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.
Chicago Mansions
We selected the 7 homes worth renting in this location
Home spotlights
Chicago Charisma
5 guests
2 bedrooms
Chicago Loop, Chicago
Immerse yourself in the heart of downtown at this retreat tucked away in Chicago's vibrant Financial District. Each experience here invites a journey into iconic city attractions, folds back layers of historic architectural treasures, and strolls along river cruises or the fabled Riverwalk.
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.
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.
We selected the top 3% holiday homes in Chicago Mansions
Explore the 7 most perfect homes in our collection
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Frequently asked questions
Thinking of booking a mansion in Chicago? Explore our collection of holiday homes with all the luxuries of a mansion. If you're hoping for a home on the larger side, you've certainly come to the right place. Every single Plum Guide home comes fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included, so all you have to worry about is finding the home for you. Book your getaway today and stay in one of our best holiday homes in Chicago that resemble mansions.
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