Book Luxury Monthly Rentals in Chicago

We selected the 36 homes worth renting in this location

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Home spotlights in Chicago

The Chicago River Rhapsody

The Chicago River Rhapsody

  • 14 guests

  • 6 bedrooms

River West, Chicago

Picture yourself unwinding amidst the spirited charm of River West in The Kane. The vivacious neighborhood edges the restful waves of the Chicago River, its boulevard bustling with inviting eateries, captivating bars, and eclectic boutiques.

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 Chateau

Chicago Chateau

  • 12 guests

  • 6 bedrooms

River West, Chicago

These two modern penthouses with cityscape views are perfect for families or groups visiting Chicago – especially if you like a little more privacy. Each penthouse has three bedrooms, bathrooms, a living space and a kitchen.

Artists' Rendezvous

Artists' Rendezvous

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

Make a date with The Blues, a delightful haven nestled in the West Loop. This home away from home exudes an unmistakable charm, harmonising old-world coziness with a dash of modernity.


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

Explore the 36 most perfect homes in our collection

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Most popular homes in Chicago

Windy City Haven

Windy City Haven

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

WindyCity Wonders

WindyCity Wonders

  • 5 guests

  • 2 bedrooms

West Loop Gate, Chicago

Chicago's Gemstone

Chicago's Gemstone

  • 7 guests

  • 3 bedrooms

Fulton River District, Chicago

Skyline Reverie

Skyline Reverie

  • 7 guests

  • 3 bedrooms

River West, Chicago

Windy City Wonder

Windy City Wonder

  • 12 guests

  • 6 bedrooms

West Loop, Chicago

The West Wind Charm

The West Wind Charm

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

The High Way

The High Way

  • 4 guests

  • 2 bedrooms

Rush & Division, Chicago

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Check upcoming rates & availability for Chicago Monthly Rentals


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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