Book Luxury Monthly Rentals in Illinois

We selected the 100 homes worth renting in this location

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Home spotlights in Illinois

Windy City Wonder

Windy City Wonder

  • 12 guests

  • 6 bedrooms

West Loop, Chicago

Planning a large group getaway to Chicago, but don’t want to get under each other’s toes? This trio of apartments in the same high-end serviced apartment complex should do the trick.

Chicago Charisma

Chicago Charisma

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Immerse yourself in the heart of downtown at this retreat tucked away in Chicago's vibrant Financial District. Each experience here invites a journey into iconic city attractions, folds back layers of historic architectural treasures, and strolls along river cruises or the fabled Riverwalk.

Loop Haven

Loop Haven

  • 12 guests

  • 6 bedrooms

Chicago Loop, Chicago

Welcome to The Jordan! Nestled in Chicago's iconic Chicago Loop, this urban oasis provides a tranquil retreat amidst the bustling cityscape.

The Windy City Retreat

The Windy City Retreat

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

Step into 'The Chevelle', your unexpected sanctuary nestled amidst Chicago's lively West Loop. Previously a symbol of industrial prowess, this neighborhood is now an epicenter of world-class dining and simmering nightlife.


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

Explore the 100 most perfect homes in our collection

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Most popular homes in Illinois

Chicago Morning

Chicago Morning

  • 8 guests

  • 4 bedrooms

Printer's Row, Chicago

Dolly's Rainbow

Dolly's Rainbow

  • 7 guests

  • 3 bedrooms

Fisk/Meharry, Nashville

Windy City Haven

Windy City Haven

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

The Chi-town Charm

The Chi-town Charm

  • 3 guests

  • 2 bedrooms

West Loop, Chicago

The West-Loop Wavelength

The West-Loop Wavelength

  • 17 guests

  • 8 bedrooms

West Loop, Chicago

Artists' Rendezvous

Artists' Rendezvous

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

The Skyline's Vision

The Skyline's Vision

  • 14 guests

  • 6 bedrooms

Fulton River District, Chicago

The West Wind Charm

The West Wind Charm

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

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Frequently asked questions

Discover the ultimate collection of luxury Monthly Rentals in 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 Illinois 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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