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Chicago Vacation Rentals with Online Payment(162)

162 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
(59)
$625 - $1,235
per night
3 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 5 night minimum stay
(11)
  • 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,
  • 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)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night minimum stay
(19)
$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 8
2 night minimum stay
(64)
$775 - $825
per night
3 - 4 night minimum stay
  • 5 BR,
  • 5 BA,
  • Sleeps 14
3 - 4 night minimum stay
(5)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 5 night minimum stay
(12)
  • 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)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 night minimum stay
(16)
$799 - $899
per night
2 - 4 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 4 night minimum stay
(4)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 3 night minimum stay
(80)
$750 - $1,375
per night
2 - 3 night minimum stay
  • 6 BR,
  • 5 BA,
  • Sleeps 11
2 - 3 night minimum stay
(20)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
4 - 5 night minimum stay
(12)
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 14
2 night minimum stay
(3)
$139 - $249
per night
3 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 night minimum stay
(6)
$439
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(64)
  • 2 BR,
  • 1 BA,
  • Sleeps 22
2 - 3 night minimum stay
2 Reviews
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Recent Chicago Reviews

Perfect for McCormick Show

5 of 5
This property was perfect for our team working a show at McCormick Center. It was clean, well equipped, and ready when we arrived. The hot tub certainly was nice after being on our feet all day. The bonus for us was the neighborhood restaurants. I had no idea that Bridgeport would deliver such convenience and choices to fill up after working all day. Great place and location. We are booking next year now.
  • Submitted: Jan 26, 2015
  • Stayed: Jan 2015

Very impressed with our stay. I would recommend this place to anyone visiting Chicago.

5 of 5
We were in Chicago this past week for a wedding and stayed at Sarah's place. This location is amazing. The building is new and we had everything we needed.
  • Submitted: Jan 23, 2015
  • Stayed: Jan 2015

New Year's Celebration

5 of 5
What a view! Beautiful place - convenient to everything - owners are fantastic with communication and promptness. We will be back again. Grocery store right downstairs, a Whole Foods a few blocks away made cooking dinner easy - and eating at the table with that view with the fireplace going was the best. Thank you!
  • Submitted: Jan 6, 2015
  • Stayed: Dec 2014