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.

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: 384874
CHIClittleSUITE Near McCormick Place - Vacation Rental in Chicago
From USD125 nt
1 Bedrooms
Sleeps 1
Located within a 10mins walking distance to mccormick place, the chic little suite occupies the entire second level of my open air duplex loft. The suite has an en suite bathroom (equipped with towels ...Read Full Description
ID: 390545
Chicago Loop Luxury Jr. One Bedroom - Vacation Rental in Chicago
From USD180 nt
1 Bedrooms
Sleeps 4
31 night minimum stay. An on-site pool highlights this modern apartment in chicago's theatre district. the property is 1,650 feet from iconic willis tower and just 10 minutes' walk from millennium par ...Read Full Description
ID: 390545
Chicago Loop Luxury One Bedroom - Vacation Rental in Chicago
From USD205 nt
1 Bedrooms
Sleeps 4
31 night minimum stay. An on-site pool highlights this modern apartment in chicago's theatre district. the property is 1,650 feet from iconic willis tower and just 10 minutes' walk from millennium par ...Read Full Description
ID: 64648
Kinzie Hotel Chicago - Hotel in Chicago
 
1 Bedrooms
Sleeps 5
Exploration. Discovery. authenticity. chicago starts here. located in the heart of the vibrant river north district, kinzie hotel embodies the adventurous spirit of chicago. named after the renowned c ...Read Full Description
ID: 64648
Four Points by Sheraton Chicago Downtown - Magnifi - Hotel in Chicago
 
1 Bedrooms
Location. <ul><li>the four points by sheraton chicago downtown - magnificent mile is located in chicago, ill.</li> <li>one-quarter mile from the ...Read Full Description
ID: 64648
Trump International Hotel & Tower Chicago - Hotel in Chicago
 
1 Bedrooms
Location.the trump international hotel and tower is located one block from the magnificent mile, the michigan avenue shopping district, in chicago, ill. The hotel is one-half mile from daley plaza, ce ...Read Full Description
ID: 64648
Central Loop Hotel - Hotel in Chicago
 
1 Bedrooms
Location. The central loop hotel is located in the historic loop, chicago's business and cultural district. the hotel is located three blocks from the sears tower, five blocks from the art institute, ...Read Full Description
Inquire on multiple properties - Save time! Inquire, Compare offers, and Book.


Smart Search


Bedrooms: 1 Remove 1
(vacation rentals only)

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*Traveling Dates:

Flexible Dates
*Sleeps:
1+ (4)
3+ (3)

Vacation Rental Types:
Apartment (2)
Home (1)

Lodging Types:
Hotels (4)
Vacation Rentals (3)

Location Attributes:
Lakefront (1)
Near beach (3)
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Amenities:
Sauna (2)
Coffee Maker (3)
Full Kitchen (3)
Air Conditioning (4)
Refrigerator (3)
TV/VCR (3)
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Things To Do:
Restaurants (3)
Museums (3)
Theaters / Cinemas (3)
Sightseeing (3)
Spa (1)
Swimming (2)
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Special Features:
Children Welcome (7)
Smoking Permitted (4)
Pet friendly (6)
Handicap accesibility (4)

Add these vicinities to my search:
Note: Use Search Destination box (above) to browse listings in these vicinities.
Bedford Park (1)
Bridgeview (1)
Schiller Park (2)
Skokie (1)
Elmhurst (2)
Burr Ridge (1)
Willowbrook (1)
Des Plaines (2)
Lombard (2)

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