Book Luxury Short Stay Rentals in Cook County

We selected the 7 homes worth renting in this location

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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

Chicago Chill Pad

Chicago Chill Pad

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Here awaits The Cooke, where guest security and solace are paramount. Ensconced in the heart of Chicago's distinguished Financial District, this property is a gateway to an array of unforgettable Windy City attractions.

Chicago Charisma

Chicago Charisma

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Immerse yourself in the heart of downtown at this retreat tucked away in Chicago's vibrant Financial District. Each experience here invites a journey into iconic city attractions, folds back layers of historic architectural treasures, and strolls along river cruises or the fabled Riverwalk.

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.

Chicago Morning

Chicago Morning

  • 8 guests

  • 4 bedrooms

Printer's Row, Chicago

Initially designed by an architect for their family, this incredible Chicago condo has been featured in magazines and even TV commercials. Located in the heart of downtown Chicago, this home is central to the sights and activities of the area, and also boasts an incredible green, real grass rooftop terrace with views that span across the south, east, and west of the city.


We selected the top 3% holiday homes in Cook County Short Stay Rentals

Explore the 7 most perfect homes in our collection

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Most popular homes

The Lion

The Lion

  • 5 guests

  • 2 bedrooms

Rush & Division, Chicago

Chicago Vista

Chicago Vista

  • 6 guests

  • 2 bedrooms

Rush & Division, Chicago

All Things Glow

All Things Glow

  • 3 guests

  • 2 bedrooms

Hyde Park, Chicago

Chicago Chill Pad

Chicago Chill Pad

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

The Lion

The Lion

  • 5 guests

  • 2 bedrooms

Rush & Division, Chicago

Cabin Retreat

Cabin Retreat

  • 8 guests

  • 3 bedrooms

Buckhorn Township, Brown County

Chicago Charisma

Chicago Charisma

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Culture Haven

Culture Haven

  • 12 guests

  • 4 bedrooms

Rush & Division, Chicago

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Check upcoming rates & availability for Cook County Short Stay Rentals


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Similar destinations

Browse our curated collection of Short Stay Rentals in Cook County, Illinois, United States. From impeccable interior design and chef-worthy kitchens, to fully furnished bathrooms and the inclusion of all linens, the homes in our collection come complete with everything you need. Each of the Cook County luxury short stay apartments in our collection has been expertly reviewed to ensure the quality standards you can trust, so book today to enjoy a getaway to remember. And should you need any assistance, our friendly team of experts are here to help you find the perfect home.

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