Streeterville Weekend House Rentals

We selected the 46 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

0

Pets

An extra fee may apply

0

Home spotlights in Streeterville

Panorama Place

Panorama Place

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

Chicago is laid out at your feet thanks to the floor-to-ceiling windows of this home. Whether you're watching TV in the white living space, cooking up a feast in the pine kitchen or waking up on the memory foam mattresses in the bedrooms, the skyline is visible.

Savings Account

Savings Account

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Are you a solo traveller or couple looking to stay in Chicago? Bookmark this page right now: you’ve found the right home-from-home with this one-bed in the arty River North district.

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.

Checking Account

Checking Account

  • 2 guests

  • 1 bedrooms

Near North, Chicago

Get out your Chicago apartment checklist and be prepared to get ticking as this apartment has all you need for your time in the Windy City. You'll find fantastic views through the floor-to-ceiling windows, ideal for admiring while you work at the desk or lounge on the sofa.


We selected the top 3% holiday homes in Streeterville Weekend House Rentals

Explore the 46 most perfect homes in our collection

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Most popular homes in Streeterville

Slice Of Sky

Slice Of Sky

  • 3 guests

  • 1 bedrooms

Rush & Division, Chicago

Gilded Frame

Gilded Frame

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Chicago Morning

Chicago Morning

  • 8 guests

  • 4 bedrooms

Printer's Row, Chicago

Local Colour

Local Colour

  • 4 guests

  • 2 bedrooms

Near North, Chicago

Bluegill

Bluegill

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Work & Play

Work & Play

  • 2 guests

  • 1 bedrooms

Near North, Chicago

Swing Swing

Swing Swing

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

Easel And Brush

Easel And Brush

  • 5 guests

  • 2 bedrooms

Near North, Chicago

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Check upcoming rates & availability for Streeterville Weekend House Rentals


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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