Book Luxury Vacation Rentals in Chicago

Award-winning homes from £98

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Home spotlights in Chicago

Flaming Saganaki

Flaming Saganaki

  • 4 guests

  • 1 bedrooms

Greektown, Chicago

It's estimated that Chicago has the third-largest number of people with Greek ancestry out of any US city and nowhere is that seen more than in Greektown. In among the restaurants and museums dedicated to Hellenic culture, you'll find this great apartment.

Southern Loop

Southern Loop

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

The living is easy at this smart apartment complex located right in the heart of buzzy South Loop, a popular residential area just south of downtown. Jam-packed with expansive green parks, prestigious museums, and legendary jazz clubs, it's easy to see why Chicagoans choose to lay down roots here.

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.


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

Explore the 40 most perfect homes in our collection

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Most popular homes in Chicago

New Millennium

New Millennium

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

Hey Mr DJ

Hey Mr DJ

  • 6 guests

  • 2 bedrooms

South Loop, Chicago

Easel And Brush

Easel And Brush

  • 5 guests

  • 2 bedrooms

Near North, Chicago

The Jeweler's Gem

The Jeweler's Gem

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

Monday Night

Monday Night

  • 3 guests

  • 1 bedrooms

South Loop, Chicago

Bears In The Park

Bears In The Park

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

Panorama Place

Panorama Place

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

The Jeweller

The Jeweller

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

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Frequently asked questions

Take a look at our collection of luxury Vacation Rentals in 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 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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