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 75 | Prev 1 2 3 Next |
Description
Type
Beds
Baths
Sleeps
Avg. Rate
$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
$89 per Bedroom*3BR- Graystone
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
3
3
8
$99 per Bedroom* 4BR- Beautifully
Elegant 3 level home in central Chicago location! This home is ideal for those who wish to explore what the great city of...
Elegant 3 level home in central Chicago location! This home is ideal for those who wish to explore what the great city of...
Home
4
3.5
10
$99 Per Bedroom* 6br- Family
Whether you are looking for luxury, comfort, or just sheer quality - you will get it all from this beautifully furnished...
Whether you are looking for luxury, comfort, or just sheer quality - you will get it all from this beautifully furnished...
Home
6
5
12
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
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
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
$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
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
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
Downtown Designer Penthouse
Our 5 star condominium is located just steps from the world's best shopping, dining, culture, and entertainment. 30 East...
Our 5 star condominium is located just steps from the world's best shopping, dining, culture, and entertainment. 30 East...
Condo
2
2
6
$393/nt
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
$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
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
Spacious meets Luxury & Location
Treat your self to this brand new rental! Finally a place that can accommodate large groups, while offering modern luxury....
Treat your self to this brand new rental! Finally a place that can accommodate large groups, while offering modern luxury....
Townhouse
10
8
28
$600/nt
$4,400/wk
$8,000/mth
$4,400/wk
$8,000/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
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
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
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
$136/nt
$850/wk
$2,700/mth
$850/wk
$2,700/mth
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
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
Rent a luxurious Condo in Chicago!
Rent a luxurious condo! Gorgeous three story building with all the elegant charm. You are guaranteed that you will not regret...
Rent a luxurious condo! Gorgeous three story building with all the elegant charm. You are guaranteed that you will not regret...
Condo
3
2
8
$185/nt
$1,100/wk
$1,100/wk
$99 per Bedroom*2BR- Spectacular
Fully furnished, 2 bedroom, 2 bathroom condo in the heart of the West Loop/River West/Downtown. Close to public transportatio...
Fully furnished, 2 bedroom, 2 bathroom condo in the heart of the West Loop/River West/Downtown. Close to public transportatio...
Condo
2
2
6
$239/nt