All Things Glow
3 guests
2 bedrooms
Hyde Park, Chicago
This apartment in Chicago's Hyde Park is positively flush with luxury touches. We love the trendy, timeless design, which merges mid-century pieces with a modern flair.
Streeterville Weekend House Rentals
We selected the 64 homes worth renting in this location
Home spotlights in Streeterville
Chicagoan Idyll
6 guests
3 bedrooms
River West, Chicago
This modern penthouse is stylish, well-located, and boasts sensational skyline views – how can you go wrong? You'll find it near the West Loop, known for its top-notch restaurants and vibrant nightlife.
Chicago Heights
4 guests
2 bedrooms
Chicago Loop, Chicago
This pet-friendly apartment in Downtown Chicago puts the city right at your feet, with Millennium Park, The Art Institute, theatres, and shopping just a stroll away. Inside, floor-to-ceiling windows in the main bedroom frame the skyline, while a sleek kitchen with a breakfast bar and a light-filled living space make staying in just as tempting as going out.
The Skyline's Vision
14 guests
6 bedrooms
Fulton River District, Chicago
When you bring everyone to Chicago, you want a space that matches the occasion, and these skyline retreats near Fulton Market do exactly that. By day, the city is yours to explore: coffee and street art in the West Loop, vintage hunting at Randolph Street Market, picnics in Union Park, or a culinary crawl through some of the best restaurants in the Midwest.
We selected the top 3% holiday homes in Streeterville Weekend House Rentals
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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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