Gilded Frame
3 guests
1 bedrooms
Near North, Chicago
If you’re an art lover looking to visit Chicago, then you’ve come to the right place. River North, where this delightful one-bedroom is located, has the highest concentration of galleries in the US, after Manhattan.
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.
On Cloud Nine
2 guests
1 bedrooms
Near North, Chicago
Chicago isn't just known for its lively music scene and deep-dish pizza, but also for its larger-than-life architecture – after all, those skyscrapers speak for themselves. The best way to make the most of the magnificent metropolis?
Chicago Morning
8 guests
4 bedrooms
Printer's Row, Chicago
Initially designed by an architect for their family, this incredible Chicago condo has been featured in magazines and even TV commercials. Located in the heart of downtown Chicago, this home is central to the sights and activities of the area, and also boasts an incredible green, real grass rooftop terrace with views that span across the south, east, and west of the city.
Explore the 46 most perfect homes in our collection
Browse our remarkable collection of luxury Vacation Rentals for Winter in Streeterville. As only the top 3% of homes go on to become Plum Award winners, you can be certain that your chosen home will be ideal for you. Each home in our range must pass 3 rounds of testing, and comes fully furnished with a well-equipped kitchen, all linen, and essential bathroom toiletries included. Make the most of the chilly season, and wrap up warm in a comfortable Winter Holiday Rental in Streeterville. Reach out to our caring team of experts, who love nothing more than helping you discover the perfect home for your trip.
