Rent Luxury Cottages in Chicago

We selected the 41 homes worth renting in this location

Home spotlights in Chicago

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.

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.

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.

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.


We selected the top 3% holiday homes in Chicago Cottages

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

On Cloud Nine

On Cloud Nine

  • 2 guests

  • 1 bedrooms

Near North, Chicago

Flaming Saganaki

Flaming Saganaki

  • 4 guests

  • 1 bedrooms

Greektown, Chicago

Bears In The Park

Bears In The Park

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

Southern Loop

Southern Loop

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

Indigo Wabash

Indigo Wabash

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

New Millennium

New Millennium

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

Loop In

Loop In

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

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Frequently asked questions

Discover our curated collection of luxury holiday Cottages in Chicago, Cook County, Illinois, United States. We painstakingly review all homes available in a destination and accept only the top 3% to ensure quality our guests can trust. Each of the Chicago Cottages in our collection comes fully furnished with essential bathroom toiletries, expertly-equipped kitchens and all linens included. Book your dream stay today and should you need some help, our friendly team of experts are on hand to help plan your perfect Cottage break.

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