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Chicago Long Term Vacation Rentals with Online Payment(92)

92 Results
$260 - $450
per night
3 - 5 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night min stay
(199)
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 4 night min stay
(60)
  • 2 BR,
  • 1 BA,
  • Sleeps 7
2 - 3 night min stay
(134)
$625 - $1,235
per night
3 - 5 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 5 night min stay
(13)
$195 - $250
per night
2 - 4 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 - 4 night min stay
(8)
$625 - $1,253
per night
3 - 5 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 5 night min stay
(116)
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
3 - 4 night min stay
(32)
$550 - $1,110
per night
3 - 5 night min stay
  • 2 BR,
  • 3 BA,
  • Sleeps 8
3 - 5 night min stay
(51)
$550 - $1,110
per night
3 - 5 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 7
3 - 5 night min stay
(35)
$169 - $199
per night
2 - 4 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 4 night min stay
(23)
$625 - $1,235
per night
3 - 5 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 5 night min stay
(53)
$199 - $269
per night
2 - 5 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 5 night min stay
(30)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 night min stay
(38)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 4 night min stay
(20)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 5 night min stay
(12)
$115 - $215
per night
3 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 10
3 night min stay
(14)
$799 - $899
per night
2 - 4 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 4 night min stay
(4)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
4 - 5 night min stay
(14)
  • 3 BR,
  • 1 BA,
  • Sleeps 8
3 - 4 night min stay
1 Review
$165 - $255
per night
3 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 night min stay
(4)
$439
per night
3 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night min stay
(65)
$189 - $325
per night
3 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 night min stay
1 Review
$90 - $149
per night
3 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
3 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
27 - 30 night min stay
1 Review
  • 4 BR,
  • 2 BA,
  • Sleeps 9
(25)
  • 4 BR,
  • 2 BA,
  • Sleeps 9
(31)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
(33)
  • 4 BR,
  • 2 BA,
  • Sleeps 10
3 night min stay
1 Review
$1,225
per week
7 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 3
7 night min stay
$395 - $465
per night
2 - 4 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 10
2 - 4 night min stay
(8)
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Recent Chicago Reviews

Spectacular Chicago penthouse

5 of 5
We used this property to celebrate our parents 50th wedding anniversary. The accommodations were very comfortable, spacious and extremely well maintained. The property also had little extras (spices, cling wrap etc) which made cooking during our stay easier and more enjoyable. The information provided by our hosts and the interactions with them were excellent. The location is second to none for a downtown Chicago experience and is conveniently located by many restaurants, stores (shops and grocery) and was close to points of interest or close to public transportation options to go wherever we wanted. A car truly is not needed to take full advantage of the property. We travel to chicago annually and will consider this property for our next trip. We would Highly recommend this property to fily or friends.
  • Submitted: Mar 28, 2015
  • Stayed: Mar 2015

Perfect location, clean, and awesome owners !

5 of 5
Wonderful house in a nice neighborhood. Situated very close to everything you'd want to do in and around the greater Chicago area. Owner is very personable and ensured our comfort and needs were met. Very well kept home with upgrades and amenities rarely experienced :) Jacuzzi was very clean and ready, garage space provided. We have definitely found a permanent place to stay when we go back!
  • Submitted: Mar 27, 2015
  • Stayed: Mar 2015

What a truly delightful find!!

5 of 5
It is my pleasure to recommend this property to most anyone who needs "a home away from home." My husband had serious surgery at Northwestern Hospital and our daughters traveled some distance to support us. This apartment was perfect for us girls while my husband was in the hospital. After his discharge from the hospital, my husband and I were greeted with warm hugs and delicious pastries made by our generous host - Nadiya. At that point it was just the two of us in this darling unit. Nadiya treated us like family and just looking at the picture above again - makes me homesick for it. The unit and owner are both a true delight! Thanks again for making us feel so at “home” in your home. We shall return!!!
  • Submitted: Mar 17, 2015
  • Stayed: Feb 2015