Cook County Romantic Accommodation

We selected the 21 homes worth renting in this location

Home spotlights in Cook County

On Cloud Nine

On Cloud Nine

Near North, Chicago

  • 2 guests

  • 1 bedrooms

£382 night

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?

Diamonds Are Forever

Diamonds Are Forever

Chicago Loop, Chicago

  • 2 guests

  • 1 bedrooms

£386 night

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.

Flaming Saganaki

Flaming Saganaki

Greektown, Chicago

  • 4 guests

  • 1 bedrooms

£474 night

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 Romantic Accommodation

Explore the 21 most perfect homes in our collection

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Most popular homes in Cook County

The Jeweler's Gem

The Jeweler's Gem

Chicago Loop, Chicago

  • 2 guests

  • 1 bedrooms

£371 night

Southern Loop

Southern Loop

South Loop, Chicago

  • 4 guests

  • 1 bedrooms

£441 night

South Soul

South Soul

South Loop, Chicago

  • 2 guests

  • 1 bedrooms

£327 night

Drive Me Loopy

Drive Me Loopy

South Loop, Chicago

  • 4 guests

  • 1 bedrooms

£533 night

The Jeweller

The Jeweller

Chicago Loop, Chicago

  • 2 guests

  • 1 bedrooms

£413 night

Let Yourself Go

Let Yourself Go

South Loop, Chicago

  • 4 guests

  • 1 bedrooms

£437 night

Savings Account

Savings Account

Near North, Chicago

  • 3 guests

  • 1 bedrooms

£441 night

Bears In The Park

Bears In The Park

South Loop, Chicago

  • 4 guests

  • 1 bedrooms

£410 night

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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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