Guest
Hands down the best Airbnb experience I’ve ever had

The Penthouse at Grand Plaza
The elevator opens and the city unfolds. At the 55-56 Mag Mile Penthouse, arrival is vertical, a slow ascent that trades the energy of Michigan Avenue for something more private and panoramic. This duplex residence occupies the top two floors of a landmark building along Chicago's Magnificent Mile, where floor-to-ceiling windows frame an unbroken sweep of Lake Michigan, the Chicago River, and a skyline that shifts its character with every hour of light. The architecture is grand without severity, with soaring ceilings, clean stonework, and a spatial generosity that feels closer to a private home than a hotel suite.
The penthouse is designed for both gathering and retreat. The main living area stretches across an open floor plan anchored by a full gourmet kitchen, formal dining space, and lounge seating oriented toward the views. Multiple bedrooms are spread across both levels, each appointed with premium linens and private en-suite bathrooms, offering the kind of separation and privacy that makes the residence well suited to families, celebrations, or extended stays. A wraparound terrace extends the living space outdoors, placing you above the city's rhythm with nothing between you and the horizon but open air. The interiors are appointed with a mix of contemporary furnishings and warm, neutral tones that let the architecture and the views do the work.
Below, the Magnificent Mile delivers one of the most concentrated stretches of dining, shopping, and cultural life in the country. The Art Institute, Navy Pier, and the Riverwalk are all within easy reach, and the surrounding Gold Coast and Streeterville neighborhoods offer a quieter counterpoint to Michigan Avenue's energy. The penthouse sits at the intersection of spectacle and stillness, a residence that lets you step into the city in minutes and return to something that feels entirely your own.
What lingers about the 55-56 Mag Mile Penthouse is the proportion of it all. The scale of the rooms, the reach of the skyline, the way the lake stretches north beyond the edge of the glass. This is not a place that needs to announce itself. The city does that. The penthouse simply holds you above it, unhurried and wide open, with the kind of space that makes a night feel longer and a weekend feel like a week.
The elevator opens and the city unfolds. At the 55-56 Mag Mile Penthouse, arrival is vertical, a slow ascent that trades the energy of Michigan Avenue for something more private and panoramic. This duplex residence occupies the top two floors of a landmark building along Chicago's Magnificent Mile, where floor-to-ceiling windows frame an unbroken sweep of Lake Michigan, the Chicago River, and a skyline that shifts its character with every hour of light. The architecture is grand without severity, with soaring ceilings, clean stonework, and a spatial generosity that feels closer to a private home than a hotel suite.
The penthouse is designed for both gathering and retreat. The main living area stretches across an open floor plan anchored by a full gourmet kitchen, formal dining space, and lounge seating oriented toward the views. Multiple bedrooms are spread across both levels, each appointed with premium linens and private en-suite bathrooms, offering the kind of separation and privacy that makes the residence well suited to families, celebrations, or extended stays. A wraparound terrace extends the living space outdoors, placing you above the city's rhythm with nothing between you and the horizon but open air. The interiors are appointed with a mix of contemporary furnishings and warm, neutral tones that let the architecture and the views do the work.
Below, the Magnificent Mile delivers one of the most concentrated stretches of dining, shopping, and cultural life in the country. The Art Institute, Navy Pier, and the Riverwalk are all within easy reach, and the surrounding Gold Coast and Streeterville neighborhoods offer a quieter counterpoint to Michigan Avenue's energy. The penthouse sits at the intersection of spectacle and stillness, a residence that lets you step into the city in minutes and return to something that feels entirely your own.

There's something disorienting, in the best way, about standing 55 stories above Chicago and feeling the city both impossibly close and quietly distant. This penthouse doesn't perform luxury — it simply occupies it, with soaring ceilings and walls of glass that make the skyline feel less like a backdrop and more like a living companion. The fireplace in the living area grounds the space with an unexpected warmth, tempering all that glass and altitude with something genuinely inviting. Positioned between Michigan Avenue and River North, it sits at a crossroads of culture, dining, and energy, yet the interiors feel like a private world apart. This is a place suited to someone who wants Chicago at their feet without ever feeling hurried by it.
Guest
Hands down the best Airbnb experience I’ve ever had
Guest
Jim is extremely helpful + accommodating, and the views from the penthouse are incredible. Highly recommend!
Guest
Great location and breathtaking views. The apartment is spacious and comfortable, a welcome home base during our weeklong family trip to Chicago. Helpful and communicative hosts. Right on the red line (subway) which helped us get around with ease. Grocery store in the building to stock up for the week. Highly recommend!
Guest
This property is beyond amazing. It is just as the pictures show it to be, the location is perfect, and the views are spectacular.
Guest
Beautiful home, and great location!
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