Book Family Friendly Rentals in Chicago Loop

We selected the 13 homes worth renting in this location

Home spotlights in Chicago Loop

Loop In

Loop In

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

Say hello to high-style city living at this sleek, serviced apartment in the heart of happening South Loop. Well-connected to downtown Boston, you’re never far from the Windy City action.

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.

New Millennium

New Millennium

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

The nineteenth-century architectural firm Adler & Sullivan was responsible for some of Chicago's most celebrated icons, including the city's Stock Exchange Building, the Auditorium Building and the Carrie Eliza Getty Tomb in Graceland Cemetery. They also designed the building in which this apartment sits in the area known locally as Jewelers Row.

The Jeweler's Gem

The Jeweler's Gem

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

Snug yet stylish, this studio apartment is perfect for a lone traveller or couple wanting a cosy stay in Chicago. We love the sleek design and jewel tones – fitting, seeing as this flat is situated along the famous Jewelers Row.


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

Explore the 13 most perfect homes in our collection

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Most popular homes in Chicago Loop

The Jeweller

The Jeweller

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

Lost in a Moment

Lost in a Moment

  • 6 guests

  • 3 bedrooms

Chicago Loop, Chicago

Running Loops

Running Loops

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

Monday Night

Monday Night

  • 3 guests

  • 1 bedrooms

South Loop, Chicago

I’m With The Band

I’m With The Band

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

Diamonds Are Forever

Diamonds Are Forever

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

Panorama Place

Panorama Place

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

Indigo Wabash

Indigo Wabash

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

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Frequently asked questions

Discover the ultimate collection of luxury Family Friendly Rentals in Chicago Loop, Chicago, 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 Chicago Loop 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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