Book Luxury Holiday Rentals in South Loop

Award-winning homes from £98

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Home spotlights in South 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 South Loop Holiday Rentals

Explore the 34 most perfect homes in our collection

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Most popular homes in South 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

Savings Account

Savings Account

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Easel And Brush

Easel And Brush

  • 5 guests

  • 2 bedrooms

Near North, Chicago

Slice Of Sky

Slice Of Sky

  • 3 guests

  • 1 bedrooms

Rush & Division, Chicago

Gilded Frame

Gilded Frame

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Local Colour

Local Colour

  • 4 guests

  • 2 bedrooms

Near North, Chicago

Checking Account

Checking Account

  • 2 guests

  • 1 bedrooms

Near North, Chicago

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Check upcoming rates & availability for South Loop Holiday Rentals


Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in South Loop. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that South Loop has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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