Book a stay in one of the best homes in Chicago

We selected the 39 homes worth renting in this location

Home spotlights in Chicago

Running Loops

Running Loops

South Loop, Chicago

  • 6 guests

  • 3 bedrooms

£1,262 night

This stylish home-from-home is in Chicago’s artistic and culinary zeitgeist – South Loop. A cool and creative neighbourhood, known for its lively music scene, bold architecture and history, you’re within walking distance from the Museum Campus and Art Institute – perfect for city-breakers and culture vultures alike.

Indigo Wabash

Indigo Wabash

Chicago Loop, Chicago

  • 4 guests

  • 2 bedrooms

£652 night

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.

Skyscraper

Skyscraper

Near North, Chicago

  • 3 guests

  • 1 bedrooms

£727 night

Arriving at this home in downtown Chicago, you’re sure to be charmed by the typically Chicagoan high rise. Gaze down on the city above, and delight in the central location in the North River district – it's famous for its abundance of galleries and arty culture.


We selected the top 3% holiday homes in Chicago

Explore the 39 most perfect homes in our collection

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Most popular homes in Chicago

Diamonds Are Forever

Diamonds Are Forever

Chicago Loop, Chicago

  • 2 guests

  • 1 bedrooms

£385 night

Flaming Saganaki

Flaming Saganaki

Greektown, Chicago

  • 4 guests

  • 1 bedrooms

£480 night

The Jeweler's Gem

The Jeweler's Gem

Chicago Loop, Chicago

  • 2 guests

  • 1 bedrooms

£324 night

On Cloud Nine

On Cloud Nine

Near North, Chicago

  • 2 guests

  • 1 bedrooms

£380 night

New Millennium

New Millennium

Chicago Loop, Chicago

  • 4 guests

  • 2 bedrooms

£525 night

Hey Mr DJ

Hey Mr DJ

South Loop, Chicago

  • 6 guests

  • 2 bedrooms

£929 night

The Jeweller

The Jeweller

Chicago Loop, Chicago

  • 2 guests

  • 1 bedrooms

£359 night

South Soul

South Soul

South Loop, Chicago

  • 2 guests

  • 1 bedrooms

£320 night

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