Book Luxury Holiday Rentals in Illinois

Award-winning homes from £98

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Home spotlights in Illinois

All Things Glow

All Things Glow

  • 3 guests

  • 2 bedrooms

Hyde Park, Chicago

This apartment in Chicago's Hyde Park is positively flush with luxury touches. We love the trendy, timeless design, which merges mid-century pieces with a modern flair.

The Jeweller

The Jeweller

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

Just a block away from Millennium Park and the Art Institute of Chicago, this neat little apartment puts you in the centre of the Windy City. It’s a three-minute walk to Millennium Park where you’ll find fountains, playparks and sculptures, including the iconic Bean.

Flaming Saganaki

Flaming Saganaki

  • 4 guests

  • 1 bedrooms

Greektown, Chicago

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.

Southern Loop

Southern Loop

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

The living is easy at this smart apartment complex located right in the heart of buzzy South Loop, a popular residential area just south of downtown. Jam-packed with expansive green parks, prestigious museums, and legendary jazz clubs, it's easy to see why Chicagoans choose to lay down roots here.


We selected the top 3% holiday homes in Illinois Holiday Rentals

Explore the 41 most perfect homes in our collection

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Most popular homes in Illinois

In Triplicate

In Triplicate

  • 8 guests

  • 3 bedrooms

Greektown, Chicago

South Soul

South Soul

  • 2 guests

  • 1 bedrooms

South Loop, Chicago

Bears In The Park

Bears In The Park

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

The Jeweler's Gem

The Jeweler's Gem

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

Let Yourself Go

Let Yourself Go

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

Chocolate Mint

Chocolate Mint

  • 2 guests

  • 1 bedrooms

South Loop, Chicago

Drive Me Loopy

Drive Me Loopy

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

Indigo Wabash

Indigo Wabash

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in 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 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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