Cook County Romantic Accommodation

We selected the 22 homes worth renting in this location

Home spotlights in Cook County

Loop In

Loop In

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

Say hello to high-style city living at this sleek, serviced apartment in the heart of happening South Loop. Well-connected to downtown Boston, you’re never far from the Windy City action.

Running Loops

Running Loops

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

This stylish home-from-home is in Chicago’s artistic and culinary zeitgeist – South Loop. A cool and creative neighbourhood, known for its lively music scene, bold architecture and history, you’re within walking distance from the Museum Campus and Art Institute – perfect for city-breakers and culture vultures alike.

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.

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?


We selected the top 3% holiday homes in Cook County Romantic Accommodation

Explore the 22 most perfect homes in our collection

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Most popular homes in Cook County

Let Yourself Go

Let Yourself Go

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

Southern Loop

Southern Loop

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

Flaming Saganaki

Flaming Saganaki

  • 4 guests

  • 1 bedrooms

West Loop, Chicago

The Jeweler's Gem

The Jeweler's Gem

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

Bears In The Park

Bears In The Park

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

South Soul

South Soul

  • 2 guests

  • 1 bedrooms

South Loop, Chicago

Drive Me Loopy

Drive Me Loopy

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

The Jeweller

The Jeweller

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

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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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