Chicago Loop Luxury Homes

Award-winning homes from £98

Who's coming along?

Adults

Age 13+

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Children

Age 1 to 12

0

Infants

Under 1

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Pets

An extra fee may apply

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Home spotlights in Chicago Loop

WindyCity Wonders

WindyCity Wonders

  • 5 guests

  • 2 bedrooms

West Loop Gate, Chicago

Immerse in the life of West Loop Gate, Chicago at this lovely rental! As a former industrial area turned dining and nightlife hub, the scene offers a unique juxtaposition.

Chicago Chic

Chicago Chic

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

This pet-friendly apartment in Downtown Chicago puts the best of the city at your feet. Millennium Park, The Art Institute, theatres, restaurants, and shops are all just a short stroll away.

The Skyline's Vision

The Skyline's Vision

  • 14 guests

  • 6 bedrooms

Fulton River District, Chicago

When you bring everyone to Chicago, you want a space that matches the occasion, and these skyline retreats near Fulton Market do exactly that. By day, the city is yours to explore: coffee and street art in the West Loop, vintage hunting at Randolph Street Market, picnics in Union Park, or a culinary crawl through some of the best restaurants in the Midwest.

Culture Haven

Culture Haven

  • 12 guests

  • 4 bedrooms

Rush & Division, Chicago

Welcome to The Hermes! Nestled in the vibrant Streeterville neighborhood, classic charm meets culture and bustling downtown lifestyle in the heart of The Windy City.


We selected the top 3% holiday homes in Chicago Loop Homes

Explore the 56 most perfect homes in our collection

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Most popular homes in Chicago Loop

All Things Glow

All Things Glow

  • 3 guests

  • 2 bedrooms

Hyde Park, Chicago

The Chi-town Charm

The Chi-town Charm

  • 3 guests

  • 2 bedrooms

West Loop, Chicago

The High Way

The High Way

  • 4 guests

  • 2 bedrooms

Rush & Division, Chicago

Artists' Rendezvous

Artists' Rendezvous

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

The West-Loop Wavelength

The West-Loop Wavelength

  • 17 guests

  • 8 bedrooms

West Loop, Chicago

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Frequently asked questions

All Plum Guide homes in Chicago Loop have been tested and approved by our team of independent home critics. These meticulous beings inspect everything –from the convenience of each house’s location right down to the art on the walls– so what you see really is what you get. Worried about thin curtains? Accessibility? Maybe wifi speed is your biggest concern? Rest assured, we obsessively check each home in Chicago Loop before approving it, so you can book with peace of mind.

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