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Chicagoland Vacation Rentals in Illinois

 

 
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Description
Type
Beds
Baths
Sleeps
Avg. Rate
Chicago Illinois Vacation Rentals - Living Room with a VIEW
55th Floor 1 Bedroom Penthouse
Chicago, Illinois
This stylish, completely renovated Condominium offers spectacular views from the 55th floor of the Chicago skyline and Lakesho...
Condo 
$258/nt
 
Chicago Illinois Vacation Rentals - Apartment
Sp Suites - Millennium Park
Chicago, Illinois
These Vacation Rentals are located in the New East Side, a mixed- use neighborhood east of Michigan Avenue that includes...
Apartment 
$257/nt
$1,809/wk
$4,735/mth
 
last minute dealreviews available
 
Chicago Illinois Vacation Rentals - Apartment
**w**o**w** Heart Of Downtown**
Chicago, Illinois
Walk To Everything Downtown! Enjoy Stunning Views Of The City Skyline And Grant Park! One Of Few 3bd/2.5ba Units Right...
Apartment 
2.5 
$280/nt
 
new property 
Chicago Illinois Vacation Rentals - Condo
Budget Rental- Beaches, Parks,
Chicago, Illinois
Pratt Shore another great Chicago Hotel Alternative, extended stay - temporary housing solution 8 story midrise near...
Condo 
$66/nt
$500/wk
$1,400/mth
 
last minute deal 
Chicago Illinois Vacation Rentals - Apartment
East Rogers Park - Evanston
Chicago, Illinois
This is our "budget rental" for Chicago Unit rents for: $1500 per month $85 per night for less than 7 nights booking,...
Apartment 
$85/nt
$585/wk
$1,338/mth
 
Chicago Illinois Vacation Rentals - Condo
Chicago Skyline View Condo
Chicago, Illinois
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 
 
pets allowednew property
 
Chicago Illinois Vacation Rentals - dining room
Two Bedroom, Blue Line, Wrigley
Chicago, Illinois
Old Irving Loft is an economical, immaculately clean, near Wrigley, two bedroom upper available for vacation and executive...
Apartment 
$129/nt
$835/wk
 
pets allowedreviews available
new property 
Chicago Illinois Vacation Rentals - Incredible City Skyline View from our deck
Great Deal, View, Hot Tub,
Chicago, Illinois
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 
1.5 
$147/nt
$930/wk
 
availability updated within last 30 daysreviews available
 
Chicago Illinois Vacation Rentals - Condo
Beautiful Chicago Vacation Condo
Chicago, Illinois
Beautiful 3 Bed, 2 Bath Condo With Hardwood Floors Throughout, Granite Counters, 42" Custom Cabinetry, Stainless Steel...
Condo 
$190/nt
 
reviews available 
Chicago Illinois Vacation Rentals - Livingroom with Skyline Views
$129 per Bedroom* 2BR Condo Walk to
Chicago, Illinois
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 
$214/nt
$1,500/wk
$4,200/mth
 
availability updated within last 30 daysreviews available
 
Chicago Illinois Vacation Rentals - pool
Stylish, Hip & Nicely Decorated -
Chicago, Illinois
Amenities: - 24 Hour Door Attendant; - Professional Fitness Center; - Cardio Fitness Center; - Aerobics...
Apartment 
$155/nt
$1,171/wk
$2,871/mth
 
reviews available 
Chicago Illinois Vacation Rentals - Apartment
Sp Suites - near Michigan Ave. BEST
Chicago, Illinois
Located in the heart of Chicago, these Corporate Furnished Apartments offer breathtaking views, rooftop deck with poolside...
Apartment 
$150/nt
$1,109/wk
$3,082/mth
 
last minute dealreviews available
 
Chicago Illinois Vacation Rentals - Condo Building
Downtown Breathtaking River- view
Chicago, Illinois
This condo is ON top of Chicago River, 4 blocks from Sears Tower, 2 blocks from train and bus stops. The Riverview Suite...
Condo 
$149/nt
$943/wk
$3,258/mth
 
availability updated within last 30 dayslast minute deal
reviews available 
Chicago Illinois Vacation Rentals - Writers' Retreat Living Room
Near Wrigley, Brown Line, Two
Chicago, Illinois
Writers retreat is an immaculate two bedroom apartment located less than a mile from Wrigley Field in a charming four unit...
Apartment 
$129/nt
$835/wk
 
availability updated within last 30 dayspets allowed
new property 
Chicago Illinois Vacation Rentals - WRIGLEY CUBS SUITE
Wrigley 2 Room Suite Daily Complete
Chicago, Illinois
Wrigley suite - - - - 2 blocks from wrigleytfield- - 12 minutes to downtown - - - 2 rooms 400 sqft 2 ba w/ complementry...
Bed & Breakfast 
$56/nt
 
new property 
Chicago Illinois Vacation Rentals - River City Building
Downtown Rooftop Penthouse+ 2Decks
Chicago, Illinois
The Penthouse features: - 2 bedrooms & 2.5 bath (sleeps 2~6 guests), 1400 sf living space & 800 sf rooftop decks - two...
Condo 
2.5 
$125/nt
$838/wk
$3,250/mth
 
availability updated within last 30 dayslast minute deal
reviews available 
Chicago Illinois Vacation Rentals - Front View
China Doll Guest House
Chicago, Illinois
In Chicago's Lincoln Park neighborhood, China Doll offers complete self- contained apartment suites with private entrances....
Apartment 
$239/nt
$1,575/wk
 
pets allowedreviews available
 
Chicago Illinois Vacation Rentals - Steps To Navy Pier - Beaches, Shops, Restaurants, Night Life and More!
Location! Location! Location! Navy
Chicago, Illinois
Location Location Location! Can't Beat It! Set In The Heart Of Downtown Chicago, Our Chicago Apt Is Ideally...
Condo 
$265/nt
 
last minute dealreviews available
 
Chicago Illinois Vacation Rentals - Living Room
$129 per Bedroom* 4BR- Contemporary
Chicago, Illinois
Sleek, new home.... Features include: Italian Cabinetry and Faucets, Professional Grade Stainless Steel apps, Thick granite,...
Home 
10 
 
availability updated within last 30 daysreviews available
 
Chicago Illinois Vacation Rentals - Condo
$89 per Bedroom*3BR- Graystone
Chicago, Illinois
This is an amazing graystone home in historic Wrigley neighborhood. The house has been completely revamped to meet all the...
Condo 
 
availability updated within last 30 days 
Chicago Illinois Vacation Rentals - Condo
$99 per Bedroom*7BR Luxurious Mansion
Chicago, Illinois
Timeless elegance with all the luxuries you can imagine, oversize lot in Blaine school district, 7 bedrooms, 5 en- suite...
Condo 
18 
 
availability updated within last 30 days 
Chicago Illinois Vacation Rentals - Condo
$89 Per Bedroom* 6br- New Duplex
Chicago, Illinois
This brand new 6- bedroom will blow you away. The 1600 sq. foot interior is decked with contemporary and traditional finishes....
Condo 
16 
 
availability updated within last 30 days 
Chicago Illinois Vacation Rentals - Kitchen
$99 per Bedroom* 3BR- New Brilliant
Chicago, Illinois
This beautiful contemporary duplex epitomizes excellence, elegance, and splendor. With modern custom- designed furniture...
Home 
 
availability updated within last 30 days 
Chicago Illinois Vacation Rentals - Condo
$159* 1br - Gorgeous Modern Condo
Chicago, Illinois
This gorgeous 1 bedroom has charm written all over it. Located in the heart of Chicago this beautifully furnished condo is...
Condo 
 
availability updated within last 30 days 
Chicago Illinois Vacation Rentals - 30 E. Huron
This penthouse puts you in the heart
Chicago, Illinois
These units have recently been renovated and includes hard wood floors, Granite countertops, Stainless steel appliances...
Condo 
 
reviews available 
 
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