Book Luxury Holiday Rentals in Chicago Loop

Award-winning homes from £98

Home spotlights in Chicago Loop

The Jeweler's Gem

The Jeweler's Gem

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

Snug yet stylish, this studio apartment is perfect for a lone traveller or couple wanting a cosy stay in Chicago. We love the sleek design and jewel tones – fitting, seeing as this flat is situated along the famous Jewelers Row.

New Millennium

New Millennium

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

The nineteenth-century architectural firm Adler & Sullivan was responsible for some of Chicago's most celebrated icons, including the city's Stock Exchange Building, the Auditorium Building and the Carrie Eliza Getty Tomb in Graceland Cemetery. They also designed the building in which this apartment sits in the area known locally as Jewelers Row.

Indigo Wabash

Indigo Wabash

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

A hidden gem among the towering skyscrapers and bustling streets, the building was designed by Adler & Sullivan and is surrounded by jewellers, some dating as far back as 1872. It's fair to say you've unearthed a diamond.

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.


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

Explore the 21 most perfect homes in our collection

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Most popular homes in Chicago Loop

Chicago Morning

Chicago Morning

  • 8 guests

  • 4 bedrooms

Printer's Row, Chicago

Diamonds Are Forever

Diamonds Are Forever

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

Loop Luxe

Loop Luxe

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Loop In

Loop In

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

The Treasury

The Treasury

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Chicago Chill Pad

Chicago Chill Pad

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Loop Haven

Loop Haven

  • 12 guests

  • 6 bedrooms

Chicago Loop, Chicago

Windy City Retreat

Windy City Retreat

  • 20 guests

  • 10 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 Chicago Loop, Chicago, Cook County, 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 Chicago Loop, Chicago, Cook County, 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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