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Chicago Vacation Rentals(235)

235 Results
$475 - $1,253
per night
3 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 5 night minimum stay
(113)
$475 - $1,235
per night
3 - 5 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 5 night minimum stay
(48)
$450 - $1,110
per night
3 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 7
3 - 5 night minimum stay
(34)
  • 2 BR,
  • 1 BA,
  • 2 HF BA,
  • Sleeps 6
3 - 5 night minimum stay
(32)
$199 - $269
per night
2 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 5 night minimum stay
(27)
  • 3 BR,
  • 1 BA,
  • 2 HF BA,
  • Sleeps 6
2 - 5 night minimum stay
(57)
$149 - $199
per night
2 - 4 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 4 night minimum stay
(23)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night minimum stay
(9)
$270 - $400
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(14)
$475 - $1,235
per night
3 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 5 night minimum stay
(7)
  • 2 BR,
  • 1 BA,
  • Sleeps 4
4 night minimum stay
(44)
$750 - $1,375
per night
2 - 3 night minimum stay
  • 6 BR,
  • 5 BA,
  • Sleeps 11
2 - 3 night minimum stay
(20)
$335 - $460
per night
2 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
(9)
$799 - $899
per night
2 - 4 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 4 night minimum stay
(4)
$260 - $450
per night
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night minimum stay
(193)
$415 - $875
per night
3 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 5 night minimum stay
(104)
$750 - $825
per night
3 - 4 night minimum stay
  • 5 BR,
  • 5 BA,
  • Sleeps 14
3 - 4 night minimum stay
(3)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 night minimum stay
(7)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 3 night minimum stay
(78)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
6 night minimum stay
(12)
$439
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(63)
$260 - $450
per night
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night minimum stay
(7)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
(63)
  • 2 BR,
  • 1 BA,
  • Sleeps 22
2 - 30 night minimum stay
1 Review
  • 2 BR,
  • 2 BA,
  • Sleeps 14
(5)
$139 - $249
per night
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night minimum stay
(6)
$300 - $400
per night
1 - 2 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 12
1 - 2 night minimum stay
(29)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 5 night minimum stay
(43)
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 14
2 night minimum stay
1 Review
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Recent Chicago Reviews

Charming Chicago

5 of 5
We were delighted to find this apartment for the time that we were visiting our son and his family -- welcoming our third granddaughter born the day we arrived. The apartment was only a short walk from their condo. My husband went out every morning for coffee at Starbucks and The Grind, which are literally around the block. The living room is very comfortable and beautifully decorated. The bedroom was spacious and the bed was very comfortable. Although we did not cook while there, the kitchen had everything that one would need. Carl has thought of EVERY detail and is such a welcoming host. He worked with our arrival schedule and emailed us during the stay to see if we needed anything. We will be staying again in future visits and would highly recommend this charming apartment to anyone.
  • Submitted: Nov 19, 2014
  • Stayed: Nov 2014

Great apartment

5 of 5
We spend our vacation in Chicago visiting or daughter, and we really enjoyed the apartment. Ned was very professional, everything was as it should be, good heater, very clean, everything very convenient. And very, very nice apartment. Absolutly recomend
  • Submitted: Nov 18, 2014
  • Stayed: Nov 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