Luxury Long Stay Rentals in Cook County

We selected the 36 homes worth renting in this location

Who's coming along?

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 Cook County

Loop Haven

Loop Haven

  • 12 guests

  • 6 bedrooms

Chicago Loop, Chicago

Welcome to The Jordan! Nestled in Chicago's iconic Chicago Loop, this urban oasis provides a tranquil retreat amidst the bustling cityscape.

Chicago's Gemstone

Chicago's Gemstone

  • 7 guests

  • 3 bedrooms

Fulton River District, Chicago

All resting eyes behold a unique sanctuary blending urban spirit with an enchanting skyline whisper. The escape, nestled in the heart of Chicago's cherished West Loop, extends far beyond the eye, unfolding boundless options for dining, shopping, and entertainment.

Urban Vistas

Urban Vistas

  • 4 guests

  • 2 bedrooms

Rush & Division, Chicago

This Illinois apartment won us over the moment we clapped eyes on the sweeping views of Chicago’s skyline and that private balcony. But the perks don’t end there.

Windy City Wonder

Windy City Wonder

  • 12 guests

  • 6 bedrooms

West Loop, Chicago

Planning a large group getaway to Chicago, but don’t want to get under each other’s toes? This trio of apartments in the same high-end serviced apartment complex should do the trick.

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

Explore the 36 most perfect homes in our collection

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Most popular homes in Cook County

Skyline Reverie

Skyline Reverie

  • 7 guests

  • 3 bedrooms

River West, Chicago

Windy City Haven

Windy City Haven

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

The High Way

The High Way

  • 4 guests

  • 2 bedrooms

Rush & Division, Chicago

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

Italian Villa Immersion

Italian Villa Immersion

  • 8 guests

  • 3 bedrooms

Rush & Division, Chicago

Chicago Chic

Chicago Chic

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

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Check upcoming rates & availability for Cook County Long Stay Rentals

Frequently asked questions

Explore our collection of luxury Extended Stay Rentals available for you to rent in Cook County, Illinois, United States. Each and every home you'll find has been through a meticulous, multi-stage vetting process to ensure quality our guests can always count on. The Long Stay Rentals in our Cook County, Illinois, United States collection come fully furnished with well-equipped kitchens, all linens, and essential bathroom toiletries included. And if you need any assistance, our friendly team of experts is always on hand to help plan your perfect stay.

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