Chicago Vacation Rentals in Illinois
Our Chicago vacation rentals section includes the apartment, home, guesthouse, townhouse and condo rentals listed below.
Please click on the description to view more information about any of the vacation rentals in Chicago, Illinois.
Our inventory of Chicago condo rentals changes frequently, so please bookmark this page and check back often. You may also be interested in Beverly Shores (37 miles), Michigan City (41 miles), New Buffalo (47 miles), Union Pier (50 miles), and Sawyer (55 miles) for additional vacation rental options.
| Results 51 - 75 of 75 | Prev 1 2 3 |
Description
Type
Beds
Baths
Sleeps
Avg. Rate
Chicago Vaction Rental - Great
Tasteful and fully furnished three bedroom condo in desired Edgewater neighborhood. Bright, with understated elegance. This...
Tasteful and fully furnished three bedroom condo in desired Edgewater neighborhood. Bright, with understated elegance. This...
Condo
3
1
6
$175/nt
$1,102/wk
$4,200/mth
$1,102/wk
$4,200/mth
The Convenience Of Home Away From
This Beautiful, Spacious Third Floor Walk- Up, 3 Bedroom, 1 Bathroom Accomodation Is Conveniently Located Walking Distance...
This Beautiful, Spacious Third Floor Walk- Up, 3 Bedroom, 1 Bathroom Accomodation Is Conveniently Located Walking Distance...
Apartment
3
1
6
$300/nt
$1,400/wk
$1,400/wk
A Warm Welcome to my home - Bienvenu
Two bedroom one bath completely re- built in 2006. All new furniture and bright atmosphere conveniently located on the first...
Two bedroom one bath completely re- built in 2006. All new furniture and bright atmosphere conveniently located on the first...
Condo
2
1
4
$2,800/mth
Large Executive Studio( Wrigley
The property in our garden apartment has been fully remodeled and was recently converted into two units separated by a door...
The property in our garden apartment has been fully remodeled and was recently converted into two units separated by a door...
Apartment
1
1
6
$136/nt
$850/wk
$2,700/mth
$850/wk
$2,700/mth
Beautiful Getaway Vacation Condo
Stylish and affordable at the same time. This is what you will find in this beautifully furnished 2 bedroom/2bath vacation...
Stylish and affordable at the same time. This is what you will find in this beautifully furnished 2 bedroom/2bath vacation...
Condo
2
2
4
$130/nt
$129 per Bedroom* 4BR- Downtown Home
Fantastic contemporary home with a 2+ attached garage & fenced yard in a fantastic location. Smart wiring throughout. Gourme...
Fantastic contemporary home with a 2+ attached garage & fenced yard in a fantastic location. Smart wiring throughout. Gourme...
Home
4
3
10
$129 Per Bedroom* 2br - New Wrigley
This brand new 2- bedroom will blow you away. The 1400 sq. foot interior is decked with contemporary and traditional finishes....
This brand new 2- bedroom will blow you away. The 1400 sq. foot interior is decked with contemporary and traditional finishes....
Condo
2
2
8
$129 per Bedroom*2BR Amazing View of
2BR Condo in Downtown Chicago, walking distance to Navy Pier, Millenium Park, Magnificent Mile, Lake. Beautiful Views...
2BR Condo in Downtown Chicago, walking distance to Navy Pier, Millenium Park, Magnificent Mile, Lake. Beautiful Views...
Condo
2
2
6
$129 Per Bedroom* 2br- Walk Mag
Featuring a modern contemporary feel, the Chicago apartments offers dramatic finishes including tiled entries, granite island...
Featuring a modern contemporary feel, the Chicago apartments offers dramatic finishes including tiled entries, granite island...
Condo
2
2
6
$99 per Bedroom* 6BR- Homein Beautifu
This new 6- bedroom will blow you away. The interior is decked with contemporary and traditional finishes. The location is...
This new 6- bedroom will blow you away. The interior is decked with contemporary and traditional finishes. The location is...
Condo
6
4.5
14
$99 per Bedroom* 4BR- Luxurious
See Chicago like a star! Oversized 4 bedroom home. Total of 6 new beds in this home. This home has it all... hardwood floors,...
See Chicago like a star! Oversized 4 bedroom home. Total of 6 new beds in this home. This home has it all... hardwood floors,...
Home
4
3.5
12
$89 per Bedroom* 15BR- New Wrigleyvi
This brand new 15- bedroom will blow you away. The 1600 sq. foot, per unit, interior is decked with contemporary and tradition...
This brand new 15- bedroom will blow you away. The 1600 sq. foot, per unit, interior is decked with contemporary and tradition...
Condo
15
15
40
$139 Per Bedroom* 4br- Multi- Level
Gorgeous design single family on a double wide lot provides the perfect urban home! Exquisite attention to detail is evident...
Gorgeous design single family on a double wide lot provides the perfect urban home! Exquisite attention to detail is evident...
Home
4
4
10
$129 Per Bedroom* 4br - Beautiful
Brazilian cherry wood floors throughout this beautiful home. Gourmet kitchen with Silestone; stainless steel appliances includ...
Brazilian cherry wood floors throughout this beautiful home. Gourmet kitchen with Silestone; stainless steel appliances includ...
Home
4
5.5
12
Furnished apartments or individual
Choose from complete apartments in an 1891 home or individual guestrooms in an 1886 mansion, both in the heart of downtown...
Choose from complete apartments in an 1891 home or individual guestrooms in an 1886 mansion, both in the heart of downtown...
Apartment
6
3
12
$89 per Bedroom* 6BR- Breathtaking
This is an amazing graystone home in historic Wrigley neighborhood. The house has been completely revamped to meet all the...
This is an amazing graystone home in historic Wrigley neighborhood. The house has been completely revamped to meet all the...
Condo
2
2
6
Magnificent Mile 1 BR - near
This magnificent one bedroom, one bathroom is located less than two blocks from Chicago's famed Magnificent Mile on the Gold...
This magnificent one bedroom, one bathroom is located less than two blocks from Chicago's famed Magnificent Mile on the Gold...
Condo
1
1
4
$185/nt
$1,150/wk
$2,100/mth
$1,150/wk
$2,100/mth
The Wayne Manor
Gather your group and get ready to live in comfort! Lots of open space, good size bedrooms and bathrooms. This Beautiful...
Gather your group and get ready to live in comfort! Lots of open space, good size bedrooms and bathrooms. This Beautiful...
Home
4
4
10
Call4specials!! Gold Coast Short/
Our condo is centrally located in the heart of Gold Coast, only 2 blocks from the Magnificent Mile. Our two bedroom condo...
Our condo is centrally located in the heart of Gold Coast, only 2 blocks from the Magnificent Mile. Our two bedroom condo...
Condo
2
1
4
ZEN Euro Modern Luxury - Dining/Mart
W Hubbard, Chicago, Il 60610 Come And Experience Life In River North. With The Newest Nightclubs, Restuarants,...
W Hubbard, Chicago, Il 60610 Come And Experience Life In River North. With The Newest Nightclubs, Restuarants,...
Condo
1
1
6
$175/nt
Wicker Park Corporate / Vacation
- Huge 2200 sq- feet condo in the middle of fun Wicker Park neighborhood - Ideal for a family or friends on vacation/work...
- Huge 2200 sq- feet condo in the middle of fun Wicker Park neighborhood - Ideal for a family or friends on vacation/work...
Condo
3
2
7
2 Bedroom, 1 Bath - Sep 10
- 2 bedroom, 1 bath, 1 day bed in Living room - Approx 1000 sq feet Unit located in central Wicker Park - Chicago -...
- 2 bedroom, 1 bath, 1 day bed in Living room - Approx 1000 sq feet Unit located in central Wicker Park - Chicago -...
Condo
2
1
5
$166/nt
$1,000/wk
$2,300/mth
$1,000/wk
$2,300/mth
Downtown Penthouse!!! Great Location!!
Braz ch flrs, firepl, exposed brick, granite & stainless st, surround sound, private deck. Unit has roof rights also....
Braz ch flrs, firepl, exposed brick, granite & stainless st, surround sound, private deck. Unit has roof rights also....
Condo
2
1
4
$1,500/mth
Close To Everything/downtown
Close To Everyhing- Centrally Located In City- Walking Distance To Michigan Ave, Navy Pier, Downtown Loop. Fully Furnis...
Close To Everyhing- Centrally Located In City- Walking Distance To Michigan Ave, Navy Pier, Downtown Loop. Fully Furnis...
Condo
1
1
2
$145/nt
$1,000/wk
$2,250/mth
$1,000/wk
$2,250/mth
4500 sf. Penthouse apartment with
4500 sf. contemporary Penthouse with 1500 sf. rooftop deck with panoramic, unobstructed views of downtown Chicago skyline...
4500 sf. contemporary Penthouse with 1500 sf. rooftop deck with panoramic, unobstructed views of downtown Chicago skyline...
Apartment
4
2
10
