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.

Modern Dream

Modern Dream

  • 3 guests

  • 1 bedrooms

Near North, Chicago

This bright and breezy apartment is perfect for a couple looking for a change of scenery. The space is set up perfectly for the travelling professional – with plenty of desk space and fast wi-fi to work from home.

Bluegill

Bluegill

  • 3 guests

  • 1 bedrooms

Near North, Chicago

This home in Chicago's chic River North neighbourhood is set just three blocks from the Magnificent Mile and six from the Museum of Contemporary Art. Design lovers and art aficionados will appreciate the number of galleries within walking distance, while foodies will be just as excited to eat their way through the fantastic gastronomic scene.

Skyscraper

Skyscraper

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Arriving at this home in downtown Chicago, you’re sure to be charmed by the typically Chicagoan high rise. Gaze down on the city above, and delight in the central location in the North River district – it's famous for its abundance of galleries and arty culture.


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

Explore the 24 most perfect homes in our collection

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Most popular homes in Illinois

Grey Marl

Grey Marl

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Work & Play

Work & Play

  • 2 guests

  • 1 bedrooms

Near North, Chicago

Solo Breeze

Solo Breeze

  • 2 guests

  • 1 bedrooms

Near North, Chicago

Monday Night

Monday Night

  • 3 guests

  • 1 bedrooms

South Loop, Chicago

Slice Of Sky

Slice Of Sky

  • 3 guests

  • 1 bedrooms

Rush & Division, Chicago

I’m With The Band

I’m With The Band

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

Panorama Place

Panorama Place

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

Easel And Brush

Easel And Brush

  • 5 guests

  • 2 bedrooms

Near North, 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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