Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Booking Options

Location Type

Even More Filters

Features

Managed By

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

Chicago Vacation Rentals with Online Payment(207)

207 Results
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 5 night minimum stay
(19)
$335 - $460
per night
2 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
(9)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 night minimum stay
(12)
$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 6
3 - 7 night minimum stay
2 Reviews
  • 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)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
6 night minimum stay
(12)
$225 - $464
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
2 Reviews
$135 - $255
per night
3 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 - 5 night minimum stay
(4)
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 14
2 night minimum stay
2 Reviews
$439
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(63)
$155
per night
3 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 night minimum stay
1 Review
$159 - $279
per night
3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
1 Review
$250 - $400
per night
2 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 night minimum stay
1 Review
$65 - $149
per night
3 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
3 night minimum stay
$65 - $139
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
$139 - $249
per night
3 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 night minimum stay
(6)
  • 2 BR,
  • 1 BA,
  • Sleeps 8
3 night minimum stay
  • 3 BR,
  • 1 HF BA,
  • Sleeps 8
3 - 4 night minimum stay
(4)
  • 1 BR,
  • 1 BA,
  • Sleeps 3
3 night minimum stay
1 Review
$300
per night
4 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 8
4 night minimum stay
1 Review
$300 - $400
per night
1 - 2 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 12
1 - 2 night minimum stay
(30)
  • 4 BR,
  • 2 BA,
  • Sleeps 10
3 night minimum stay
(12)
$475 - $1,000
per night
2 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 5 night minimum stay
$4,980
per month
30 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 10
30 night minimum stay
(10)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 night minimum stay
2 Reviews
  • 2 BR,
  • 2 BA,
  • Sleeps 4
27 - 30 night minimum stay
Advertisement
 

Recent Chicago Reviews

Great location. Clean. Awesome amenities!

5 of 5
My husband and I stayed at Sarah's place this past weekend. Communication was great and the property was clean and well stocked with everything we needed. I am coming back to Chicago next month for a conference and plan on staying at Sarah's place again.
  • Submitted: Dec 13, 2014
  • Stayed: Dec 2014

PERFECT!

5 of 5
We stayed here for 5 nights. It could not have been a better place. The views were stunning! You can see the Lake from the living rooms windows. The beds were very comfortable. The building was in a perfect location. Walk to the Magnificent Mile- Just a block over. The Chicago river you can see peaking out between buidlings from the balacony and Short walk to all the river cruises locations (10 minutes). The red line is right across the street from the building so public transpoert is super easy. The grocery store downstairs made it easy to eat some meals in while we took in the view. Simply a brilliant stay. I will stay here any time I find myself back in Chicago!
  • Submitted: Dec 3, 2014
  • Stayed: Oct 2014

We always stay here!

5 of 5
When visiting downtown Chicago, two couples, including us, stay at Grand Plaza through Chicago Premier Suites. Parking in a covered is included with this beautiful condo located in the heart of North River. The el stop, if needed, is right out the front door. We are able to walk to Magnificent mile and many places of interest as well as restaurants. The furnishings and amenities are impeccable. It is a perfect getaway in the city and is more affordable a than paying for two hotel rooms. The view is unbelievable.
  • Submitted: Nov 13, 2014
  • Stayed: Nov 2014