Book Luxury Airbnb Alternatives in South Loop

We selected the 70 homes worth renting in this location

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Age 1 to 12

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Home spotlights in South Loop

The Windy City Retreat

The Windy City Retreat

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

Step into 'The Chevelle', your unexpected sanctuary nestled amidst Chicago's lively West Loop. Previously a symbol of industrial prowess, this neighborhood is now an epicenter of world-class dining and simmering nightlife.

Italian Villa Immersion

Italian Villa Immersion

  • 8 guests

  • 3 bedrooms

Rush & Division, Chicago

Immerse yourself in the experience that is The Zeus, centrally positioned in the exciting Streeterville neighborhood. Here, a unique blend of classic allure fuses with an internationally inspired design that echoes Italian villa architecture.

Chicago Vista

Chicago Vista

  • 6 guests

  • 2 bedrooms

Rush & Division, Chicago

Step inside The Leto, where classic charm mingles with vibrant culture in the bustling Streeterville neighborhood of Chicago. This locale promises an immersive experience into not only traditional Chicago history but also the nuances of Italian villa architecture and other globally inspired design details.

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.


We selected the top 3% holiday homes in South Loop Airbnb Alternatives

Explore the 70 most perfect homes in our collection

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Most popular homes in South Loop

The Heart of the Loop

The Heart of the Loop

  • 16 guests

  • 8 bedrooms

Chicago Loop, Chicago

The Chicago River Rhapsody

The Chicago River Rhapsody

  • 14 guests

  • 6 bedrooms

River West, Chicago

The West-Loop Wavelength

The West-Loop Wavelength

  • 17 guests

  • 8 bedrooms

West Loop, Chicago

The Urban Villa

The Urban Villa

  • 6 guests

  • 2 bedrooms

Rush & Division, Chicago

Chicagoan Idyll

Chicagoan Idyll

  • 6 guests

  • 3 bedrooms

River West, Chicago

The West Wind Charm

The West Wind Charm

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

Chicago Chic

Chicago Chic

  • 4 guests

  • 2 bedrooms

Chicago Loop, Chicago

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Check upcoming rates & availability for South Loop Airbnb Alternatives


Frequently asked questions

Airbnb is a shot in the dark. We meticulously vet all our homes in South Loop to ensure you won’t waste your precious holiday. Every home you'll find on Plum Guide comes fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Before being accepted into our collection, each home much pass a meticulous vetting process, culminating in a personal home visit from an independent Home Critic. Rent one of Plum Guide's luxury South Loop Airbnb Alternatives, and enjoy a long or short stay to remember. Should you need any assistance with your booking, our friendly team of experts will be on hand to guide you through the process.

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