Book Luxury Holiday Rentals in Illinois

Award-winning homes from £98

Home spotlights in Illinois

Dusk in the City

Dusk in the City

  • 6 guests

  • 2 bedrooms

South Loop, Chicago

Show up and start living the Chicago city life at this sleek serviced apartment in the buzzy residential neighbourhood of South Loop. With its crowd-pleasing restaurants, vibrant soul and jazz clubs, and must-see sights – from the luxe mansions of Millionaires Row to Museum Campus – South Loop will not disappoint.

Drive Me Loopy

Drive Me Loopy

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

Whether you are staying for work or vacation, this high-rise apartment in trendy South Loop is perfectly located for all there is to eat, drink and do. Stepping in to look around at the chic decor, you'll notice how the cool industrial vibe is softened by the warm furniture, olive-green tones and wooden flooring.

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.

Hey Mr DJ

Hey Mr DJ

  • 6 guests

  • 2 bedrooms

South Loop, Chicago

Escape the hustle of downtown Chicago with a stay at this sleek serviced apartment in the buzzy neighbourhood of South Loop. Well-connected to downtown Boston (seventeen minutes by metro, or eight minutes in an Uber, to be precise), you can see why Chicagoans love to lay down roots here.


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

Explore the 42 most perfect homes in our collection

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Most popular homes in Illinois

Chocolate Mint

Chocolate Mint

  • 2 guests

  • 1 bedrooms

South Loop, Chicago

Lost in a Moment

Lost in a Moment

  • 6 guests

  • 3 bedrooms

Chicago Loop, Chicago

Loop In

Loop In

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

Diamonds Are Forever

Diamonds Are Forever

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

In Triplicate

In Triplicate

  • 8 guests

  • 3 bedrooms

Greektown, Chicago

Southern Loop

Southern Loop

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

Flaming Saganaki

Flaming Saganaki

  • 4 guests

  • 1 bedrooms

Greektown, Chicago

Let Yourself Go

Let Yourself Go

  • 4 guests

  • 1 bedrooms

South 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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