Book Luxury Vacation Rentals in Chicago Loop

Award-winning homes from £98

Home spotlights in Chicago Loop

Diamonds Are Forever

Diamonds Are Forever

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

In an iconically Chicago building designed by Adler & Sullivan, this apartment sits amidst jewellery shops that have been trading since the 19th century and is just a couple of blocks from the sculpture-strewn Millennium Park. As well as old-world jewellery shops, contemporary galleries and trendy eateries fill the streets surrounding this apartment.

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.

Windy City Retreat

Windy City Retreat

  • 20 guests

  • 10 bedrooms

Chicago Loop, Chicago

Welcome to a piece of paradise nestled serenely in Chicago's vibrant heartbeat, the Financial District. Immerse yourself in an ambiance that elegantly melds grandeur and finesse while simultaneously providing cobblestone-quiet comfort amid city hustle.

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.


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

Explore the 21 most perfect homes in our collection

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Most popular homes in Chicago Loop

New Millennium

New Millennium

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

The Treasury

The Treasury

  • 5 guests

  • 2 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

Loop Luxe

Loop Luxe

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Down South Again

Down South Again

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Running Loops

Running Loops

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

Loop Haven

Loop Haven

  • 12 guests

  • 6 bedrooms

Chicago Loop, Chicago

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Frequently asked questions

Take a look at our collection of luxury Vacation Rentals in Chicago Loop, Chicago, Cook County, Illinois, United States. All of the homes you'll find on Plum Guide come fully furnished with all linen, the best-equipped kitchens, and essential bathroom toiletries included. Each home is systematically reviewed before becoming part of our collection, so you can book your stay with total confidence. And if you require any assistance in finding the perfect Chicago Loop Vacation Rentals for you, get in touch with our team of friendly experts, on hand to help with whatever you need.

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