Book Family Friendly Rentals in Cook County

We selected the 19 homes worth renting in this location

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Age 13+

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Age 1 to 12

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Home spotlights in Cook County

Windy City Haven

Windy City Haven

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

Welcome to a distinguished spot nestled in the vibrant pulse of the West Loop! All visitors are skillfully screened for safety and a damage hold is acquired prior to stay.

The Chi-town Charm

The Chi-town Charm

  • 3 guests

  • 2 bedrooms

West Loop, Chicago

Set in the heart of Chicago’s buzzing West Loop, this modern apartment is the perfect base for exploring the city. Step outside and you’re moments from acclaimed restaurants, vibrant markets and cultural landmarks – but when you’re not out and about, the building has plenty to keep you entertained.

The High Way

The High Way

  • 4 guests

  • 2 bedrooms

Rush & Division, Chicago

This smart city sanctuary boasts incredible views across the Chicago skyline. The rooms have been thoughtfully designed to inspire ease and relaxation.

Chicago Heights

Chicago Heights

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

This pet-friendly apartment in Downtown Chicago puts the city right at your feet, with Millennium Park, The Art Institute, theatres, and shopping just a stroll away. Inside, floor-to-ceiling windows in the main bedroom frame the skyline, while a sleek kitchen with a breakfast bar and a light-filled living space make staying in just as tempting as going out.


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

Explore the 19 most perfect homes in our collection

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Most popular homes in Cook County

Urban Vistas

Urban Vistas

  • 4 guests

  • 2 bedrooms

Rush & Division, Chicago

Chicago Chill Pad

Chicago Chill Pad

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Metropolis Retreat

Metropolis Retreat

  • 18 guests

  • 9 bedrooms

Fulton River District, Chicago

The West Wind Charm

The West Wind Charm

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

Chicagoan Idyll

Chicagoan Idyll

  • 6 guests

  • 3 bedrooms

River West, Chicago

WindyCity Wonders

WindyCity Wonders

  • 5 guests

  • 2 bedrooms

West Loop Gate, Chicago

The Lofted Escape

The Lofted Escape

  • 7 guests

  • 3 bedrooms

Fulton River District, Chicago

Chicago Morning

Chicago Morning

  • 8 guests

  • 4 bedrooms

Printer's Row, Chicago

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Check upcoming rates & availability for Cook County Family Friendly Rentals


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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