Book Luxury Holiday Rentals in West Loop

Award-winning homes from £98

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Home spotlights in West Loop

Checking Account

Checking Account

  • 2 guests

  • 1 bedrooms

Near North, Chicago

Get out your Chicago apartment checklist and be prepared to get ticking as this apartment has all you need for your time in the Windy City. You'll find fantastic views through the floor-to-ceiling windows, ideal for admiring while you work at the desk or lounge on the sofa.

Panorama Place

Panorama Place

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

Chicago is laid out at your feet thanks to the floor-to-ceiling windows of this home. Whether you're watching TV in the white living space, cooking up a feast in the pine kitchen or waking up on the memory foam mattresses in the bedrooms, the skyline is visible.

Gilded Frame

Gilded Frame

  • 3 guests

  • 1 bedrooms

Near North, Chicago

If you’re an art lover looking to visit Chicago, then you’ve come to the right place. River North, where this delightful one-bedroom is located, has the highest concentration of galleries in the US, after Manhattan.

Slice Of Sky

Slice Of Sky

  • 3 guests

  • 1 bedrooms

Rush & Division, Chicago

Surrounded by skyline and soaring scrapers, this city apartment boasts a central Chicago location that sets you up for an instant retreat. With artwork and windows out onto River North for decoration, this home’s style could not be more fitting of its urban exterior.


We selected the top 3% holiday homes in West Loop Holiday Rentals

Explore the 46 most perfect homes in our collection

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Most popular homes in West Loop

Savings Account

Savings Account

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Monday Night

Monday Night

  • 3 guests

  • 1 bedrooms

South Loop, Chicago

Easel And Brush

Easel And Brush

  • 5 guests

  • 2 bedrooms

Near North, Chicago

On Cloud Nine

On Cloud Nine

  • 2 guests

  • 1 bedrooms

Near North, Chicago

Chicago Morning

Chicago Morning

  • 8 guests

  • 4 bedrooms

Printer's Row, Chicago

Work & Play

Work & Play

  • 2 guests

  • 1 bedrooms

Near North, Chicago

Solo Bird

Solo Bird

  • 2 guests

  • 1 bedrooms

Near North, Chicago

Grey Marl

Grey Marl

  • 3 guests

  • 1 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 West Loop. 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 West Loop 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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