210 Results
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

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

Chicago Vacation Rentals with Online Payment(210)

210 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
(196)
$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
(52)
  • 3 BR,
  • 1 BA,
  • 2 HF BA,
  • Sleeps 6
2 - 4 night minimum stay
(56)
$625 - $1,235
per night
3 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 5 night minimum stay
(11)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(60)
$195 - $250
per night
2 - 4 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 - 4 night minimum stay
(7)
  • 2 BR,
  • 1 BA,
  • 2 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)
$550 - $1,110
per night
3 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 7
3 - 5 night minimum stay
(34)
$260 - $450
per night
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night minimum stay
(10)
$185 - $269
per night
2 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 5 night minimum stay
(29)
$149 - $199
per night
2 - 4 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 4 night minimum stay
(23)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 24
2 - 4 night minimum stay
(37)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(64)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(36)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(58)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(25)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night minimum stay
(19)
$204 - $925
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(8)
$165 - $300
per night
2 - 4 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 6
2 - 4 night minimum stay
(5)
$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 6
2 - 5 night minimum stay
(12)
$225 - $925
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(4)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
(64)
$115 - $215
per night
3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 10
3 night minimum stay
(10)
  • 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)
Advertisement
 

Recent Chicago Reviews

Perfect for McCormick Show

5 of 5
This property was perfect for our team working a show at McCormick Center. It was clean, well equipped, and ready when we arrived. The hot tub certainly was nice after being on our feet all day. The bonus for us was the neighborhood restaurants. I had no idea that Bridgeport would deliver such convenience and choices to fill up after working all day. Great place and location. We are booking next year now.
  • Submitted: Jan 26, 2015
  • Stayed: Jan 2015

Couldn't have asked for a better place to stay

5 of 5
We visited here for Fall Break with our 11 and 14 year old. This location was within walking distance to Michigan, easy for shopping, dining, etc. The condo was incredible with very nice top of the line finishes, great gathering room on site, courteous staff and everything. We were able to watch the Chicago Marathon runners from our window. I'd definitely stay here again. While kids were with us and it was absolutely fine, I think this is also very appropriate for a fun adult getaway as well.
  • Submitted: Jan 26, 2015
  • Stayed: Oct 2014

Excellent in all respects

5 of 5
Choosing accommodation on the Internet is always fraught with uncertainties, especially from a distance. But everything about this place exceeded expectations; great location, splendid views, clean and comfortable, convenient walking distance to much of what we wanted and access to the "El" and buses, full grocery store in the building and an inexhaustible range of restaurants all round. The apartment was spacious and well supplied with all necessities. The building itself had many more facilities indoor and outdoor than we were capable of using in the time we had available, and the doorman was a gem. Arrangements with Chicago Premier Suites for access worked impeccably (even though we were delayed until 2.00am). It all made for a memorable and very enjoyable stay in Chicago.
  • Submitted: Jan 25, 2015
  • Stayed: Sep 2014