113 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Condos
Cottages
Estates
Homes
Studios
Villas
Barns
Boats
Bungalows
Cabins
Castles
Chalets
Farmhouses
Hotels
Lodges
Townhomes
Yachts

Booking Options

Location Type

Even More Filters

Features

Managed By

113 Results
Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Chicago Vacation Rentals(113)

113 Results
$625 - $1,253
per night
3 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 5 night minimum stay
(116)
$260 - $450
per night
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night minimum stay
(198)
$415 - $875
per night
3 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 5 night minimum stay
(105)
$625 - $1,235
per night
3 - 5 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 5 night minimum stay
(53)
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 4 night minimum stay
(59)
  • 2 BR,
  • 1 BA,
  • Sleeps 7
2 - 3 night minimum stay
(134)
$625 - $1,235
per night
3 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 5 night minimum stay
(12)
$195 - $250
per night
2 - 4 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 - 4 night minimum stay
(8)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(62)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(60)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(64)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(36)
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
3 - 4 night minimum stay
(32)
$550 - $1,110
per night
3 - 5 night minimum stay
  • 2 BR,
  • 3 BA,
  • Sleeps 8
3 - 5 night minimum stay
(51)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(26)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 4 night minimum stay
(19)
$260 - $450
per night
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night minimum stay
(12)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 5 night minimum stay
(12)
$550 - $1,110
per night
3 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 7
3 - 5 night minimum stay
(34)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 24
1 - 4 night minimum stay
(39)
$276 - $925
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(8)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 night minimum stay
(24)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
(64)
$199 - $269
per night
2 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 5 night minimum stay
(30)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
(38)
$775 - $825
per night
3 - 4 night minimum stay
  • 5 BR,
  • 5 BA,
  • Sleeps 14
3 - 4 night minimum stay
(5)
$276 - $925
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(4)
$276 - $925
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(3)
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 14
2 night minimum stay
(5)
$115 - $215
per night
3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 10
3 night minimum stay
(14)
Advertisement
 

Recent Chicago Reviews

Quality and Convenience

5 of 5
Enjoyed a nice long weekend with my family of 5. The property was clean and conveniently located to the Mag Mile shopping, restaurants, etc. The description provided in the listing matched what we found upon arrival and our overall experience. We would do this again!
  • Submitted: Mar 19, 2015
  • Stayed: Mar 2015

Clean & home comfort!!

5 of 5
The property was very clean and has the home comfort! Will definitely stay again!! Location is great also! Owner very easy to work with and quick to repond!
  • Submitted: Mar 16, 2015
  • Stayed: Mar 2015

Fantastic Stay in Chicago!

5 of 5
This rental is extremely spacious and the location/view were amazing! We were able to walk to many restaurants, shops, and bars, and would've walked to much more had it not been so cold. The unit is furnished beautifully and we felt right at home. Our only complaint is that the air in the condo was extremely dry, likely due to the cold winter weather. A humidifier would bring added comfort. We look forward to returning sometime sooner than later!
  • Submitted: Mar 6, 2015
  • Stayed: Feb 2015