Book Luxury Monthly Rentals in Chicago Loop

We selected the 34 homes worth renting in this location

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Home spotlights in Chicago Loop

Panorama Place

Panorama Place

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

Chicago is laid out at your feet thanks to the floor-to-ceiling windows of this home. Whether you're watching TV in the white living space, cooking up a feast in the pine kitchen or waking up on the memory foam mattresses in the bedrooms, the skyline is visible.

Chicago Morning

Chicago Morning

  • 8 guests

  • 4 bedrooms

Printer's Row, Chicago

Initially designed by an architect for their family, this incredible Chicago condo has been featured in magazines and even TV commercials. Located in the heart of downtown Chicago, this home is central to the sights and activities of the area, and also boasts an incredible green, real grass rooftop terrace with views that span across the south, east, and west of the city.

Monday Night

Monday Night

  • 3 guests

  • 1 bedrooms

South Loop, Chicago

Convenience is key at this stylish apartment in Chicago’s trendy River North neighbourhood. From the moment you wake up in your plush, king-size bed you'll take in sprawling city views from the floor-to-ceiling windows.

Swing Swing

Swing Swing

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

Jazz about town from this charming apartment in Chicago’s South Loop – a music hub filled with live venues, restaurants and bars. Grab a morning pick-me-up at the in-building gourmet coffee shop before heading out for a day of adventures.


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

Explore the 34 most perfect homes in our collection

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Most popular homes in Chicago Loop

Running Loops

Running Loops

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

I’m With The Band

I’m With The Band

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

Gilded Frame

Gilded Frame

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Easel And Brush

Easel And Brush

  • 5 guests

  • 2 bedrooms

Near North, Chicago

Checking Account

Checking Account

  • 2 guests

  • 1 bedrooms

Near North, Chicago

Slice Of Sky

Slice Of Sky

  • 3 guests

  • 1 bedrooms

Rush & Division, Chicago

Solo Bird

Solo Bird

  • 2 guests

  • 1 bedrooms

Near North, Chicago

Savings Account

Savings Account

  • 3 guests

  • 1 bedrooms

Near North, Chicago

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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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