Book Luxury Vacation Rentals in Cook County

Award-winning homes from £98

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Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

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Home spotlights in Cook County

Chicago Sanctuary

Chicago Sanctuary

  • 5 guests

  • 2 bedrooms

Rush & Division, Chicago

Welcome to The Gold Coast Gem! This luxurious retreat in Chicago's prestigious Gold Coast neighborhood offers an elegant and tranquil escape.

Windy City Haven

Windy City Haven

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

Welcome to a distinguished spot nestled in the vibrant pulse of the West Loop! All visitors are skillfully screened for safety and a damage hold is acquired prior to stay.

The Chi-town Charm

The Chi-town Charm

  • 3 guests

  • 1 bedrooms

West Loop, Chicago

Step into The Wilco, located in the lively West Loop area. This charming nest brings you closer to an otherworldly dining and entertainment epoch that has truly transformed its past industry-led persona.

Metropolis Retreat

Metropolis Retreat

  • 18 guests

  • 9 bedrooms

Fulton River District, Chicago

Welcome to The Bean! The perfect urban escape awaits you in this contemporary style gem.


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

Explore the 40 most perfect homes in our collection

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Most popular homes in Cook County

Loop Haven

Loop Haven

  • 12 guests

  • 6 bedrooms

Chicago Loop, Chicago

The West Wind Charm

The West Wind Charm

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

WindyCity Wonders

WindyCity Wonders

  • 6 guests

  • 2 bedrooms

West Loop Gate, Chicago

Chicago Chill Pad

Chicago Chill Pad

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Wicked Windy Retreat

Wicked Windy Retreat

  • 6 guests

  • 2 bedrooms

Rush & Division, Chicago

Elevated Luxe

Elevated Luxe

  • 5 guests

  • 2 bedrooms

Fulton River District, Chicago

The West-Loop Wavelength

The West-Loop Wavelength

  • 17 guests

  • 8 bedrooms

West Loop, Chicago

Charm of Chicago

Charm of Chicago

  • 5 guests

  • 2 bedrooms

Rush & Division, Chicago

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Frequently asked questions

Similar destinations

Take a look at our collection of luxury Vacation Rentals in Cook County, Illinois, United States. All of the homes you'll find on Plum Guide come fully furnished with all linen, the best-equipped kitchens, and essential bathroom toiletries included. Each home is systematically reviewed before becoming part of our collection, so you can book your stay with total confidence. And if you require any assistance in finding the perfect Cook County Vacation Rentals for you, get in touch with our team of friendly experts, on hand to help with whatever you need.

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