Book Luxury Holiday Rentals in Cook County

Award-winning homes from £98

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Home spotlights in Cook County

Indigo Wabash

Indigo Wabash

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

A hidden gem among the towering skyscrapers and bustling streets, the building was designed by Adler & Sullivan and is surrounded by jewellers, some dating as far back as 1872. It's fair to say you've unearthed a diamond.

Diamonds Are Forever

Diamonds Are Forever

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

In an iconically Chicago building designed by Adler & Sullivan, this apartment sits amidst jewellery shops that have been trading since the 19th century and is just a couple of blocks from the sculpture-strewn Millennium Park. As well as old-world jewellery shops, contemporary galleries and trendy eateries fill the streets surrounding this apartment.

Southern Loop

Southern Loop

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

The living is easy at this smart apartment complex located right in the heart of buzzy South Loop, a popular residential area just south of downtown. Jam-packed with expansive green parks, prestigious museums, and legendary jazz clubs, it's easy to see why Chicagoans choose to lay down roots here.

Flaming Saganaki

Flaming Saganaki

  • 4 guests

  • 1 bedrooms

Greektown, Chicago

It's estimated that Chicago has the third-largest number of people with Greek ancestry out of any US city and nowhere is that seen more than in Greektown. In among the restaurants and museums dedicated to Hellenic culture, you'll find this great apartment.


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

Explore the 40 most perfect homes in our collection

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Most popular homes in Cook County

New Millennium

New Millennium

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

Hey Mr DJ

Hey Mr DJ

  • 6 guests

  • 2 bedrooms

South Loop, Chicago

Skyscraper

Skyscraper

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Easel And Brush

Easel And Brush

  • 5 guests

  • 2 bedrooms

Near North, Chicago

Panorama Place

Panorama Place

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

Drive Me Loopy

Drive Me Loopy

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

Chicago Morning

Chicago Morning

  • 8 guests

  • 4 bedrooms

Printer's Row, Chicago

The Jeweller

The Jeweller

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

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Explore our selection of the finest luxury Holiday Rentals for your next getaway in Cook County, Illinois, United States. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Cook County, Illinois, United States has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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