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 1 - 25 of 75 | 1 2 3 Next |
Description
Type
Beds
Baths
Sleeps
Avg. Rate
East Rogers Park - Evanston
This is our "budget rental" for Chicago Unit rents for: $1500 per month $85 per night for less than 7 nights booking,...
This is our "budget rental" for Chicago Unit rents for: $1500 per month $85 per night for less than 7 nights booking,...
Apartment
1
1
2
$85/nt
$585/wk
$1,338/mth
$585/wk
$1,338/mth
Location! Location! Location! Navy
Location Location Location! Can't Beat It! Set In The Heart Of Downtown Chicago, Our Chicago Apt Is Ideally...
Location Location Location! Can't Beat It! Set In The Heart Of Downtown Chicago, Our Chicago Apt Is Ideally...
Condo
2
2
6
$265/nt
China Doll Guest House
In Chicago's Lincoln Park neighborhood, China Doll offers complete self- contained apartment suites with private entrances....
In Chicago's Lincoln Park neighborhood, China Doll offers complete self- contained apartment suites with private entrances....
Apartment
2
1
6
$239/nt
$1,575/wk
$1,575/wk
Sp Suites - Millennium Park
These Vacation Rentals are located in the New East Side, a mixed- use neighborhood east of Michigan Avenue that includes...
These Vacation Rentals are located in the New East Side, a mixed- use neighborhood east of Michigan Avenue that includes...
Apartment
2
2
5
$257/nt
$1,809/wk
$4,735/mth
$1,809/wk
$4,735/mth
Downtown Rooftop Penthouse+ 2Decks
The Penthouse features: - 2 bedrooms & 2.5 bath (sleeps 2~6 guests), 1400 sf living space & 800 sf rooftop decks - two...
The Penthouse features: - 2 bedrooms & 2.5 bath (sleeps 2~6 guests), 1400 sf living space & 800 sf rooftop decks - two...
Condo
2
2.5
7
$125/nt
$838/wk
$3,250/mth
$838/wk
$3,250/mth
Near Wrigley, Brown Line, Two
Writers retreat is an immaculate two bedroom apartment located less than a mile from Wrigley Field in a charming four unit...
Writers retreat is an immaculate two bedroom apartment located less than a mile from Wrigley Field in a charming four unit...
Apartment
2
1
7
$129/nt
$835/wk
$835/wk
Sp Suites - near Michigan Ave. BEST
Located in the heart of Chicago, these Corporate Furnished Apartments offer breathtaking views, rooftop deck with poolside...
Located in the heart of Chicago, these Corporate Furnished Apartments offer breathtaking views, rooftop deck with poolside...
Apartment
1
1
3
$150/nt
$1,109/wk
$3,082/mth
$1,109/wk
$3,082/mth
Downtown Breathtaking River- view
This condo is ON top of Chicago River, 4 blocks from Sears Tower, 2 blocks from train and bus stops. The Riverview Suite...
This condo is ON top of Chicago River, 4 blocks from Sears Tower, 2 blocks from train and bus stops. The Riverview Suite...
Condo
1
1
5
$149/nt
$943/wk
$3,258/mth
$943/wk
$3,258/mth
Great Deal, View, Hot Tub,
Close to Downtown & McCormick Place. 15 min by car or cab or 2- 3 train stops from everything that Chicago has to offer. Thi...
Close to Downtown & McCormick Place. 15 min by car or cab or 2- 3 train stops from everything that Chicago has to offer. Thi...
Apartment
3
1.5
6
$147/nt
$930/wk
$930/wk
Two Bedroom, Blue Line, Wrigley
Old Irving Loft is an economical, immaculately clean, near Wrigley, two bedroom upper available for vacation and executive...
Old Irving Loft is an economical, immaculately clean, near Wrigley, two bedroom upper available for vacation and executive...
Apartment
2
1
5
$129/nt
$835/wk
$835/wk
Beautiful Chicago Vacation Condo
Beautiful 3 Bed, 2 Bath Condo With Hardwood Floors Throughout, Granite Counters, 42" Custom Cabinetry, Stainless Steel...
Beautiful 3 Bed, 2 Bath Condo With Hardwood Floors Throughout, Granite Counters, 42" Custom Cabinetry, Stainless Steel...
Condo
3
2
6
$190/nt
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
Budget Rental- Beaches, Parks,
Pratt Shore another great Chicago Hotel Alternative, extended stay - temporary housing solution 8 story midrise near...
Pratt Shore another great Chicago Hotel Alternative, extended stay - temporary housing solution 8 story midrise near...
Condo
1
1
1
$66/nt
$500/wk
$1,400/mth
$500/wk
$1,400/mth
$129 per Bedroom* 2BR Condo Walk to
Beautiful, 2 bdrm, 2 bath, condo with 10 ft floor to ceiling windows and a balcony with views of the city and the lake....
Beautiful, 2 bdrm, 2 bath, condo with 10 ft floor to ceiling windows and a balcony with views of the city and the lake....
Condo
2
2
6
$214/nt
$1,500/wk
$4,200/mth
$1,500/wk
$4,200/mth
55th Floor 1 Bedroom Penthouse
This stylish, completely renovated Condominium offers spectacular views from the 55th floor of the Chicago skyline and Lakesho...
This stylish, completely renovated Condominium offers spectacular views from the 55th floor of the Chicago skyline and Lakesho...
Condo
1
1
4
$258/nt
Stylish, Hip & Nicely Decorated -
Amenities: - 24 Hour Door Attendant; - Professional Fitness Center; - Cardio Fitness Center; - Aerobics...
Amenities: - 24 Hour Door Attendant; - Professional Fitness Center; - Cardio Fitness Center; - Aerobics...
Apartment
0
1
3
$155/nt
$1,171/wk
$2,871/mth
$1,171/wk
$2,871/mth
**w**o**w** Heart Of Downtown**
Walk To Everything Downtown! Enjoy Stunning Views Of The City Skyline And Grant Park! One Of Few 3bd/2.5ba Units Right...
Walk To Everything Downtown! Enjoy Stunning Views Of The City Skyline And Grant Park! One Of Few 3bd/2.5ba Units Right...
Apartment
3
2.5
8
$280/nt
Wrigley 2 Room Suite Daily Complete
Wrigley suite - - - - 2 blocks from wrigleytfield- - 12 minutes to downtown - - - 2 rooms 400 sqft 2 ba w/ complementry...
Wrigley suite - - - - 2 blocks from wrigleytfield- - 12 minutes to downtown - - - 2 rooms 400 sqft 2 ba w/ complementry...
Bed & Breakfast
1
2
6
$56/nt
$159* 1br - Gorgeous Modern Condo
This gorgeous 1 bedroom has charm written all over it. Located in the heart of Chicago this beautifully furnished condo is...
This gorgeous 1 bedroom has charm written all over it. Located in the heart of Chicago this beautifully furnished condo is...
Condo
1
1
4
$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
$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* 3BR- New Brilliant
This beautiful contemporary duplex epitomizes excellence, elegance, and splendor. With modern custom- designed furniture...
This beautiful contemporary duplex epitomizes excellence, elegance, and splendor. With modern custom- designed furniture...
Home
3
2
8
$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
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
$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