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Chicago Vacation Rentals with Online Payment(155)

155 Results
$625 - $1,253
per night
3 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 5 night minimum stay
(115)
$260 - $450
per night
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night minimum stay
(195)
$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
(50)
  • 3 BR,
  • 1 BA,
  • 2 HF BA,
  • Sleeps 6
2 - 4 night minimum stay
(57)
$625 - $1,235
per night
3 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 5 night minimum stay
(10)
  • 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)
$149 - $199
per night
2 - 4 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 4 night minimum stay
(23)
$260 - $450
per night
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night minimum stay
(9)
$199 - $269
per night
2 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 5 night minimum stay
(28)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 24
2 - 4 night minimum stay
(34)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night minimum stay
(14)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
(36)
$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 8
2 night minimum stay
(63)
  • 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)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 3 night minimum stay
(78)
$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
6 night minimum stay
(12)
$799 - $899
per night
2 - 4 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 4 night minimum stay
(4)
$439
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(63)
$250 - $400
per night
2 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 night minimum stay
1 Review
$300
per night
2 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 8
2 night minimum stay
1 Review
  • 2 BR,
  • 1 BA,
  • Sleeps 22
2 - 3 night minimum stay
1 Review
$139 - $249
per night
3 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 night minimum stay
(6)
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Recent Chicago Reviews

Perfection!!!

5 of 5
Our stay in this condo was pure perfection!!! It's a beautiful condo, well-maintained, very clean, well-stocked, and a perfect location. The owners were easy to work with and quick to respond. It was a perfect location for us to celebrate a 65th birthday & Christmas in the same weekend. We can't say enough about how much we loved our stay!!!
  • Submitted: Dec 23, 2014
  • Stayed: Dec 2014

Great location. Clean. Awesome amenities!

5 of 5
My husband and I stayed at Sarah's place this past weekend. Communication was great and the property was clean and well stocked with everything we needed. I am coming back to Chicago next month for a conference and plan on staying at Sarah's place again.
  • Submitted: Dec 13, 2014
  • Stayed: Dec 2014

Great Location for shopping, dining, lake/beach

5 of 5
This is a great brownstone for a small group or family size of 4-6. The location is great, tucked between great restaurants and fun bars on Division St. or tons of shopping on Michigan Ave. The lake is within walking distance as well. It is safe and the street is adorable. My girlfriends and I do a annual shopping trip to Chicago and we've stayed here twice. We will be back.
  • Submitted: Nov 13, 2014
  • Stayed: Oct 2014