Book Luxury Holiday 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.

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.

Bears In The Park

Bears In The Park

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

Located in Chicago’s vibrant South Loop neighbourhood, this bright and welcoming apartment puts you in an ideal position to explore some of the city’ most notable sights. Inside, warm wood floors and a cool industrial aesthetic make a stylish first impression in the main room with huge windows on two sides that allow plenty of natural light to flood in.


We selected the top 3% holiday homes in South Loop Holiday 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

Drive Me Loopy

Drive Me Loopy

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

Chicago Morning

Chicago Morning

  • 8 guests

  • 4 bedrooms

Printer's Row, Chicago

Let Yourself Go

Let Yourself Go

  • 4 guests

  • 1 bedrooms

South Loop, Chicago

Swing Swing

Swing Swing

  • 6 guests

  • 3 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

Running Loops

Running Loops

  • 6 guests

  • 3 bedrooms

South Loop, 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, Chicago, Cook County, Illinois, United States. 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, Chicago, Cook County, Illinois, United States 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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