Book Luxury Airbnb Alternatives in South Loop

We selected the 70 homes worth renting in this location

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Adults

Age 13+

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Children

Age 1 to 12

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Under 1

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Home spotlights in South Loop

WindyCity Wonders

WindyCity Wonders

  • 5 guests

  • 2 bedrooms

West Loop Gate, Chicago

Immerse in the life of West Loop Gate, Chicago at this lovely rental! As a former industrial area turned dining and nightlife hub, the scene offers a unique juxtaposition.

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.

Chicago Chill Pad

Chicago Chill Pad

  • 5 guests

  • 2 bedrooms

Chicago Loop, Chicago

Here awaits The Cooke, where guest security and solace are paramount. Ensconced in the heart of Chicago's distinguished Financial District, this property is a gateway to an array of unforgettable Windy City attractions.


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 West Wind Charm

The West Wind Charm

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

Westside Retreat

Westside Retreat

  • 7 guests

  • 3 bedrooms

River West, Chicago

The Chicago River Rhapsody

The Chicago River Rhapsody

  • 14 guests

  • 6 bedrooms

River West, Chicago

The Urban Villa

The Urban Villa

  • 6 guests

  • 2 bedrooms

Rush & Division, Chicago

Urban Vistas

Urban Vistas

  • 4 guests

  • 2 bedrooms

Rush & Division, Chicago

Windy City Haven

Windy City Haven

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

The Skyline's Vision

The Skyline's Vision

  • 14 guests

  • 6 bedrooms

Fulton River District, 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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