Luxury Long Stay Rentals in Chicago

We selected the 41 homes worth renting in this location

Home spotlights in Chicago

South Soul

South Soul

  • 2 guests

  • 1 bedrooms

South Loop, Chicago

Looking for a stylish bolthole in a buzzy pocket of Chicago? Then this smart studio apartment, located in the residential district of South Loop, might tick your boxes.

Skyscraper

Skyscraper

  • 3 guests

  • 1 bedrooms

Near North, Chicago

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.

The Jeweller

The Jeweller

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

Just a block away from Millennium Park and the Art Institute of Chicago, this neat little apartment puts you in the centre of the Windy City. It’s a three-minute walk to Millennium Park where you’ll find fountains, playparks and sculptures, including the iconic Bean.

The Jeweler's Gem

The Jeweler's Gem

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

Snug yet stylish, this studio apartment is perfect for a lone traveller or couple wanting a cosy stay in Chicago. We love the sleek design and jewel tones – fitting, seeing as this flat is situated along the famous Jewelers Row.


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

Explore the 41 most perfect homes in our collection

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Most popular homes in Chicago

Diamonds Are Forever

Diamonds Are Forever

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

Indigo Wabash

Indigo Wabash

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

Glass Shores

Glass Shores

  • 6 guests

  • 2 bedrooms

South Loop, Chicago

New Millennium

New Millennium

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

Loop In

Loop In

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

Flaming Saganaki

Flaming Saganaki

  • 4 guests

  • 1 bedrooms

Greektown, Chicago

Southern Loop

Southern Loop

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

Bears In The Park

Bears In The Park

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

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Frequently asked questions

Explore our collection of luxury Extended Stay Rentals available for you to rent in Chicago, 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 Chicago, 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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