75 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Booking Options

Location Type

Even More Filters

Features

Managed By

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

Chicago Downtown Vacation Rentals with Online Payment(75)

75 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)
$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,
  • 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
2 - 4 night minimum stay
(19)
  • 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)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 night minimum stay
(24)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
(64)
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 14
2 night minimum stay
(5)
$799 - $899
per night
2 - 4 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 4 night minimum stay
(4)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
4 - 5 night minimum stay
(13)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night minimum stay
(28)
$169 - $199
per night
2 - 4 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 4 night minimum stay
(23)
$439
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(65)
  • 1 BR,
  • 1 BA,
  • Sleeps 3
3 night minimum stay
1 Review
$99 - $155
per night
3 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 night minimum stay
1 Review
  • 3 BR,
  • 3 BA,
  • Sleeps 12
2 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 10
3 night minimum stay
1 Review
$299 - $359
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(12)
$1,400
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 night minimum stay
(5)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 4 night minimum stay
(5)
  • 3 BR,
  • 1 BA,
  • Sleeps 6
2 night minimum stay
1 Review
$230 - $245
per night
2 - 3 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 - 3 night minimum stay
$399 - $799
per night
1 - 3 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 10
1 - 3 night minimum stay
$250 - $305
per night
2 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
2 night minimum stay
Advertisement
 

Recent Chicago Reviews

What a truly delightful find!!

5 of 5
It is my pleasure to recommend this property to most anyone who needs "a home away from home." My husband had serious surgery at Northwestern Hospital and our daughters traveled some distance to support us. This apartment was perfect for us girls while my husband was in the hospital. After his discharge from the hospital, my husband and I were greeted with warm hugs and delicious pastries made by our generous host - Nadiya. At that point it was just the two of us in this darling unit. Nadiya treated us like family and just looking at the picture above again - makes me homesick for it. The unit and owner are both a true delight! Thanks again for making us feel so at “home” in your home. We shall return!!!
  • Submitted: Mar 17, 2015
  • Stayed: Feb 2015

Beautiful apartment, but a bit noisy

4 of 5
The apartment itself was beautiful and the location in regards to moving around the city was great! Once we arrived in the city, we had direct contact with the owner, who was very accommodating with anything we needed. Our only "complaint" was that the apartment is located two floors above a very popular and busy bar. Anytime the bar was playing music, we could feel and hear the bass consistently. At the front of the apartment, you could also hear the crowd noise from the street. However, given that we were in Chicago for the nightlife, we didn't find it too troublesome. Overall, we really enjoyed our stay and the owner was a pleasure to work with.
  • Submitted: Mar 17, 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