Chicago Vacation Rentals in Illinois
Our Chicago vacation rentals section includes the home, apartment, 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 Michigan City (41 miles), New Buffalo (47 miles), Union Pier (50 miles), Sawyer (55 miles), and Twin Lakes (57 miles) for additional vacation rental options.
| Results 1 - 25 of 67 | 1 2 3 Next |
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
Beautiful Furnished Condo
$150 nightly or $900 per week, Corporate rental or Vacation Condo Beautiful furnished lake Michigan view from the 27th...
$150 nightly or $900 per week, Corporate rental or Vacation Condo Beautiful furnished lake Michigan view from the 27th...
Condo
2
2
4
$150/nt
$900/wk
$3,000/mth
$900/wk
$3,000/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
20
$265/nt
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
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
Wicker Park Corporate / Vacation
- Huge 2200 sq- feet condo in the middle of fun Wicker Park neighborhood - Ideal for a family or friends on vacation/work...
- Huge 2200 sq- feet condo in the middle of fun Wicker Park neighborhood - Ideal for a family or friends on vacation/work...
Condo
3
2
7
$192/nt
$1,223/wk
$1,223/wk
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. Th...
Close to Downtown & McCormick Place. 15 min by car or cab or 2- 3 train stops from everything that Chicago has to offer. Th...
Apartment
3
1.5
6
$159/nt
$956/wk
$956/wk
Great City Views - 45th Floor (Best
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
$224/nt
$1,665/wk
$1,665/wk
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
* Nancy's! 4br 3 Level Brick Home.
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
$549/nt
$2,999/wk
$2,999/wk
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
$767/nt
$4,705/wk
$18,350/mth
$4,705/wk
$18,350/mth
* Nancy's! Modern 2br, 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
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
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
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
$262/nt
$1,780/wk
$5,019/mth
$1,780/wk
$5,019/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
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
$154/nt
$1,143/wk
$3,164/mth
$1,143/wk
$3,164/mth
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
* Nancy's! 4brm - Contemporary
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
$549/nt
$3,199/wk
$3,199/wk
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
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
8
$185/nt
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
7
$233/nt
$1,476/wk
$4,323/mth
$1,476/wk
$4,323/mth
Downtown Breathtaking River- view
The Riverview Suite features: - 1 bedroom & 1 bath (sleeps 2~5 guests), kitchen, living room, make up area. - breathtak...
The Riverview Suite features: - 1 bedroom & 1 bath (sleeps 2~5 guests), kitchen, living room, make up area. - breathtak...
Condo
1
1.5
5
$146/nt
$974/wk
$3,213/mth
$974/wk
$3,213/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
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