Book Luxury Vacation Rentals in South Loop

Award-winning homes from £98

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Home spotlights in South Loop

Southern Loop

Southern Loop

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

The living is easy at this smart apartment complex located right in the heart of buzzy South Loop, a popular residential area just south of downtown. Jam-packed with expansive green parks, prestigious museums, and legendary jazz clubs, it's easy to see why Chicagoans choose to lay down roots here.

Hey Mr DJ

Hey Mr DJ

  • 6 guests

  • 2 bedrooms

South Loop, Chicago

Escape the hustle of downtown Chicago with a stay at this sleek serviced apartment in the buzzy neighbourhood of South Loop. Well-connected to downtown Boston (seventeen minutes by metro, or eight minutes in an Uber, to be precise), you can see why Chicagoans love to lay down roots here.

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.

Drive Me Loopy

Drive Me Loopy

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

Whether you are staying for work or vacation, this high-rise apartment in trendy South Loop is perfectly located for all there is to eat, drink and do. Stepping in to look around at the chic decor, you'll notice how the cool industrial vibe is softened by the warm furniture, olive-green tones and wooden flooring.


We selected the top 3% holiday homes in South Loop Vacation Rentals

Explore the 14 most perfect homes in our collection

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Most popular homes in South Loop

Panorama Place

Panorama Place

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

Let Yourself Go

Let Yourself Go

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

Dusk in the City

Dusk in the City

  • 6 guests

  • 2 bedrooms

South Loop, Chicago

South Soul

South Soul

  • 2 guests

  • 1 bedrooms

South Loop, Chicago

Monday Night

Monday Night

  • 3 guests

  • 1 bedrooms

South Loop, Chicago

Bears In The Park

Bears In The Park

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

Swing Swing

Swing Swing

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

Running Loops

Running Loops

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

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Frequently asked questions

Take a look at our collection of luxury Vacation Rentals in South Loop, Chicago, Cook County, Illinois, United States. All of the homes you'll find on Plum Guide come fully furnished with all linen, the best-equipped kitchens, and essential bathroom toiletries included. Each home is systematically reviewed before becoming part of our collection, so you can book your stay with total confidence. And if you require any assistance in finding the perfect South Loop Vacation Rentals for you, get in touch with our team of friendly experts, on hand to help with whatever you need.

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