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Chicago Vacation Rentals with Online Payment(210)

210 Results
$429 - $479
per night
3 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 9
3 night minimum stay
(25)
$199 - $229
per night
3 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 night minimum stay
(33)
  • 4 BR,
  • 2 BA,
  • Sleeps 10
3 night minimum stay
1 Review
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
(22)
$295 - $475
per night
2 - 4 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 10
2 - 4 night minimum stay
(3)
$1,400
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 night minimum stay
(5)
$299 - $399
per night
2 - 3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 3 night minimum stay
(12)
$250
per night
3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 10
3 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 2
3 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
4 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 4 night minimum stay
(5)
$199 - $249
per night
2 - 4 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 - 4 night minimum stay
(24)
  • 3 BR,
  • 1 BA,
  • Sleeps 6
2 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
$129 - $219
per night
3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
3 night minimum stay
2 Reviews
$980
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 3
7 night minimum stay
$1,800
per month
31 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
31 night minimum stay
$200
per night
2 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 8
2 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 6
3 night minimum stay
(41)
$235 - $995
per night
2 night minimum stay
  • 7 BR,
  • 5 BA,
  • Sleeps 22
2 night minimum stay
(15)
$175 - $315
per night
2 - 4 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 4 night minimum stay
(18)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
(3)
  • 2 BR,
  • 2 BA,
  • Sleeps 5
2 night minimum stay
(4)
$159 - $229
per night
2 - 4 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 - 4 night minimum stay
(21)
$2,670 - $3,420
per month
30 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
30 night minimum stay
1 Review
  • 1 BR,
  • 1 BA,
  • Sleeps 4
30 night minimum stay
(45)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
$129 - $179
per night
1 - 3 night minimum stay
  • Studio,
  • 1 BA,
  • Sleeps 4
1 - 3 night minimum stay
$250
per night
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 4
2 night minimum stay
$159
per night
2 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
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Recent Chicago Reviews

FABULOUS CONDO WITH AMAZING LAKE VIEWS!

5 of 5
Our family of four celebrated Christmas in Chicago, and all agreed that this was a perfect condo! The layout, furnishings, and stunning views from all three windows were perfect. We will request this condo again when visiting since the location is convenient for walking everywhere: to the lake, shopping, many dining options, a variety of markets, and the business loop. Margarita is very hospitable .
  • Submitted: Jan 3, 2015
  • Stayed: Dec 2014

Fantastic place, great value

5 of 5
I have actually rented this property twice, once for a personal trip and once for work. Went to Chicago with a few friends for vacation and had a great time - apartment is amazing and very comfortable. Close to downtown and all the main attractions of Chicago - really well laid out and nice features like the luxury bathroom, fireplace and big kitchen. Fast internet, lots of workspace to get other things done as well. Quiet and cozy and met all of my needs. I couldn't have been happier with my choice and will definitely stay here again when I'm back in Chicago.
  • Submitted: Dec 16, 2014
  • Stayed: Nov 2014

PERFECT LOCATION

5 of 5
We usually stay in an upscale downtown hotel while in Chicago; however, this trip was different. Our daughter was returning from a 4 month vacation abroad and we wanted a "home-like" environment, conducive to family time. I also wanted a safe place for our daughter to stay while she re-acclimated to life in the States. This apartment fit our needs perfectly. THE LOCATION: The apartment is located on a tree lined street with updated multi-million dollar homes and within close proximity to shopping, restaurants, and transportation. The location could not have been better. Street parking (permits provided) was never a problem. The area felt safe and it was quiet yet only 15 minute drive to downtown. THE APARTMENT: The description and previous reviews accurately describe the apartment. Though updated, it is still an antique complete with dark hardwoods and deeply stained built-ins. What it lacks as a consequence of its age (master bathroom, small bedrooms, small but functional shower) it compensates in warmth and coziness. Though we did not cook, the kitchen appeared to be well equipped. The apartment was clean, furniture appeared new, seating was comfortable and both furnaces kept us warm. If you are one who can appreciate the nuances of an antique, this is a great apartment. THE MANAGEMENT: We have rented through VRBO/HomeAway both in the U.S. and internationally. The management style has differed with each property. The management of this property was perfect for my personality. We had contact only when necessary. In fact, he was agreeable to some last minute changes in our dates. He was quick to call me back when needed. Most importantly, I found the management to be trustworthy. He did everything he said he would do and the apartment was everything he described. OVERALL: This apartment is a great find in a perfect location: warm and cozy, not new and modern. The management is trustworthy and exceeded my expectations. We will definitely try to stay in this same property in the future.
  • Submitted: Dec 12, 2014
  • Stayed: Dec 2014