Book Luxury Monthly Rentals in Chicago

We selected the 36 homes worth renting in this location

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Home spotlights in Chicago

Charming River Retreat

Charming River Retreat

  • 14 guests

  • 6 bedrooms

River West, Chicago

Welcome to a true haven in the heart of Chicago's vibrant River West neighborhood. Surrounded by trendy restaurants, bars, and shops, this elegant and modern retreat offers a tranquil escape from the hustle and bustle of the city.

Chicagoan Idyll

Chicagoan Idyll

  • 6 guests

  • 3 bedrooms

River West, Chicago

This modern penthouse is stylish, well-located, and boasts sensational skyline views – how can you go wrong? You'll find it near the West Loop, known for its top-notch restaurants and vibrant nightlife.

Chicago Chic

Chicago Chic

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

This pet-friendly apartment in Downtown Chicago puts the best of the city at your feet. Millennium Park, The Art Institute, theatres, restaurants, and shops are all just a short stroll away.

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.


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

The Heart of the Loop

The Heart of the Loop

  • 16 guests

  • 8 bedrooms

Chicago Loop, Chicago

Urban Vistas

Urban Vistas

  • 4 guests

  • 2 bedrooms

Rush & Division, Chicago

Elevated Luxe

Elevated Luxe

  • 5 guests

  • 2 bedrooms

Fulton River District, Chicago

Metropolis Respite

Metropolis Respite

  • 7 guests

  • 3 bedrooms

Fulton River District, Chicago

The Lofted Escape

The Lofted Escape

  • 7 guests

  • 3 bedrooms

Fulton River District, Chicago

Metropolis Retreat

Metropolis Retreat

  • 18 guests

  • 9 bedrooms

Fulton River District, Chicago

Windy City Haven

Windy City Haven

  • 5 guests

  • 2 bedrooms

West 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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