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
Doubletree Hotel Chicago Magnificent Mile - Hotel in Chicago
495 Bedrooms
Location.doubletree chicago magnificent mile is located in the northern sector of downtown chicago, ill. This property stands two blocks from the magnificent mile and lake michigan. hotel features. th ...Read Full Description
ID: 64648
Ambassador East Hotel - Hotel in Chicago
278 Bedrooms
Location. The ambassador east hotel is located two blocks from lake michigan in chicago, ill. rush street restaurants and bars are positioned three blocks away. the magnificent mile and north avenue b ...Read Full Description
ID: 64648
Chicago's Essex Inn - Hotel in Chicago
254 Bedrooms
Location. <ul><li>the chicago's essex inn is located in chicago, ill.</li> <li>across the street from grant park</li> <li&a ...Read Full Description
ID: 64648
Swissotel - Chicago - Hotel in Chicago
632 Bedrooms
Location. The swissotel-chicago soars 43 stories alongside the chicago river in downtown chicago, ill. this property is located three blocks from lake michigan and the lakefront running path. an under ...Read Full Description
Check to Inquire *
ID: 64648
The Drake Hotel - Hotel in Chicago
535 Bedrooms
Location. The drake hotel is located in downtown chicago, ill., adjacent to michigan avenue's renowned shops and restaurants. this property stands three blocks from the john hancock building and water ...Read Full Description
ID: 64648
435 Bedrooms
Set atop water tower place, high above north michigan
avenue, and featuring lavish decor, exquisite furnishings
and one of chicago*s finest contemporary french restaurants,
the ...Read Full Description
ID: 64648
Holiday Inn O'Hare - Hotel in Chicago
242 Bedrooms
Location. <ul><li>the holiday inn chicago o'hare is located in chicago, ill. </li> <li>two miles from o'hare international airport</li&am ...Read Full Description
ID: 64648
The Talbott Hotel - Hotel in Chicago
149 Bedrooms
Location. One of the true treasures of chicago, ill., the talbott hotel is a boutique-style hotel built in 1927. the hotel is within walking distance of the eclectic shops and boutiques of the magnifi ...Read Full Description
ID: 64648
Omni Chicago Hotel - Hotel in Chicago
347 Bedrooms
Location. The omni chicago hotel is located adjacent to michigan avenue's magnificent mile in chicago, ill. this property stands one block from rush street shops and entertainment. american girl place ...Read Full Description
ID: 64648
Marriott Chicago at Medical District/UIC - Hotel in Chicago
114 Bedrooms
Location. The marriott chicago at medical district/uic is located across the street from rush university medical center and the university of illinois campus in chicago, ill. the hotel stands three bl ...Read Full Description
ID: 64648
Best Western Grant Park - Hotel in Chicago
172 Bedrooms
Location. <ul><li>the best western grant park is located in chicago, ill.</li> <li>one-half mile from shedd aquarium</li> < ...Read Full Description
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ID: 64648
Hotel 71 - Hotel in Chicago
454 Bedrooms
Location. The hotel 71 overlooks the riverwalk at the busy intersection of wacker drive and michigan avenue in chicago, ill. this property stands three blocks across the river from magnificent mile sh ...Read Full Description
ID: 64648
Howard Johnson Downtown - Hotel in Chicago
71 Bedrooms
The howard johnson downtown, chicago, ill., is located less than 12 miles from chicago midway airport and within three miles of both northwestern university the university of illinois at chicago campu ...Read Full Description
Check to Inquire *
ID: 64648
The James - Hotel in Chicago
297 Bedrooms
location. Located in downtown chicago, ill., this boutique hotel is less than one block from michigan avenue and four blocks from the john hancock building, navy pier and historic water tower. tribun ...Read Full Description
ID: 64648
The Willows Hotel - Hotel in Chicago
55 Bedrooms
Location. <ul><li> the willows hotel is located in chicago, ill.</li> <li>two blocks from lake michigan</li> <li>one ...Read Full Description
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Smart Search

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*Traveling Dates:

Flexible Dates
(vacation rentals only)
4+ (64)

Vacation Rental Types:
Home (1)

Lodging Types:
Hotels (67)
Vacation Rentals (1)

Sauna (17)
Coffee Maker (6)
Full Kitchen (5)
Air Conditioning (2)
TV/VCR (1)

Special Features:
Children Welcome (68)
Smoking Permitted (68)
Pet friendly (68)
Handicap accesibility (56)

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Oak Park (2)
Bedford Park (2)
Bridgeview (1)
Melrose Park (1)
Franklin Park (2)
Calumet Park (1)
Evanston (3)
Schiller Park (4)
Skokie (3)
Alsip (3)
Northlake (1)
Niles (2)
Morton Grove (1)
Oak Brook (4)
Elmhurst (4)
Burr Ridge (1)
Willowbrook (3)
Oakbrook (2)
Oakbrook Terrace (3)
Des Plaines (7)
South Holland (2)
Westmont (3)
Addison (3)
Lombard (6)
Orland Park (1)

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