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Vacation Rentals
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USA
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Illinois
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Chicago
4
BR /
4
BA /
Sleeps
11
From $600/nt
Featured
3
BR /
Sleeps
30
Featured
4
BR /
4
BA /
Sleeps
14
From $20,150/month
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Sleeps
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From $265/nt
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Sleeps
7
From $425/nt
Featured
Chicago Wheelchair Accessible
(44)
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Accepts Online Payments
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Bedrooms: Most to Least
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Special Offers First
6 Bed/6 Bath Huge Contemporary House in the Suburbs of Chicago
6 Bedrooms,
4
Bathrooms
,
2
Half Baths
, Sleeps 30
$650 - $950
per night
6 Bed/6 Bath Huge Contemporary House in the Suburbs of Chicago
Book it Now!
2 - 3 night minimum stay
6
BR,
4
BA,
2
HF BA,
Sleeps
30
Illinois
>
Chicago House
#3021174
(46)
Compare
Condo in Hot Bucktown / Wicker Park Neighborhood
2 Bedrooms,
2
Bathrooms
, Sleeps 6
Condo in Hot Bucktown / Wicker Park Neighborhood
2
BR,
2
BA,
Sleeps
6
Illinois
>
Chicago Condo
#374687
(28)
Compare
Summer Specials on Luxurious Living! Email Now for Unbeatable Values!
2 Bedrooms,
2
Bathrooms
, Sleeps 6
Summer Specials on Luxurious Living! Email Now for Unbeatable Values!
2
BR,
2
BA,
Sleeps
6
Illinois
>
Chicago Condo
#923719
(9)
Compare
Beautiful River North Chicago Condo
1 Bedrooms,
1
Bathroom
, Sleeps 3
$127 - $180
per night
Beautiful River North Chicago Condo
4 night minimum stay
1
BR,
1
BA,
Sleeps
3
Illinois
>
Chicago Condo
#3485336
Compare
Lovely Streeterville Apartment
1 Bedrooms,
1
Bathroom
, Sleeps 3
$127 - $140
per night
Lovely Streeterville Apartment
4 night minimum stay
1
BR,
1
BA,
Sleeps
3
Illinois
>
Chicago Apartment
#3500726
Compare
2bd unit on Michigan ave
2 Bedrooms,
1
Bathroom
,
1
Half Bath
, Sleeps 4
$149 - $329
per night
2bd unit on Michigan ave
3 night minimum stay
2
BR,
1
BA,
1
HF BA,
Sleeps
4
Illinois
>
Chicago Apartment
#391036
1 Review
Compare
5 minutes ride to downtown Bathhouse 2bd
1 Bedrooms,
1
Bathroom
, Sleeps 4
$149 - $169
per night
5 minutes ride to downtown Bathhouse 2bd
3 night minimum stay
1
BR,
1
BA,
Sleeps
4
Illinois
>
Chicago Apartment
#391031
Compare
Cheap studio downtown in great location
1 Bedrooms,
1
Bathroom
, Sleeps 3
Cheap studio downtown in great location
1
BR,
1
BA,
Sleeps
3
Illinois
>
Chicago Apartment
#391037
Compare
$129/night after Oct 15th !!! Close to Lincoln Prk. Free St Parking!
2 Bedrooms,
2
Bathrooms
, Sleeps 4
$129/night after Oct 15th !!! Close to Lincoln Prk. Free St Parking!
2
BR,
2
BA,
Sleeps
4
Illinois
>
Chicago Apartment
#391032
1 Review
Compare
Beautiful and Luxurious 3 Bedroom / 2 Bathroom Condo
3 Bedrooms,
2
Bathrooms
, Sleeps 8
$250 - $360
per night
Beautiful and Luxurious 3 Bedroom / 2 Bathroom Condo
3 - 4 night minimum stay
3
BR,
2
BA,
Sleeps
8
Illinois
>
Chicago Condo
#247326
(42)
Compare
Beautiful 2 Bedroom, 2 Bath Condo in Andersonville with a patio
2 Bedrooms,
2
Bathrooms
, Sleeps 6
$200 - $280
per night
Beautiful 2 Bedroom, 2 Bath Condo in Andersonville with a patio
3 - 4 night minimum stay
2
BR,
2
BA,
Sleeps
6
Illinois
>
Chicago Condo
#990184
Compare
Beautiful and Luxurious Andersonville 2 BR /2 BA
2 Bedrooms,
2
Bathrooms
, Sleeps 6
$220 - $300
per night
Beautiful and Luxurious Andersonville 2 BR /2 BA
3 - 4 night minimum stay
2
BR,
2
BA,
Sleeps
6
Illinois
>
Chicago Condo
#974965
Compare
Fantastic Downtown Chicago Condo
1 Bedrooms,
1
Bathroom
, Sleeps 3
$127 - $150
per night
Fantastic Downtown Chicago Condo
4 night minimum stay
1
BR,
1
BA,
Sleeps
3
Illinois
>
Chicago Condo
#3472100
Compare
Fantastic Downtown Chicago Condo
2 Bedrooms,
2
Bathrooms
, Sleeps 5
$167 - $200
per night
Fantastic Downtown Chicago Condo
4 night minimum stay
2
BR,
2
BA,
Sleeps
5
Illinois
>
Chicago Condo
#3486085
Compare
Beautiful modern loft close to Chicago attractions and McCormick Place
1 Bedrooms,
1
Bathroom
, Sleeps 4
$160 - $180
per night
Beautiful modern loft close to Chicago attractions and McCormick Place
3 night minimum stay
1
BR,
1
BA,
Sleeps
4
Illinois
>
Chicago Condo
#902863
(45)
Compare
Amazing Views of the Chicago Skyline from this Luxury Condo
2 Bedrooms,
2
Bathrooms
, Sleeps 4
$110 - $140
per night
Amazing Views of the Chicago Skyline from this Luxury Condo
2 night minimum stay
2
BR,
2
BA,
Sleeps
4
Illinois
>
Chicago Condo
#222038
(36)
Compare
The Penthouse #1
3 Bedrooms,
2
Bathrooms
, Sleeps 8
$590 - $760
per night
The Penthouse #1
3
BR,
2
BA,
Sleeps
8
Illinois
>
Chicago Condo
#237915
(89)
Compare
Enjoy Fab Lake and Skyline Views + Luxury Comfort at Prime Downtown Location!!
2 Bedrooms,
2
Bathrooms
, Sleeps 6
$300
per night
Enjoy Fab Lake and Skyline Views + Luxury Comfort at Prime Downtown Location!!
2 night minimum stay
2
BR,
2
BA,
Sleeps
6
Illinois
>
Chicago Condo
#177863
(25)
Compare
Lakeshore, Millennium Park High Rise
2 Bedrooms,
2
Bathrooms
, Sleeps 6
Lakeshore, Millennium Park High Rise
2
BR,
2
BA,
Sleeps
6
Illinois
>
Chicago Condo
#204526
(59)
Compare
Luxurious, Urban, Modern 1BR High-Rise Condominium in Downtown Chicago for you!!
1 Bedrooms,
1
Bathroom
, Sleeps 2
$200 - $250
per night
Luxurious, Urban, Modern 1BR High-Rise Condominium in Downtown Chicago for you!!
2 night minimum stay
1
BR,
1
BA,
Sleeps
2
Illinois
>
Chicago Condo
#299812
(8)
Compare
Amenities Galore-Amazing Skyline, Lake, River Views, Walk Everywhere
2 Bedrooms,
2
Bathrooms
, Sleeps 6
Amenities Galore-Amazing Skyline, Lake, River Views, Walk Everywhere
2
BR,
2
BA,
Sleeps
6
Illinois
>
Chicago Apartment
#983900
(10)
Compare
Brand New Construction Guesthouse, Fully-Furnished, Upscale, Elegant, Modern,
1 Bedrooms,
1
Bathroom
, Sleeps 4
Brand New Construction Guesthouse, Fully-Furnished, Upscale, Elegant, Modern,
1
BR,
1
BA,
Sleeps
4
Illinois
>
Chicago Apartment
#299450
(17)
Compare
Urban Heaven! Affordable Luxury.. Walk Everywhere! Views!
3 Bedrooms,
2
Bathrooms
, Sleeps 6
Urban Heaven! Affordable Luxury.. Walk Everywhere! Views!
3
BR,
2
BA,
Sleeps
6
Illinois
>
Chicago Apartment
#966826
(4)
Compare
Downtown Luxury Condo
1 Bedrooms,
1
Bathroom
, Sleeps 3
$3,400
per month
Downtown Luxury Condo
28 night minimum stay
1
BR,
1
BA,
Sleeps
3
Illinois
>
Chicago Condo
#200371
1 Review
Compare
Luxury Highrise Suite with Panoramic Views of Chicago's Skyline
1 Bedrooms,
1
Bathroom
, Sleeps 2
$185 - $225
per night
Luxury Highrise Suite with Panoramic Views of Chicago's Skyline
3 night minimum stay
1
BR,
1
BA,
Sleeps
2
Illinois
>
Chicago Condo
#378791
2 Reviews
Compare
Floor to Ceiling Windows Overlooking Chicago's Skyline!
2 Bedrooms,
2
Bathrooms
, Sleeps 6
Floor to Ceiling Windows Overlooking Chicago's Skyline!
2
BR,
2
BA,
Sleeps
6
Illinois
>
Chicago Apartment
#442390vb
Compare
Save! A Guest Favorite W /Amazing Views! Luxurious Amenities!
2 Bedrooms,
2
Bathrooms
, Sleeps 6
Save! A Guest Favorite W /Amazing Views! Luxurious Amenities!
2
BR,
2
BA,
Sleeps
6
Illinois
>
Chicago Apartment
#442045vb
2 Reviews
Compare
17 More choices from HomeAway International Websites
Penthouse Duplex #2
3 Bedrooms,
3
Bathrooms
, Sleeps 8
$600 - $800
per night
Penthouse Duplex #2
Book it Now!
3 - 4 night minimum stay
3
BR,
3
BA,
Sleeps
8
Illinois
>
Chicago Condo
#109064vb
(26)
Compare
Premium Condo in Chicago's Gold Coast with Gorgeous Lake Views
1 Bedrooms,
1
Bathroom
, Sleeps 4
$145 - $395
per night
Premium Condo in Chicago's Gold Coast with Gorgeous Lake Views
Book it Now!
2 - 30 night minimum stay
1
BR,
1
BA,
Sleeps
4
Illinois
>
Chicago Condo
#445376vb
2 Reviews
Compare
Charming Executive Condo! Cubs Fun? Close to Wrigley Field.
1 Bedrooms, Sleeps 4
$130 - $160
per night
Charming Executive Condo! Cubs Fun? Close to Wrigley Field.
3 - 7 night minimum stay
1
BR,
Sleeps
4
Illinois
>
Chicago Condo
#263916vb
(12)
Compare
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