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 26 - 50 of 74 | Prev 1 2 3 Next |
Description
Type
Beds
Baths
Sleeps
Avg. Rate
$89 Per Bedroom* 6br- New Duplex
This brand new 6- bedroom will blow you away. The 1600 sq. foot interior is decked with contemporary and traditional finishes....
This brand new 6- bedroom will blow you away. The 1600 sq. foot interior is decked with contemporary and traditional finishes....
Condo
6
6
16
$129 per Bedroom* 2BR Spectacular
Beautifully designed and furnished 2 bedroom 2 bath located in Michigan Avenue. This high rise condominium is next to several...
Beautifully designed and furnished 2 bedroom 2 bath located in Michigan Avenue. This high rise condominium is next to several...
Condo
2
2
6
$129 per Bedroom* 2BR- Fantastic
Featuring a modern contemporary feel, the Chicago apartments offers dramatic finishes including tiled entries, granite...
Featuring a modern contemporary feel, the Chicago apartments offers dramatic finishes including tiled entries, granite...
Condo
2
2
6
This penthouse puts you in the heart
These units have recently been renovated and includes hard wood floors, Granite countertops, Stainless steel appliances...
These units have recently been renovated and includes hard wood floors, Granite countertops, Stainless steel appliances...
Condo
2
2
6
$99 per Bedroom*7BR Luxurious Mansion
Timeless elegance with all the luxuries you can imagine, oversize lot in Blaine school district, 7 bedrooms, 5 en- suite...
Timeless elegance with all the luxuries you can imagine, oversize lot in Blaine school district, 7 bedrooms, 5 en- suite...
Condo
7
5
18
Rent a Mansion in Chicago!
Rent a Mansion in Wrigleyville! Gorgeous four story home with all the elegant charm imaginable. You are guaranteed to not...
Rent a Mansion in Wrigleyville! Gorgeous four story home with all the elegant charm imaginable. You are guaranteed to not...
Home
5
5
12
$637/nt
$3,705/wk
$11,157/mth
$3,705/wk
$11,157/mth
Hip & Happening Ontario Spot
This condo has it all. Nice balcony with gas barbeque, hardwood floors, designer bathroom with jacuzzi, large flat screen...
This condo has it all. Nice balcony with gas barbeque, hardwood floors, designer bathroom with jacuzzi, large flat screen...
Condo
1
1
4
$214/nt
$1,250/wk
$2,500/mth
$1,250/wk
$2,500/mth
$99 per Bedroom*4BR Home McCormick
This property is within minutes to downtown Chicago and lies next to all major highway intersections. It is situated next...
This property is within minutes to downtown Chicago and lies next to all major highway intersections. It is situated next...
Home
4
3.5
10
$399/nt
$1,700/wk
$3,800/mth
$1,700/wk
$3,800/mth
Beautiful Condo steps to Gold Coast
Welcome. Chicago Franklin Flat offers this 3 bedroom beautiful vacation rental. You will feel right at home here! In...
Welcome. Chicago Franklin Flat offers this 3 bedroom beautiful vacation rental. You will feel right at home here! In...
Condo
3
1
6
$207/nt
$1,375/wk
$3,800/mth
$1,375/wk
$3,800/mth
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
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
City style fully furnished condo in
Newly built fully furnished loft style condo located just one block north of McCromick Place Convention Center in Downtown...
Newly built fully furnished loft style condo located just one block north of McCromick Place Convention Center in Downtown...
Condo
1
1
3
$155/nt
$975/wk
$2,600/mth
$975/wk
$2,600/mth
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 Biddle House - A Charming
There are two fully furnished apartments available at the Biddle House. Each has two bedrooms, one bathroom, a fully equipped...
There are two fully furnished apartments available at the Biddle House. Each has two bedrooms, one bathroom, a fully equipped...
Guesthouse
4
2
11
$189/nt
$2,800/mth
$2,800/mth
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
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
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
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
$109/nt
$700/wk
$2,000/mth
$700/wk
$2,000/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
2br/2ba Furnished Downtown Condo
42th floor, overlooking city, Lake Michigan and the Chicago River. Fully furnished 2 bedroom/2 bath. Building amenities...
42th floor, overlooking city, Lake Michigan and the Chicago River. Fully furnished 2 bedroom/2 bath. Building amenities...
Condo
2
2
4
$1,325/wk
$3,475/mth
$3,475/mth
Teri's Chicago Guest Houses * Wrigleyv
Chicago Guest House on Lakewood Avenue 1 Stately Graystone with 3 Separate Apartments 1st Fl Wrigley Suite 4bdrm/ 2bth...
Chicago Guest House on Lakewood Avenue 1 Stately Graystone with 3 Separate Apartments 1st Fl Wrigley Suite 4bdrm/ 2bth...
Guesthouse
4
2
8
$495/nt
$3,118/wk
$3,118/wk
Beautiful Classic Brownstone Home-
Enjoy this newly completed high- end renovation of a classic Brownstone home with 5 spacious bedrooms, 3 full baths and home...
Enjoy this newly completed high- end renovation of a classic Brownstone home with 5 spacious bedrooms, 3 full baths and home...
Home
5
3
11
$499/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
Huge 4 Floor 2000 sq ft Chicago
Chicago's Bed & Breakfast and Hotel Alternative: This large 2000 sq ft property features amazing Chicago skyline views...
Chicago's Bed & Breakfast and Hotel Alternative: This large 2000 sq ft property features amazing Chicago skyline views...
Townhouse
3
2.5
7
$263/nt
$1,500/wk
$5,500/mth
$1,500/wk
$5,500/mth
Beautiful Executive APT.
Thank you for your interest in our vacation condo in Chicago. Our apt is very close to Wrigley field, Very well maintained....
Thank you for your interest in our vacation condo in Chicago. Our apt is very close to Wrigley field, Very well maintained....
Apartment
1
1
6
$109/nt
$700/wk
$2,000/mth
$700/wk
$2,000/mth