready to go home after a very nice stay in the city of Chicago, made even more enjoyable after having stayed at the Grand Plaza. Thank you so much for having accommodated us. We found everything clean, neat and in perfect condition. Hope we left everything in order as well!! Next time we travel to Chicago, I'll be sure to contact you with enough time in advance so as to be able to find space with you. Thank you again, and until the next time...!!
  • Submitted: Jan 21, 2015
  • Stayed: Nov 2014