Chicago Vacation Rentals in Illinois
Our Chicago vacation rentals section includes the apartment, guesthouse, home, 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 Lemont (22 miles), Plainfield (33 miles), Michigan City (41 miles), Union Pier (50 miles), and Sandwich (53 miles) for additional vacation rental options.
Results 1 - 25 of 38
Description
Type
Beds
Baths
Sleeps
Avg. Rate
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
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
$1,400/wk
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
$3,500/mth
$1,250/wk
$3,500/mth
Stylish, Hip & Nicely Decorated 2
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
2
2
2
$285/nt
$1,681/wk
$5,203/mth
$1,681/wk
$5,203/mth
55th Floor 1 Bedroom Penthouse -
This stylish, completely renovated Condominium offers spectacular views from the 55th floor of the Chicago skyline and Lakeshore....
This stylish, completely renovated Condominium offers spectacular views from the 55th floor of the Chicago skyline and Lakeshore....
Condo
1
1
4
$258/nt
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
Imaculate View with 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
6
$195/nt
$1,225/wk
$3,200/mth
$1,225/wk
$3,200/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 -...
The Penthouse features: - 2 bedrooms & 2.5 bath (sleeps 2~6 guests), 1400 sf living space & 800 sf rooftop decks -...
Condo
2
2.5
6
$251/nt
$1,600/wk
$4,500/mth
$1,600/wk
$4,500/mth
Great City Views - 45th Floor
Newer unit with super city & lake views, overlooking Grant Park, near Millennium Park, off Lake Shore Drive, walk to...
Newer unit with super city & lake views, overlooking Grant Park, near Millennium Park, off Lake Shore Drive, walk to...
Apartment
2
2
4
$295/nt
Best Value for $, Hot Tub, Parking
This is an amazing rental at a great value. Don't be fooled by the low price, this unit is every bit as nice or more expensive...
This is an amazing rental at a great value. Don't be fooled by the low price, this unit is every bit as nice or more expensive...
Apartment
3
1.5
6
$158/nt
$887/wk
$887/wk
Magnificent Mile 1 BR - near Oprah's
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
$225/nt
$1,575/wk
$2,600/mth
$1,575/wk
$2,600/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
$253/nt
$1,662/wk
$3,620/mth
$1,662/wk
$3,620/mth
Penthouse Suite
23rd Floor Penthouse Suite - Downtown Chicago Lakefront, Terrace, Historic Prairie District, Private, Safe, 24HR...
23rd Floor Penthouse Suite - Downtown Chicago Lakefront, Terrace, Historic Prairie District, Private, Safe, 24HR...
Condo
3
2.5
6
$490/nt
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
10
$189/nt
$2,800/mth
$2,800/mth
Modern 4 Level Home, Minutes from
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
$344/nt
$2,700/wk
$8,000/mth
$2,700/wk
$8,000/mth
Beautiful Executive APT.
Fully Furnished, Cable TV, Secure Intercom, All Utilities, Complimentary Coffee. Full size sofa bed in lounge sleeps...
Fully Furnished, Cable TV, Secure Intercom, All Utilities, Complimentary Coffee. Full size sofa bed in lounge sleeps...
Apartment
1
1
4
$136/nt
$800/wk
$2,700/mth
$800/wk
$2,700/mth
Chicago Guest House
Chicago Guest House on Lakewood Avenue 1 Stately Graystone with 3 Separate Apartments Featured: Wrigley Suite 4bdrm/ 2bth...
Chicago Guest House on Lakewood Avenue 1 Stately Graystone with 3 Separate Apartments Featured: Wrigley Suite 4bdrm/ 2bth...
Guesthouse
4
2
8
$495/nt
$3,118/wk
$3,118/wk
Luxury Home Rental in Wrigleyville
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
$767/nt
$4,705/wk
$18,350/mth
$4,705/wk
$18,350/mth
The Franklin Flat
The franklin flat has vintage charm with modern updates. This 2 bedroom, one bathroom, 3rd floor walk up has Soaring 12'ceilings...
The franklin flat has vintage charm with modern updates. This 2 bedroom, one bathroom, 3rd floor walk up has Soaring 12'ceilings...
Condo
2
1
5
$232/nt
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
Downtown Condo w/ Gorgeous View
This Chicago Downtown Riverview Suite features: - 1 bedroom & 1 bath (sleeps 2~5 guests), kitchen, living room, make...
This Chicago Downtown Riverview Suite features: - 1 bedroom & 1 bath (sleeps 2~5 guests), kitchen, living room, make...
Condo
1
1
4
$174/nt
$1,200/wk
$3,600/mth
$1,200/wk
$3,600/mth
The Wayne Manor
Gather your group and get ready to live in comfort! Lots of open space, good size bedrooms and bathrooms. This Beautiful...
Gather your group and get ready to live in comfort! Lots of open space, good size bedrooms and bathrooms. This Beautiful...
Home
4
4
10
$700/nt
$3,100/wk
$15,000/mth
$3,100/wk
$15,000/mth
Pratt Shore - 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
HistoricMansion in Downtown Chicago
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
8
$150/nt
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