Chicagoland Vacation Rentals

31 Chicagoland Rentals

List Map

Studio / 1BA - Sleeps 2 - Chicago Apartment

Corporate furnished apartment in the heart of Millennium Park, walking distance to transportation,...

$99 - $149 / nt

Chicago Illinois Vacation Rentals - Condo

5BR / 2BA - Sleeps 16 - Chicago Condo

Chicago Vacation Rental lenience # 2320200 This well kept property sleeps 14 comfortably with space...

$600 - $1,200 / nt

3 Reviews

1BR / 1BA - Sleeps 3 - Chicago Apartment

These Vacation Rentals are located in the Chicago LOOP, a mixed- use neighborhood west of Michigan Avenue...

$89 - $220 / nt

5 Reviews

4BR / 4BA - Sleeps 14 - Chicago Condo

A total of 4 bedroom 4 bath brand new construction luxury condos. We are a licensed vacation rental property...

$295 - $695 / nt

3BR / 2BA - Sleeps 8 - Chicago Townhouse

Gorgeous, Luxury Oak Park area Townhome…corner unit…completely furnished…. close proximity (2...

$300 - $450 / nt

Chicago Illinois Vacation Rentals - Condo

1BR / 1BA - Sleeps 4 - Chicago Condo

Experience the vibrancy of down town Chicago and delight in the modern, sleek comfort of wyndham grand...

$270 - $340 / nt

Chicago Illinois Vacation Rentals - Condo

3BR / 1BA - Sleeps 7 - Chicago Condo

Features 2 "independent" self catering units in the same building with fully functional kitchens. Coffee,...

$210 - $250 / nt

7 Reviews
Chicago Illinois Vacation Rentals - Apartment

1BR / 1BA - Sleeps 3 - Chicago Apartment

Located in the heart of Chicago, these Corporate Furnished Apartments offer breathtaking views, rooftop...

$100 - $180 / nt

8 Reviews
Chicago Illinois Vacation Rentals - Condo

10BR / 8BA - Sleeps 20 - Chicago Condo

Independent Bedroom Close to Downtown Chicago 18th dorm is located on heart of Pilsen. the six corner...

$50 - $60 / nt

Chicago Illinois Vacation Rentals - Condo

3BR / 2BA - Sleeps 6 - Chicago Condo

Beautifully done high- end furnished 2BR, 2BA in Old Town w/12ft ceilings, hardwood flrs, chef's kitchen...

$100 / nt

Chicago Illinois Vacation Rentals - Condo

1BR / 1BA - Sleeps 4 - Chicago Condo

If you're looking for a quiet and quaint stay in Chicago that is minutes away from all of the downtown...

$115 - $200 / nt

10 Reviews
Chicago Illinois Vacation Rentals - Condo

2BR / 2BA - Sleeps 4 - Chicago Condo

, overlooking city, Lake Michigan and the Chicago River. Fully furnished 2 bedroom/2 bath. Building...

10 Reviews
Chicago Illinois Vacation Rentals - Condo

4BR / 2BA - Sleeps 8 - Chicago Condo

Brand new 4 bedroom 2 bath fully furnished apartment in the heart of Roscoe Village. Whether you’re...

2 Reviews
Chicago vacation rentals are a great bet for those of you looking to plan something extra special this holiday season. Stunning view of the beaches, easy access to the waterfront, and perfect positioning to reach any shopping destination or restaurant with ease, are some of the benefits you enjoy while staying Chicago.

Most of the condos of Chicago offer great city views, in addition to having facilities like fully equipped kitchens, the latest electronic equipment, high-speed internet, and well-designed interiors.

The windy city, as it is popularly known, is best enjoyed on a cruise boat ride. Chicago boasts of some of the best skyscrapers in the world. Moving along the Chicago River, you come across two of the biggest architectural marvels – the Willis tower and the Tribune Tower.

Most of the Chicago vacation rentals have accessibility to Lake Michigan, which is another feather in Chicago’s cap. Taking a speedboat ride in Lake Michigan and experiencing a view of the Chicago skyline is sure to leave you and your family spellbound. Other spots to be enjoyed while in Chicago include the Chicago harbor, Grant Park, Buckingham fountain, and Museum campus.

The Buckingham fountain is best enjoyed after dusk, ideally around 8 ‘o’ clock in the evening. Commissioned by Kate Buckingham in 1927, this massive fountain has about 134 jets which ensure that the water rises to heights comfortably exceeding 24 feet., and with music and animation it really adds to the appeal.

A trip to Chicago would be incomplete without a visit to Hancock tower. From one of Chicago’s tallest landmarks, one can easily spot 4 states – Michigan, Illinois, Indiana, and Wisconsin. When experiencing the open-air sky deck, at least 1000 feet above the Magnificent Mile, with the wind on your face, you understand what makes people call Chicago as the ‘Windy City’.

Navy pier, parks, world famous restaurants, and museums – the list seems to be endless. Book your Chicago vacation rentals and it will just be a matter of time before your family members say ‘Go-Chicago’.
Click for larger map
Show big map »
  • Availability

  • Price

  • Bedrooms


  • Amenities

    • Show More...