Chicago Loop Mansions

We selected the 56 homes worth renting in this location

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Age 13+

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Children

Age 1 to 12

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Home spotlights in Chicago Loop

The Urban Villa

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.

Chicago Vista

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.

Chicago Morning

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.

Chicago Charisma

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.


We selected the top 3% holiday homes in Chicago Loop Mansions

Explore the 56 most perfect homes in our collection

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Most popular homes in Chicago Loop

The Windy City Retreat

The Windy City Retreat

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

The West Wind Charm

The West Wind Charm

  • 5 guests

  • 2 bedrooms

West Loop, Chicago

Italian Villa Immersion

Italian Villa Immersion

  • 8 guests

  • 3 bedrooms

Rush & Division, Chicago

Skyline Reverie

Skyline Reverie

  • 7 guests

  • 3 bedrooms

River West, Chicago

The High Way

The High Way

  • 4 guests

  • 2 bedrooms

Rush & Division, Chicago

The Heart of the Loop

The Heart of the Loop

  • 16 guests

  • 8 bedrooms

Chicago Loop, Chicago

Charming River Retreat

Charming River Retreat

  • 14 guests

  • 6 bedrooms

River West, Chicago

Chicagoan Idyll

Chicagoan Idyll

  • 6 guests

  • 3 bedrooms

River West, Chicago

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Check upcoming rates & availability for Chicago Loop Mansions


Frequently asked questions

Thinking of booking a mansion in Chicago Loop? 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 Loop that resemble mansions.

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