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 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.

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
Hyatt Regency McCormick Place - Hotel in Chicago
800 Bedrooms
location. Located in the south loop of chicago, ill., the hyatt regency mccormick place is connected via skybridge to the adjacent mccormick place convention center. burnham park and harbor is locate ...Read Full Description
ID: 64648
The Blackstone, A Renaissance Hotel - Hotel in Chicago
332 Bedrooms
Location. <ul><li>the blackstone is located in chicago, ill.</li> <li>adjacent to grant park</li> <li>two miles from ...Read Full Description
Check to Inquire *
ID: 64648
Wyndham Chicago - Hotel in Chicago
417 Bedrooms
Location. The wyndham chicago hotel is located one block from north michigan avenue's specialty boutiques in chicago, ill. this property stands three blocks from lake michigan and six blocks from the ...Read Full Description
ID: 64648
The Silversmith Hotel - Hotel in Chicago
143 Bedrooms
Location. The silversmith hotel & suites is located in chicago, ill., in the center of the loop area and financial district. the hotel stands at the corner of wabash and monroe streets, two blocks ...Read Full Description
ID: 64648
Chicago O'Hare Garden Hotel - Hotel in Chicago
122 Bedrooms
Location. <ul><li>the chicago o'hare garden hotel is located in chicago, ill.</li> <li>two-and-one-half blocks from an elevated train station&am ...Read Full Description
ID: 64648
Hotel Sax Chicago - Hotel in Chicago
367 Bedrooms
Location. The hotel sax chicago is stationed within chicago's (ill.) marina city complex, just two blocks north of the chicago loop business and financial district and one-half block from the chicago ...Read Full Description
ID: 64648
Homewood Suites by Hilton Chicago Downtown - Hotel in Chicago
233 Bedrooms
Location. <ul><li> the homewood suites is located in chicago, ill.</li> <li>one block from north michigan avenue</li> <li&a ...Read Full Description
ID: 64648
W Chicago City Center - Hotel in Chicago
369 Bedrooms
Location. The w chicago city center is anchored in the center of chicago's (ill.) downtown loop business district. the sears tower rises one block from the hotel, while the theater district is located ...Read Full Description
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ID: 64648
OAKWOOD CHICAGO - Hotel in Chicago
304 Bedrooms
Year built - 1970
additional property description -
 oakwood chicago corporate housing is gold coast and
 river north living at its finest. Oakwood chicago
 provides el ...Read Full Description
ID: 64648
Club Quarters, Central Loop - Hotel in Chicago
322 Bedrooms
Location. The club quarters, central loop is located in chicago, ill., adjacent to the rookery building and one block from the chicago board of trade. this hotel stands two miles from the magnificent ...Read Full Description
ID: 64648
Embassy Suites Chicago Downtown - Lakefront - Hotel in Chicago
455 Bedrooms
location. The embassy suites chicago downtown lakefront is the closest of all the downtown chicago, ill., hotels to the lake michigan lakefront, only three blocks away. the blue-line trolley station ...Read Full Description
ID: 64648
THE STANDARD CLUB - Hotel in Chicago
60 Bedrooms
Founded in 1869 the standard club is located in the
heart of chicagos business legal finamcial and
cultural districts within walking distance to most
major companies a 5 star p ...Read Full Description
ID: 64648
Marriott Chicago Midway Airport - Hotel in Chicago
197 Bedrooms
Location. The marriott chicago midway airport stands one-half mile south of chicago midway airport in chicago, ill. downtown chicago is eight miles away. the hotel is five miles from toyota park. hote ...Read Full Description
ID: 64648
Hilton Chicago O'Hare Airport - Hotel in Chicago
858 Bedrooms
Location. The hilton chicago o'hare airport is connected to chicago o'hare international airport in chicago, ill. the donald e. stephens convention center and the rosemont theatre stand two miles from ...Read Full Description
ID: 64648
Courtyard by Marriott Chicago Magnificent Mile - Hotel in Chicago
306 Bedrooms
Location. Rising 23 stories above the streets of chicago, ill., the courtyard magnificent mile is one block from the boutiques of the magnificent mile and four blocks from the activities of lake michi ...Read Full Description
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*Traveling Dates:

Flexible Dates
1+ (79)
3+ (72)
6+ (68)
11+ (67)

(vacation rentals only)
Studio (1)
1 (11)
2 (2)
4+ (107)

Vacation Rental Types:
Apartment (9)
Home (2)

Lodging Types:
Hotels (122)
Vacation Rentals (12)

Location Attributes:
Lakefront (2)
Near beach (4)
Waterfront (1)
Beachfront (1)

Sauna (32)
Coffee Maker (11)
Full Kitchen (11)
Air Conditioning (8)
Refrigerator (6)
TV/VCR (6)

Things To Do:
Restaurants (5)
Museums (4)
Theaters / Cinemas (5)
Sightseeing (5)
Spa (2)
Swimming (4)

Special Features:
Children Welcome (134)
Smoking Permitted (129)
Pet friendly (133)
Handicap accesibility (100)

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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