Chicago Vacation Rentals

Welcome to Chicago. Scroll down this page to find your favorite travel destination in Chicago and browse our extensve inventory of accommodations in Chicago. Leisure travelers planning their family vacations can get offers directly from owners of Chicago vacation homes or houses in Chicago. Sometimes these single rental units are referred to as Chicago cabins or Chicago villas. Other popular lodging options include vacation rentals in Chicago, Chicago apartments and condos in Chicago. For business travelers we offer several convenient hotels in Chicago or small boutique hotels in Chicago area, many with the ability to book online. If you are planning a romantic getaway in Chicago, we highy recommend our unique inventory of bed and breakfasts in Chicago. B&Bs can also referred as small country inns in Chicago.

Finding the perfect vacation rental property can be very time consuming. Unlike many other sites out there that demand travelers (like you) to invest countless hours browsing though each vacation rental listing, at Rentalo.com we make it easy for travelers to find best Chicago vacation rentals using our free inquiry service or Chicago lodging locator service. Save time searching for Chicago rental vacations and Chicago accommodations! Simply click the "Inquire Now" button, complete a short inquiry form, and within minutes you will start receiving multiple offers from Chicago vacation home rentals owners as well as from Chicago resorts, Chicago cabin rentals, and Chicago vacation homes.

Let Rentalo help you find the perfect place to stay for your next family vacation in Illinois area. Our engine will match your specific inquiry criteria with each Chicago vacation rental listing, Chicago vacation house or Chicago villa in our Chicago rental vacations inventory. Finding Chicago vacation rentals by owner is easy with our free inquiry service. However, you can also browse our inventory of Chicago accommodation listings (as listed below) or use the SmartSearch tool to narrow down your search for Chicago lodging in Illinois.

Popular Searches in Chicago

Enter your travel dates and number of people traveling (sleeps) and use one of the following search options:

  1. Inquire on ALL Vacation Rentals in Chicago. Click "Inquire Now" (Fastest Option - Receive the most Offers)
  2. Inquire on Selected Vacation Rentals in Chicago. Click "Check to inquire", then click "Inquire Now" (Time-Saving Option - Receive Offers from Selected Properties)
  3. Inquire only on a Specific Chicago Vacation Rental (Take the time to review each property - Receive an offer on the Property you like)
Inquire on multiple properties - Save time! Inquire, Compare offers, and Book.


ID: 64648
W Chicago Lakeshore - Hotel in Chicago
 
578 Bedrooms
Location. The w chicago lakeshore, located in chicago, ill., rises 33 stories above the scenic shores of lake michigan. this hotel stands two blocks from ontario beach, navy pier and northwestern univ ...Read Full Description
ID: 64648
FOUR SEASONS CHICAGO - Hotel in Chicago
 
343 Bedrooms

four seasons hotel chicago is an ideal setting for corporate
leisure and family travel with its multimillion dollars guest
room renovation nearly complete and fully renovated ...Read Full Description
ID: 64648
Congress Plaza Hotel - Hotel in Chicago
 
850 Bedrooms
Location. <ul><li>the congress plaza hotel is located in chicago, ill.</li> <li>across the street from grant park</li> <li& ...Read Full Description
ID: 64648
The Fairmont Chicago - Hotel in Chicago
 
687 Bedrooms
Location. The fairmont chicago is located in chicago, ill., one block from millennium park. this property stands less than one mile from the art institute of chicago and the magnificent mile. hotel fe ...Read Full Description
ID: 64648
Hilton Suites Chicago Magnificent Mile - Hotel in Chicago
 
345 Bedrooms
Location. Located one block from the famed shopping of the magnificent mile and the john hancock center, and two blocks from oak street beach, the hilton suites chicago magnificent mile is an ideal de ...Read Full Description
Check to Inquire *
ID: 64648
Affinia Chicago - Hotel in Chicago
 
140 Bedrooms
Location. The downtown affinia chicago is located in the streeterville neighborhood of chicago, ill. this property stands one block from michigan avenue magnificent mile shops and is positioned two bl ...Read Full Description
ID: 64648
Embassy Suites Chicago Downtown - Hotel in Chicago
 
358 Bedrooms
location. The embassy suites chicago downtown (ill.) is located four blocks north of the chicago loop business and theater districts. magnificent mile shopping at north michigan avenue is three block ...Read Full Description
Check to Inquire *
ID: 64648
Hotel Blake - Hotel in Chicago
 
162 Bedrooms
Location. Located in the historic printers row district of downtown chicago, ill., this landmark hotel occupies the 19th-century morton salt building, renovated in early 2006. the chicago loop financi ...Read Full Description
ID: 64648
Seneca Hotel & Suites - Hotel in Chicago
 
190 Bedrooms
Location. <ul><li>the seneca hotel and suites is located in chicago, ill.</li> <li>adjacent to john hancock center</li> <li ...Read Full Description
Check to Inquire *
ID: 64648
Raffaello Hotel - Hotel in Chicago
 
173 Bedrooms
Location. The raffaello hotel is located in the gold coast area of downtown chicago, ill. the property is one block from michigan avenue shopping at the magnificent mile. lake michigan and the rush st ...Read Full Description
ID: 64648
Millennium Knickerbocker - Hotel in Chicago
 
306 Bedrooms
Location. The millennium knickerbocker stands one-half block from the magnificent mile shops in chicago, ill. oak street boutiques, the john hancock center and water tower place are located two blocks ...Read Full Description
Check to Inquire *
ID: 64648
Park View Hotel - Hotel in Chicago
 
224 Bedrooms
Location. <ul><li>the park view hotel chicago is located in chicago, ill.</li> <li>across the street from north avenue beach</li> ...Read Full Description
ID: 64648
The Tremont Chicago - Hotel in Chicago
 
130 Bedrooms
Location. <ul><li>the tremont chicago is located in chicago, ill. </li> <li>one-half block from michigan avenue shops</li> &lt ...Read Full Description
ID: 64648
City Suites Hotel - Hotel in Chicago
 
45 Bedrooms
Location. <ul><li> the city suites hotel is located in chicago, ill.</li> <li>one-half mile from wrigley field and lake michigan</li& ...Read Full Description
ID: 64648
Sutton Place Hotel by the Magnificent Mile - Hotel in Chicago
 
246 Bedrooms
Location. The sutton place hotel soars high above tree-lined streets in chicago's (ill.) gold coast neighborhood. this property showcases classic architecture with traces of gothic influence. located ...Read Full Description
Inquire on multiple properties - Save time! Inquire, Compare offers, and Book.


Smart Search


*Traveling Dates:

Flexible Dates
*Sleeps:
1+ (77)
3+ (73)
6+ (69)
11+ (67)

Bedrooms:
(vacation rentals only)
Studio (2)
1 (7)
2 (2)
4+ (108)

Vacation Rental Types:
Apartment (7)
Home (2)

Lodging Types:
Hotels (121)
Vacation Rentals (10)

Location Attributes:
Lakefront (3)
Near water (1)
Near beach (5)
Waterfront (2)
Beachfront (1)
More...

Amenities:
Sauna (32)
Coffee Maker (13)
Full Kitchen (12)
Air Conditioning (10)
Refrigerator (7)
TV/VCR (8)
More...

Things To Do:
Restaurants (7)
Museums (6)
Theaters / Cinemas (6)
Sightseeing (7)
Spa (3)
Swimming (5)
More...

Special Features:
Children Welcome (131)
Smoking Permitted (125)
Pet friendly (129)
Handicap accesibility (96)

Add these vicinities to my search:
Note: Use Search Destination box (above) to browse listings in these vicinities.
Oak Park (2)
Bedford Park (6)
Bridgeview (2)
Oak Lawn (1)
Melrose Park (1)
Franklin Park (2)
Calumet Park (1)
Evanston (4)
Schiller Park (6)
Skokie (5)
Alsip (3)
Northlake (1)
Niles (3)
Morton Grove (2)
Oak Brook (6)
Elmhurst (7)
Burr Ridge (3)
Willowbrook (6)
Oakbrook (2)
Oakbrook Terrace (7)
Des Plaines (9)
South Holland (2)
Westmont (4)
Addison (3)
Lombard (10)
Orland Park (3)

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