Book Luxury Monthly Rentals in Chicago Loop

We selected the 56 homes worth renting in this location

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Adults

Age 13+

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Children

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Home spotlights in Chicago Loop

Culture Haven

Culture Haven

  • 12 guests

  • 4 bedrooms

Rush & Division, Chicago

Welcome to The Hermes! Nestled in the vibrant Streeterville neighborhood, classic charm meets culture and bustling downtown lifestyle in the heart of The Windy City.

Elevated Luxe

Elevated Luxe

  • 5 guests

  • 2 bedrooms

Fulton River District, Chicago

Welcome to The Lincoln! To ensure safety, all guests must pass our screening process and provide proper ID.

The Lofted Escape

The Lofted Escape

  • 7 guests

  • 3 bedrooms

Fulton River District, Chicago

Welcome to The Fitz Gerald! To ensure safety, all guests must pass our screening process and provide proper ID.

The Lion

The Lion

  • 5 guests

  • 2 bedrooms

Rush & Division, Chicago

This home is the perfect place to relax and enjoy your stay in Chicago. The home is located in the Gold Coast neighborhood, which is known for its luxury shops, fine dining, and lake Michigan charm.


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

Explore the 56 most perfect homes in our collection

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Most popular homes in Chicago Loop

Loop Haven

Loop Haven

  • 12 guests

  • 6 bedrooms

Chicago Loop, Chicago

The Chicago River Rhapsody

The Chicago River Rhapsody

  • 14 guests

  • 6 bedrooms

River West, Chicago

Metropolis Retreat

Metropolis Retreat

  • 18 guests

  • 9 bedrooms

Fulton River District, Chicago

Chicago Vista

Chicago Vista

  • 6 guests

  • 2 bedrooms

Rush & Division, Chicago

Chicago Chateau

Chicago Chateau

  • 12 guests

  • 6 bedrooms

River West, Chicago

Charming Chicago Charm

Charming Chicago Charm

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Chicago Chill Pad

Chicago Chill Pad

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

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Check upcoming rates & availability for Chicago Loop Monthly Rentals


Frequently asked questions

Discover the ultimate collection of luxury Monthly Rentals in Chicago Loop, 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 Loop 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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