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: 388771
2bd, 2 full ba condo  in Rogers Park  - Vacation Rental in Chicago
From USD180 nt
2 Bedrooms
Sleeps 4
spectacular 2br/2ba top flr corner condo in rogers park. 9-unit gated complex. 12'ceilings, huge 24x23 liv rm w/custom built-in bookcase, fireplace and great natural light. brazilian cherry hdwd flrs ...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: 390662
exceptional vacational home - Vacation Rental in Chicago
 
4 Bedrooms
Sleeps 6
this is a beautiful and lovely home for vacation rental.....please contact... ...Read Full Description
ID: 114013
ASTER HOUSE Apartments of Lincoln Park - Vacation Rental in Chicago
 
4 Bedrooms
Sleeps 8
3 chicago self-catering flats / apartments! our apartments are in one of the finest locations possible, lincoln park. These self-catering fully furnished apartments are the perfect place to stay when ...Read Full Description
Inquire on multiple properties - Save time! Inquire, Compare offers, and Book.


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Sleeps: 3 Remove 3

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*Traveling Dates:

Flexible Dates
Bedrooms:
(vacation rentals only)
1 (2)
2 (1)
4+ (2)

Vacation Rental Types:
Apartment (4)
Home (1)

Lodging Types:
Hotels (1)

Location Attributes:
Lakefront (1)
Near water (1)
Near beach (3)
Waterfront (1)
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Amenities:
Sauna (2)
Coffee Maker (3)
Full Kitchen (3)
Air Conditioning (3)
Refrigerator (3)
TV/VCR (3)
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Things To Do:
Restaurants (3)
Museums (3)
Theaters / Cinemas (3)
Sightseeing (3)
Spa (1)
Swimming (3)
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Special Features:
Children Welcome (5)
Smoking Permitted (2)
Pet friendly (4)
Handicap accesibility (4)

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