Chicago Holiday Homes with Childcare

We selected the 23 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

0

Pets

An extra fee may apply

0

Home spotlights in Chicago

Panorama Place

Panorama Place

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

Chicago is laid out at your feet thanks to the floor-to-ceiling windows of this home. Whether you're watching TV in the white living space, cooking up a feast in the pine kitchen or waking up on the memory foam mattresses in the bedrooms, the skyline is visible.

Checking Account

Checking Account

  • 2 guests

  • 1 bedrooms

Near North, Chicago

Get out your Chicago apartment checklist and be prepared to get ticking as this apartment has all you need for your time in the Windy City. You'll find fantastic views through the floor-to-ceiling windows, ideal for admiring while you work at the desk or lounge on the sofa.

Monday Night

Monday Night

  • 3 guests

  • 1 bedrooms

South Loop, Chicago

Convenience is key at this stylish apartment in Chicago’s trendy River North neighbourhood. From the moment you wake up in your plush, king-size bed you'll take in sprawling city views from the floor-to-ceiling windows.

Slice Of Sky

Slice Of Sky

  • 3 guests

  • 1 bedrooms

Rush & Division, Chicago

Surrounded by skyline and soaring scrapers, this city apartment boasts a central Chicago location that sets you up for an instant retreat. With artwork and windows out onto River North for decoration, this home’s style could not be more fitting of its urban exterior.


We selected the top 3% holiday homes in Chicago Holiday Homes with Childcare

Explore the 23 most perfect homes in our collection

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Most popular homes in Chicago

Gilded Frame

Gilded Frame

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Easel And Brush

Easel And Brush

  • 5 guests

  • 2 bedrooms

Near North, Chicago

Savings Account

Savings Account

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Chicago Morning

Chicago Morning

  • 8 guests

  • 4 bedrooms

Printer's Row, Chicago

Bluegill

Bluegill

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Modern Dream

Modern Dream

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Solo Bird

Solo Bird

  • 2 guests

  • 1 bedrooms

Near North, Chicago

Skyscraper

Skyscraper

  • 3 guests

  • 1 bedrooms

Near North, Chicago

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Check upcoming rates & availability for Chicago Holiday Homes with Childcare


Frequently asked questions

Looking for holiday homes with childcare in Chicago, Cook County, Illinois, United States? You’ve come to the right place: speak to one of our Plum Experts who can arrange childcare as an addition to your booking in Chicago, Cook County, Illinois, United States. Enjoy your trip away, comfortable in the knowledge that the kids are being looked after. All of our Plum Guide rentals are fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Our experts are on hand day and night to help if you ever need anything.

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