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: 383963
ONE FURNISHED BEDROOM FOR RENT IN CENTER CHICAGO A - Vacation Rental in Chicago
 
2 Bedrooms
Sleeps 1
utilities: kitchen,washing machine,american kitchen fridge & freezer oven,microwave dish washer crockery & utensils,bath shower hair dryer,towels extra features internet dial up, internet bro ...Read Full Description
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 Studio Apartment - Vacation Rental in Chicago
 
Studio
Sleeps 2
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
Presidential Towers Luxury Studio - Vacation Rental in Chicago
From USD163 nt
Studio
Sleeps 2
31 night minimum stay; this high-end unit has granite countertops, stainless steel appliances, washer/dryer in-unit, a king bed, and a flat screen tv. Enjoy all-inclusive pricing and automatic monthly ...Read Full Description
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: 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: 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: 64648
The Westin Michigan Avenue Chicago - Hotel in Chicago
 
751 Bedrooms
Location. The westin michigan avenue chicago stands amid michigan avenue's shopping corridor in chicago, ill. the john hancock center is located across the street, and water tower place shops are posi ...Read Full Description
ID: 64648
Hotel Allegro Chicago - A Kimpton Hotel - Hotel in Chicago
 
483 Bedrooms
Location. The hotel allegro chicago is located in the loop's theater and business district in chicago, ill. this property stands adjacent to the cadillac palace theatre, while magnificent mile shops a ...Read Full Description
ID: 64648
Avenue Hotel Chicago - Hotel in Chicago
 
350 Bedrooms
Location. The avenue hotel chicago is located one-half block from michigan avenue shops in chicago, ill. the hotel is three blocks from lake michigan and four blocks from water tower place. the sears ...Read Full Description
ID: 64648
PARK HYATT CHICAGO - Hotel in Chicago
 
198 Bedrooms
-property description
flagship of the park hyatt brand, offering a unique
alternative to your travelers current 5 star options. State
of the art guest rooms featuring dvd/cd pl ...Read Full Description
ID: 64648
The Whitehall Hotel - Hotel in Chicago
 
221 Bedrooms
Location. Central to the gold coast neighborhood in chicago, ill., the whitehall hotel radiates european style. the hotel is less than two blocks from rush street restaurants and nightclubs, and north ...Read Full Description
ID: 64648
Best Western River North Hotel - Hotel in Chicago
 
150 Bedrooms
Location. <ul><li> the best western river north hotel is located in chicago, ill.</li> <li>five blocks from north michigan avenue</li& ...Read Full Description
Inquire on multiple properties - Save time! Inquire, Compare offers, and Book.


Smart Search


Sleeps: 1 Remove 1

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*Traveling Dates:

Flexible Dates
Bedrooms:
(vacation rentals only)
Studio (2)
1 (4)
2 (2)
4+ (64)

Vacation Rental Types:
Apartment (6)
Home (2)

Lodging Types:
Hotels (68)
Vacation Rentals (8)

Location Attributes:
Lakefront (2)
Near beach (4)
Waterfront (1)
Beachfront (1)
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Amenities:
Sauna (20)
Coffee Maker (12)
Full Kitchen (11)
Air Conditioning (9)
Refrigerator (6)
TV/VCR (7)
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Things To Do:
Restaurants (6)
Museums (5)
Theaters / Cinemas (5)
Sightseeing (6)
Spa (2)
Swimming (4)
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Special Features:
Children Welcome (76)
Smoking Permitted (71)
Pet friendly (75)
Handicap accesibility (64)

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Note: Use Search Destination box (above) to browse listings in these vicinities.
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 (5)
Burr Ridge (1)
Willowbrook (4)
Oakbrook (2)
Oakbrook Terrace (3)
Des Plaines (7)
South Holland (2)
Westmont (3)
Addison (3)
Lombard (6)
Orland Park (1)

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