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Save time when booking: choose rentals that accept online reservations or online payments

Chicago Vacation Rentals with Online Payment, Fireplace(64)

64 Results
$625 - $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)
$625 - $1,235
per night
3 - 5 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 5 night minimum stay
(50)
  • 3 BR,
  • 1 BA,
  • 2 HF BA,
  • Sleeps 6
2 - 4 night minimum stay
(57)
$625 - $1,235
per night
3 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 5 night minimum stay
(10)
$550 - $1,110
per night
3 - 5 night minimum stay
  • 2 BR,
  • 3 BA,
  • Sleeps 8
3 - 5 night minimum stay
(50)
$550 - $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)
$260 - $450
per night
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night minimum stay
(9)
$199 - $269
per night
2 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 5 night minimum stay
(28)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 24
2 - 4 night minimum stay
(34)
  • 4 BR,
  • 2 BA,
  • Sleeps 9
3 night minimum stay
(25)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night minimum stay
(14)
$775 - $825
per night
3 - 4 night minimum stay
  • 5 BR,
  • 5 BA,
  • Sleeps 14
3 - 4 night minimum stay
(5)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
(63)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 night minimum stay
(33)
  • 4 BR,
  • 2 BA,
  • Sleeps 9
3 night minimum stay
(30)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 3 night minimum stay
(78)
$750 - $1,375
per night
2 - 3 night minimum stay
  • 6 BR,
  • 5 BA,
  • Sleeps 11
2 - 3 night minimum stay
(20)
$799 - $899
per night
2 - 4 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 4 night minimum stay
(4)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
27 - 30 night minimum stay
$179 - $250
per night
2 - 3 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 - 3 night minimum stay
(21)
$295 - $450
per night
3 - 4 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 10
3 - 4 night minimum stay
1 Review
$1,225 - $1,400
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 night minimum stay
(5)
  • 1 BR,
  • 2 BA,
  • Sleeps 2
3 night minimum stay
$499 - $999
per night
  • 3 BR,
  • 3 BA,
  • Sleeps 10
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 4 night minimum stay
(5)
$250
per night
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 4
2 night minimum stay
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Recent Chicago Reviews

Perfection!!!

5 of 5
Our stay in this condo was pure perfection!!! It's a beautiful condo, well-maintained, very clean, well-stocked, and a perfect location. The owners were easy to work with and quick to respond. It was a perfect location for us to celebrate a 65th birthday & Christmas in the same weekend. We can't say enough about how much we loved our stay!!!
  • Submitted: Dec 23, 2014
  • 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

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