Book Family Friendly Rentals in Cook County

We selected the 41 homes worth renting in this location

Home spotlights in Cook County

Lost in a Moment

Lost in a Moment

  • 6 guests

  • 3 bedrooms

Chicago Loop, Chicago

This pad right in Chicago's South Loop puts the city at your fingertips. While foodies chow down at the many delicious restaurants on your doorstep, culture vultures can spend the afternoon roaming around the famous Field Museum and other nearby galleries.

The Jeweller

The Jeweller

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

Just a block away from Millennium Park and the Art Institute of Chicago, this neat little apartment puts you in the centre of the Windy City. It’s a three-minute walk to Millennium Park where you’ll find fountains, playparks and sculptures, including the iconic Bean.

Chicago Morning

Chicago Morning

  • 8 guests

  • 4 bedrooms

Printer's Row, Chicago

Initially designed by an architect for their family, this incredible Chicago condo has been featured in magazines and even TV commercials. Located in the heart of downtown Chicago, this home is central to the sights and activities of the area, and also boasts an incredible green, real grass rooftop terrace with views that span across the south, east, and west of the city.

Hey Mr DJ

Hey Mr DJ

  • 6 guests

  • 2 bedrooms

South Loop, Chicago

Escape the hustle of downtown Chicago with a stay at this sleek serviced apartment in the buzzy neighbourhood of South Loop. Well-connected to downtown Boston (seventeen minutes by metro, or eight minutes in an Uber, to be precise), you can see why Chicagoans love to lay down roots here.


We selected the top 3% holiday homes in Cook County Family Friendly Rentals

Explore the 41 most perfect homes in our collection

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Most popular homes in Cook County

New Millennium

New Millennium

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

Southern Loop

Southern Loop

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

Drive Me Loopy

Drive Me Loopy

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

In Triplicate

In Triplicate

  • 8 guests

  • 3 bedrooms

Greektown, Chicago

Flaming Saganaki

Flaming Saganaki

  • 4 guests

  • 1 bedrooms

Greektown, Chicago

Designed For Life

Designed For Life

  • 5 guests

  • 2 bedrooms

Near North, Chicago

Bluegill

Bluegill

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Let Yourself Go

Let Yourself Go

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

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Frequently asked questions

Discover the ultimate collection of luxury Family Friendly Rentals in Cook County, Illinois, United States. Here at Plum Guide, we prioritise customer satisfaction over everything, which is why we are so meticulous in what we do. Every home in our collection has been put through a vigorous 150-step vetting process, so we promise consistent quality you can count on. Each rental also comes fully furnished will essential bathroom toiletries, an excellently-equipped kitchen, and all linen included. Rent Cook County Family Friendly Homes now and secure yourself a trip to remember for all the right reasons. And call on the help of our friendly team, on standby night and day to ensure that your decision process is made as straightforward as possible.

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