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Chicago Long Term Vacation Rentals(128)

128 Results
$475 - $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)
$475 - $1,235
per night
3 - 5 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 5 night minimum stay
(49)
$140 - $230
per night
2 - 4 night minimum stay
  • 3 BR,
  • 1 BA,
  • 2 HF BA,
  • Sleeps 6
2 - 4 night minimum stay
(57)
$475 - $1,235
per night
3 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 5 night minimum stay
(9)
$195 - $250
per night
2 - 3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 - 3 night minimum stay
(7)
$140 - $225
per night
3 - 4 night minimum stay
  • 2 BR,
  • 1 BA,
  • 2 HF BA,
  • Sleeps 6
3 - 4 night minimum stay
(32)
$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)
$149 - $199
per night
2 - 4 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 4 night minimum stay
(23)
$199 - $269
per night
2 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 5 night minimum stay
(28)
  • 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)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
(36)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 5 night minimum stay
(12)
  • 3 BR,
  • 2 BA,
  • Sleeps 10
(10)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 5 night minimum stay
(19)
$799 - $899
per night
2 - 4 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 4 night minimum stay
(4)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
6 night minimum stay
(12)
$135 - $255
per night
3 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 - 5 night minimum stay
(4)
$439
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(63)
$159 - $279
per night
3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
1 Review
$65 - $149
per night
3 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 22
2 - 3 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,
  • 2 BA,
  • Sleeps 14
(5)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
(7)
  • 4 BR,
  • 2 BA,
  • Sleeps 10
1 Review
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Recent Chicago Reviews

GREAT Penthouse

5 of 5
NICE condo. Really wonderful two story windows and wrap around balcony to enjoy the penthouse views. Great location. Lots of amenities. Thank you - We enjoyed our stay very much!
  • Submitted: Dec 9, 2014
  • Stayed: Jun 2014

Great Place to stay

5 of 5
This is my second stay with Dexter and Tiffany. They are fantastic hosts. The place is wonderful and always clean. I will be staying again. I highly recommend this house for a comfortable and clean place to stay!! I also love that they have wireless and the TV has access to Netflix.
  • Submitted: Nov 23, 2014
  • Stayed: Nov 2014

Immensely satisfying experience!!

5 of 5
My husband and I have been to Chicago 5 times. Since we are gradually getting to know the city better with every visit, I suggested we rent an apartment this time, instead of staying at the Trump as we have in the past. I scoured the internet looking for a rental comparable to a 5 star hotel and when I came upon this apartment I knew it was perfect for our needs. We were my husband and myself and one of our work mates, so the 2 bedroom/2 bathroom arrangement was exactly what we were looking for. Upon arrival, we felt as though we had died and gone to luxury heaven as the apartment was exactly as it had been showcased ...only better in real life. I have always dreamed of the true Chicago experience, which is difficult to have in a hotel room, but this apartment delivered on so many levels! The apartment was very well-appointed with all the kitchenware we required for our breakfast "at home", so all we had to do was take the elevator downstairs and literally under the apartment was Mariano’s Fresh Market, where we picked up all our groceries, including fresh baked bread and croissants. One of my favorite memories of our stay was the night we went to Whole Foods Market (just a couple blocks up) and brought our smorgasbord dinners home to eat on our private patio as we watched the sun set. Marvelous! The place is clean and has everything we needed while there. The property has a vast number of amenities (swimming pools indoor/outdoor, gym, game room, spa, lounge area, media room, business center...etc..etc). You will truly feel like you are staying in a five star hotel. The subway station is a short block away. The neighborhood has many restaurants to choose from and as foodies we felt like we were in heaven. If you enjoy walking, it is an easy walk (1 block) to Michigan Avenue shopping and 2 blocks to Millennium Park. You truly do not need a car, as the property is right in the middle of it all. I cannot say enough good things about Nadiya and her apartment and we cannot wait to stay again!
  • Submitted: Nov 4, 2014
  • Stayed: Oct 2014