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 56 | 1 2 3 Next |
Description
Type
Beds
Baths
Sleeps
Avg. Rate
Chicago Southport Suite , A Luxury
Pay For 4 Nights And Get The 5th Night Free!!!!location: Lakeview, North Side, Chicago, Illinois, Usa (12.4 Mi- O'hare,...
Pay For 4 Nights And Get The 5th Night Free!!!!location: Lakeview, North Side, Chicago, Illinois, Usa (12.4 Mi- O'hare,...
Condo
2
1
6
$195/nt
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
$148/nt
$1,010/wk
$3,298/mth
$1,010/wk
$3,298/mth
Roscoe Village Row House w/ Garage
2008 gut rehabbed corner lot single family brick row house in the middle of Roscoe Village. One of Chicago's best neighborhoods...
2008 gut rehabbed corner lot single family brick row house in the middle of Roscoe Village. One of Chicago's best neighborhoods...
Home
4
3.5
6
Downtown Rooftop Penthouse+ 2Decks
The Penthouse Features: - 2 Bedrooms & 2.5 Bath (sleeps 2~7 Guests), 1400 Sf Living Space & 800 Sf Rooftop Decks - Two...
The Penthouse Features: - 2 Bedrooms & 2.5 Bath (sleeps 2~7 Guests), 1400 Sf Living Space & 800 Sf Rooftop Decks - Two...
Condo
2
2.5
7
$211/nt
$1,166/wk
$3,832/mth
$1,166/wk
$3,832/mth
Millennium Park 2 bedrooms, 2
These Vacation Rentals are situated in the New East Side, Chicago’s newest neighborhood, a prime area of downtown Chicago....
These Vacation Rentals are situated in the New East Side, Chicago’s newest neighborhood, a prime area of downtown Chicago....
Condo
2
2
5
$200/nt
$1,308/wk
$3,494/mth
$1,308/wk
$3,494/mth
Feb Cleaning Waived! - 2BR- Fantasti
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
$242/nt
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
$160/nt
$974/wk
$974/wk
2BR Condo Walk to Mag Mile!
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
$1,500/wk
$4,200/mth
$4,200/mth
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
$140/nt
$1,043/wk
$3,049/mth
$1,043/wk
$3,049/mth
Feb Cleaning Waived! - 4br-
Sleek, new home.... Features include: Italian Cabinetry and Faucets, Professional Grade Stainless Steel apps, Thick granite,...
Sleek, new home.... Features include: Italian Cabinetry and Faucets, Professional Grade Stainless Steel apps, Thick granite,...
Home
4
4
10
$503/nt
$4,200/mth
$4,200/mth
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
Feb Cleaning Waived! 6BR Mansion in
Exclusions: Elite Chicago Rentals reserves the right to change prices without notice. Promotional prices are valid between...
Exclusions: Elite Chicago Rentals reserves the right to change prices without notice. Promotional prices are valid between...
Home
6
4.5
18
$789/nt
Feb Cleaning Waived! - 3br-
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
$299/nt
Location! Location! Location! Navy
Location Location Location! Can't Beat It! Views Views Views! Breathtaking Lake And City Views!! Looks...
Location Location Location! Can't Beat It! Views Views Views! Breathtaking Lake And City Views!! Looks...
Condo
2
2
6
$231/nt
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
**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
Feb Cleaning Waived! - 2BR Near
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
$313/nt
$1,600/wk
$3,500/mth
$1,600/wk
$3,500/mth
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
1
1
3
$177/nt
$1,247/wk
$2,994/mth
$1,247/wk
$2,994/mth
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
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
Convenient, Homey in Lakeview/Wrigle
Writers' Retreat is an immaculate two bedroom apartment less than a mile from Wrigley Field, home of the Chicago Cubs. Locate...
Writers' Retreat is an immaculate two bedroom apartment less than a mile from Wrigley Field, home of the Chicago Cubs. Locate...
Apartment
2
1
7
1BR - Gorgeous Modern Condo Mag
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
Convenient, Comfy Home Away from
Old Irving Loft is a two bedroom upper unit available for vacation and executive rentals. Situated in a convenient location...
Old Irving Loft is a two bedroom upper unit available for vacation and executive rentals. Situated in a convenient location...
Apartment
2
1
5
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
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
$695/nt
$3,705/wk
$11,157/mth
$3,705/wk
$11,157/mth