Book Luxury Holiday Rentals in West Loop

Award-winning homes from £98

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Adults

Age 13+

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Children

Age 1 to 12

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Home spotlights in West Loop

Windy City Wonder

Windy City Wonder

  • 12 guests

  • 6 bedrooms

West Loop, Chicago

Planning a large group getaway to Chicago, but don’t want to get under each other’s toes? This trio of apartments in the same high-end serviced apartment complex should do the trick.

Chicago Chic

Chicago Chic

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

This pet-friendly apartment in Downtown Chicago puts the best of the city at your feet. Millennium Park, The Art Institute, theatres, restaurants, and shops are all just a short stroll away.

The Lion

The Lion

  • 5 guests

  • 2 bedrooms

Rush & Division, Chicago

This home is the perfect place to relax and enjoy your stay in Chicago. The home is located in the Gold Coast neighborhood, which is known for its luxury shops, fine dining, and lake Michigan charm.

The West-Loop Wavelength

The West-Loop Wavelength

  • 17 guests

  • 8 bedrooms

West Loop, Chicago

Welcome to a unique urban retreat, igniting the senses, and beckoning guests to indulge in the transformative charm of West Loop. Once an industrial essence, it has blossomed into a locus of gastronomy, nightlife, and style, dazzling visitors with its fusion of historic mortar and modern vibrance.


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

Explore the 44 most perfect homes in our collection

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Most popular homes in West Loop

Windy City Haven

Windy City Haven

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

Chicago Heights

Chicago Heights

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

Chicagoan Idyll

Chicagoan Idyll

  • 6 guests

  • 3 bedrooms

River West, Chicago

The Urban Villa

The Urban Villa

  • 6 guests

  • 2 bedrooms

Rush & Division, Chicago

Chicago Morning

Chicago Morning

  • 8 guests

  • 4 bedrooms

Printer's Row, Chicago

Chicago's Gemstone

Chicago's Gemstone

  • 7 guests

  • 3 bedrooms

Fulton River District, Chicago

Metropolis Retreat

Metropolis Retreat

  • 18 guests

  • 9 bedrooms

Fulton River District, Chicago

Charming Chicago Charm

Charming Chicago Charm

  • 5 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 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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