Book Luxury Monthly Rentals 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.

Diamonds Are Forever

Diamonds Are Forever

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

In an iconically Chicago building designed by Adler & Sullivan, this apartment sits amidst jewellery shops that have been trading since the 19th century and is just a couple of blocks from the sculpture-strewn Millennium Park. As well as old-world jewellery shops, contemporary galleries and trendy eateries fill the streets surrounding this apartment.


We selected the top 3% holiday homes in Chicago Monthly Rentals

Explore the 41 most perfect homes in our collection

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Most popular homes in Chicago

The Jeweller

The Jeweller

  • 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

Loop In

Loop In

  • 2 guests

  • 1 bedrooms

Chicago Loop, Chicago

New Millennium

New Millennium

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

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Frequently asked questions

Discover the ultimate collection of luxury Monthly Rentals in Chicago, Cook County, Illinois, United States, and say goodbye to all your travel troubles. Here at Plum Guide, it is our promise that each and every home in our range is in the top 3% of homes in its location, so there is no doubting the consistent quality we are able to offer. Secure your extended or short stay today and enjoy the trip of a lifetime in your fully furnished home, with every property on our site including all linens, essential bathroom toiletries, and a perfectly-equipped kitchen. Our meticulous home critics test everything from Wifi speed to a home's design, so you really can trust our judgement. Rent your perfect Chicago Monthly Apartment today with the help of our team of experts, on standby 24/7 to assist you with absolutely anything.

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