Book Family Friendly Rentals in Chicago

We selected the best homes worth renting in this location

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Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

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Home spotlights

Chicago Chill Pad

Chicago Chill Pad

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Here awaits The Cooke, where guest security and solace are paramount. Ensconced in the heart of Chicago's distinguished Financial District, this property is a gateway to an array of unforgettable Windy City attractions.

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.

The Lion

The Lion

  • 5 guests

  • 2 bedrooms

Rush & Division, Chicago

This home is the perfect place to relax and enjoy your stay in Chicago. The home is located in the Gold Coast neighborhood, which is known for its luxury shops, fine dining, and lake Michigan charm.

All Things Glow

All Things Glow

  • 3 guests

  • 2 bedrooms

Hyde Park, Chicago

This apartment in Chicago's Hyde Park is positively flush with luxury touches. We love the trendy, timeless design, which merges mid-century pieces with a modern flair.


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

Explore the 4 most perfect homes in our collection

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Most popular homes

Chicago Chill Pad

Chicago Chill Pad

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Chicago Morning

Chicago Morning

  • 8 guests

  • 4 bedrooms

Printer's Row, Chicago

The Lion

The Lion

  • 5 guests

  • 2 bedrooms

Rush & Division, Chicago

All Things Glow

All Things Glow

  • 3 guests

  • 2 bedrooms

Hyde Park, Chicago

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Check upcoming rates & availability for Chicago Family Friendly Rentals


Frequently asked questions

Discover the ultimate collection of luxury Family Friendly Rentals in Chicago. 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 Chicago 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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