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Chicago Vacation Rentals with Online Booking(154)

154 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)
$195 - $250
per night
2 - 3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 - 3 night minimum stay
(7)
$450 - $1,110
per night
3 - 5 night minimum stay
  • 2 BR,
  • 3 BA,
  • Sleeps 8
3 - 5 night minimum stay
(50)
$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)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 night minimum stay
(33)
  • 4 BR,
  • 2 BA,
  • Sleeps 9
3 night minimum stay
(30)
  • 4 BR,
  • 2 BA,
  • Sleeps 9
3 night minimum stay
(25)
$199 - $269
per night
2 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 5 night minimum stay
(27)
$225 - $464
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(58)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(57)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(35)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(58)
  • 3 BR,
  • 1 BA,
  • 2 HF BA,
  • Sleeps 6
2 - 5 night minimum stay
(57)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(18)
$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)
$225 - $464
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(5)
$225 - $464
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(4)
  • 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)
  • 3 BR,
  • 2 BA,
  • Sleeps 10
(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)
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Recent Chicago Reviews

WOW! Spacious, Clean Condo! Amazing Views, Great Location & Walking Distance to Mag Mile Shopping!

5 of 5
We just got home from staying in a condo on the 35th floor of The Grand Plaza. (both units are similar, managed by the same company). I can't say enough good about the condo and the company that manages it! It was very clean, very spacious, very nice with great views from the balcony of The Hancock Building. The shower was wonderful, towels were thick and nice, & the beds very comfortable! It was quiet and had black out shades in the bedroom so it was dark for good, restful sleep after a busy day in the city. It was exactly as advertised. It is perfect for tourists! It is walking distance to great shopping and dining on the Magnificent Mile, Water Tower Place etc. It was super convenient to have a grocery store on the first floor of the building and parking in the building. (Parking was included which was nice). The managers were kind, efficient and helpful even allowing us to keep our car parked in the building after check out. I would highly recommend this unit and would definitely stay here again. Thank you for a great stay in Chicago! :)
  • Submitted: Nov 19, 2014
  • Stayed: Nov 2014

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