Book Luxury Short Stay Rentals in Chicago Loop

We selected the 21 homes worth renting in this location

Home spotlights in Chicago Loop

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.

Lost in a Moment

Lost in a Moment

  • 6 guests

  • 3 bedrooms

Chicago Loop, Chicago

This pad right in Chicago's South Loop puts the city at your fingertips. While foodies chow down at the many delicious restaurants on your doorstep, culture vultures can spend the afternoon roaming around the famous Field Museum and other nearby galleries.

Loop In

Loop In

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

Say hello to high-style city living at this sleek, serviced apartment in the heart of happening South Loop. Well-connected to downtown Boston, you’re never far from the Windy City action.

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.


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

Explore the 21 most perfect homes in our collection

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Most popular homes in Chicago Loop

Diamonds Are Forever

Diamonds Are Forever

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

Windy City Retreat

Windy City Retreat

  • 20 guests

  • 10 bedrooms

Chicago Loop, Chicago

Chicago Morning

Chicago Morning

  • 8 guests

  • 4 bedrooms

Printer's Row, Chicago

The Jeweller

The Jeweller

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

Chicago Charisma

Chicago Charisma

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

The Treasury

The Treasury

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Monday Night

Monday Night

  • 3 guests

  • 1 bedrooms

South Loop, Chicago

I’m With The Band

I’m With The Band

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

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Frequently asked questions

Browse our curated collection of Short Stay Rentals in Chicago Loop, Chicago, Cook County, Illinois, United States. From impeccable interior design and chef-worthy kitchens, to fully furnished bathrooms and the inclusion of all linens, the homes in our collection come complete with everything you need. Each of the Chicago Loop luxury short stay apartments in our collection has been expertly reviewed to ensure the quality standards you can trust, so book today to enjoy a getaway to remember. And should you need any assistance, our friendly team of experts are here to help you find the perfect home.

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