Book Luxury Holiday Rentals in Chicago Loop

Award-winning homes from £98

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Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

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Home spotlights in Chicago Loop

Elevated Luxe

Elevated Luxe

  • 5 guests

  • 2 bedrooms

Fulton River District, Chicago

Welcome to The Lincoln! To ensure safety, all guests must pass our screening process and provide proper ID.

Metropolis Respite

Metropolis Respite

  • 7 guests

  • 3 bedrooms

Fulton River District, Chicago

Welcome to The Willis! To ensure safety, all guests must pass our screening process and provide proper ID.

The Lion

The Lion

  • 5 guests

  • 2 bedrooms

Rush & Division, Chicago

This home is the perfect place to relax and enjoy your stay in Chicago. The home is located in the Gold Coast neighborhood, which is known for its luxury shops, fine dining, and lake Michigan charm.

Charming Chicago Charm

Charming Chicago Charm

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Welcome to a gem nestled in the heart of Chicago's Financial District, offering guests a unique blend of historical architecture, city excitement and stunning views over the Chicago Riverwalk. The location is unmatched, mere steps away from Millennium Park and State Street, both alive with incredible cuisine and eclectic shopping experiences.


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

Explore the 56 most perfect homes in our collection

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Most popular homes in Chicago Loop

Chicago Chill Pad

Chicago Chill Pad

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

WindyCity Wonders

WindyCity Wonders

  • 5 guests

  • 2 bedrooms

West Loop Gate, Chicago

Chicago's Gemstone

Chicago's Gemstone

  • 7 guests

  • 3 bedrooms

Fulton River District, Chicago

The Urban Villa

The Urban Villa

  • 6 guests

  • 2 bedrooms

Rush & Division, Chicago

Chicago Vista

Chicago Vista

  • 6 guests

  • 2 bedrooms

Rush & Division, Chicago

Chicago Morning

Chicago Morning

  • 8 guests

  • 4 bedrooms

Printer's Row, Chicago

Chicago Charisma

Chicago Charisma

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

The Windy City Retreat

The Windy City Retreat

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

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Check upcoming rates & availability for Chicago Loop Holiday Rentals


Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Chicago Loop. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Chicago Loop has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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