Book a stay in one of the best homes in Chicago

We selected the 23 homes worth renting in this location

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Adults

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Age 1 to 12

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Home spotlights in Chicago

Easel And Brush

Easel And Brush

  • 5 guests

  • 2 bedrooms

Near North, Chicago

If you’re visiting Chicago and you're interested in art, then the chic River North neighbourhood is the perfect place to stay. The area is now the city’s art and design quarter, with the highest concentration of galleries in the US after Manhattan.

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.

On Cloud Nine

On Cloud Nine

  • 2 guests

  • 1 bedrooms

Near North, Chicago

Chicago isn't just known for its lively music scene and deep-dish pizza, but also for its larger-than-life architecture – after all, those skyscrapers speak for themselves. The best way to make the most of the magnificent metropolis?

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.


We selected the top 3% holiday homes in Chicago

Explore the 23 most perfect homes in our collection

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Most popular homes in Chicago

Checking Account

Checking Account

  • 2 guests

  • 1 bedrooms

Near North, Chicago

Gilded Frame

Gilded Frame

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Monday Night

Monday Night

  • 3 guests

  • 1 bedrooms

South Loop, Chicago

Savings Account

Savings Account

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Skyscraper

Skyscraper

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Solo Bird

Solo Bird

  • 2 guests

  • 1 bedrooms

Near North, Chicago

I’m With The Band

I’m With The Band

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

Modern Dream

Modern Dream

  • 3 guests

  • 1 bedrooms

Near North, Chicago

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