Culture Haven
12 guests
4 bedrooms
Rush & Division, Chicago
Welcome to The Hermes! Nestled in the vibrant Streeterville neighborhood, classic charm meets culture and bustling downtown lifestyle in the heart of The Windy City.
Streeterville Weekend House Rentals
We selected the 64 homes worth renting in this location
Home spotlights in Streeterville
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
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.
The Urban Villa
6 guests
2 bedrooms
Rush & Division, Chicago
A striking interplay between tradition and trend elevates this property nestled within the vibrant Streeterville neighbourhood. Combining nostalgic tales of Chicago's history with an undercurrent of worldwide allure, it resonates an Italian villa's flair and far-reaching design sensibilities.
We selected the top 3% holiday homes in Streeterville Weekend House Rentals
Explore the 64 most perfect homes in our collection
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Frequently asked questions
Looking to book a holiday rental for the weekend in Streeterville? You've come to the right place: we’re the official selection of the world’s best homes. Our collection of weekend rentals in Streeterville come fully furnished with well-equipped kitchens, toiletries in bathrooms & all linen included. We obsessively check each home for you, so you can book with peace of mind. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.
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