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 - 74 of 74 | Prev 1 2 3 |
Description
Type
Beds
Baths
Sleeps
Avg. Rate
Beautiful Furnished Condo
$150 nightly, Corporate rental or Vacation Condo Beautiful furnished lake Michigan view from the 27th floor, condo 1st...
$150 nightly, Corporate rental or Vacation Condo Beautiful furnished lake Michigan view from the 27th floor, condo 1st...
Condo
2
2
4
$150/nt
$99 per Bedroom* 2BR- Awesome
Step outside and you'll find yourself in Chicago's hottest emerging neighborhood—the trendy Fulton River District embracing...
Step outside and you'll find yourself in Chicago's hottest emerging neighborhood—the trendy Fulton River District embracing...
Condo
2
2
6
$179/nt
Beautiful Furnished Condo by Lake
Beautiful brick building on Belmont Harbor, 2 Br, 2 Bth Home. 1 1/2 Blk From Lake & Transportation (CTA and EL) Large...
Beautiful brick building on Belmont Harbor, 2 Br, 2 Bth Home. 1 1/2 Blk From Lake & Transportation (CTA and EL) Large...
Condo
2
2
4
$3,600/mth
Downtown Mansion - Rent one room or
The Hansen House Mansion was designed in 1886 by a prominent architect, Harald M. Hansen for his own family, and it now...
The Hansen House Mansion was designed in 1886 by a prominent architect, Harald M. Hansen for his own family, and it now...
Guesthouse
4
3.5
10
$150/nt
$99 per Bedroom* 4BR- Gorgeous
This 4- bedroom modern single family home has style and sleek written all over it - from the exterior to the interior! Located...
This 4- bedroom modern single family home has style and sleek written all over it - from the exterior to the interior! Located...
Home
4
3
10
$449/nt
Corporate or Vacation Rental
Features 3 "independent" self catering units in the same building with fully functional kitchens. Coffee, tea, snacks,...
Features 3 "independent" self catering units in the same building with fully functional kitchens. Coffee, tea, snacks,...
Condo
3
1
7
$183/nt
$1,200/wk
$2,900/mth
$1,200/wk
$2,900/mth
$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
$2,200/wk
$4,800/mth
$4,800/mth
$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
$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
$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
$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
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
$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
$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
$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*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* 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
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
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
Chicago Skyline View Condo
Spacious 2br 2ba condo west of the loop on the 8th floor of a nine story new condo building.Great for short or long term vacati...
Spacious 2br 2ba condo west of the loop on the 8th floor of a nine story new condo building.Great for short or long term vacati...
Condo
2
2
4
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
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
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