Book Luxury Holiday Rentals in Cook County

Award-winning homes from £98

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Adults

Age 13+

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Age 1 to 12

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Home spotlights in Cook County

The Chicago River Rhapsody

The Chicago River Rhapsody

  • 14 guests

  • 6 bedrooms

River West, Chicago

Picture yourself unwinding amidst the spirited charm of River West in The Kane. The vivacious neighborhood edges the restful waves of the Chicago River, its boulevard bustling with inviting eateries, captivating bars, and eclectic boutiques.

Windy City Wonder

Windy City Wonder

  • 12 guests

  • 6 bedrooms

West Loop, Chicago

Planning a large group getaway to Chicago, but don’t want to get under each other’s toes? This trio of apartments in the same high-end serviced apartment complex should do the trick.

Skyline Reverie

Skyline Reverie

  • 7 guests

  • 3 bedrooms

River West, Chicago

High above River West, this spectacular home with skyline views invites you to experience Chicago at its most inspiring. Floor-to-ceiling windows keep the city close at every moment, while the balcony gives you a private stage for sunrise coffees and evening cocktails under glittering lights.

The High Way

The High Way

  • 4 guests

  • 2 bedrooms

Rush & Division, Chicago

This smart city sanctuary boasts incredible views across the Chicago skyline. The rooms have been thoughtfully designed to inspire ease and relaxation.


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

Explore the 36 most perfect homes in our collection

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Most popular homes in Cook County

Chicago Heights

Chicago Heights

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

Westside Retreat

Westside Retreat

  • 7 guests

  • 3 bedrooms

River West, Chicago

WindyCity Wonders

WindyCity Wonders

  • 5 guests

  • 2 bedrooms

West Loop Gate, Chicago

Metropolis Respite

Metropolis Respite

  • 7 guests

  • 3 bedrooms

Fulton River District, Chicago

Chicago Vista

Chicago Vista

  • 6 guests

  • 2 bedrooms

Rush & Division, Chicago

The West-Loop Wavelength

The West-Loop Wavelength

  • 17 guests

  • 8 bedrooms

West Loop, Chicago

Windy City Haven

Windy City Haven

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

Chicago's Gemstone

Chicago's Gemstone

  • 7 guests

  • 3 bedrooms

Fulton River District, Chicago

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Frequently asked questions

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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