Cook County Romantic Accommodation

We selected the 36 homes worth renting in this location

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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

The Chi-town Charm

The Chi-town Charm

  • 3 guests

  • 2 bedrooms

West Loop, Chicago

Set in the heart of Chicago’s buzzing West Loop, this modern apartment is the perfect base for exploring the city. Step outside and you’re moments from acclaimed restaurants, vibrant markets and cultural landmarks – but when you’re not out and about, the building has plenty to keep you entertained.

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.

Urban Vistas

Urban Vistas

  • 4 guests

  • 2 bedrooms

Rush & Division, Chicago

This Illinois apartment won us over the moment we clapped eyes on the sweeping views of Chicago’s skyline and that private balcony. But the perks don’t end there.

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 Romantic Accommodation

Explore the 36 most perfect homes in our collection

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Most popular homes in Cook County

Chicago Charisma

Chicago Charisma

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Westside Retreat

Westside Retreat

  • 7 guests

  • 3 bedrooms

River West, Chicago

Chicago Chill Pad

Chicago Chill Pad

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Chicago Heights

Chicago Heights

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

WindyCity Wonders

WindyCity Wonders

  • 5 guests

  • 2 bedrooms

West Loop Gate, Chicago

Loop Haven

Loop Haven

  • 12 guests

  • 6 bedrooms

Chicago Loop, Chicago

Charming Chicago Charm

Charming Chicago Charm

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Chicagoan Idyll

Chicagoan Idyll

  • 6 guests

  • 3 bedrooms

River West, Chicago

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Check upcoming rates & availability for Cook County Romantic Accommodation


Frequently asked questions

Discover the most romantic accommodation in Cook County, Illinois, United States. We’ve handpicked homes that are perfect for two, in soulful neighbourhood locations with characterful living spaces, sumptuous bedrooms and luxurious bathrooms. Book today and enjoy a short or extended stay in the most romantic accommodation that Cook County, Illinois, United States has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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