Two floors of city light and limestone on Chicago's most storied avenue in Chicago, IL

The Penthouse at Grand Plaza

Two floors of city light and limestone on Chicago's most storied avenue

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Residence in Chicago, IL

55-56 Mag Mile Penthouse

3 Bedrooms
2 Bathrooms
5.0 (19 Reviews)

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.

What we love about this stay

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.

High-Speed Internet

Fitness Center

Outdoor Pool

Luggage Storage

Cribs Available

Game Room

Elevator

Terrace / Patio

Beach Access

BBQ / Grill

Paid Parking

Smoke Detectors

Explore the residence

2 Bathrooms

Where you'll be staying

Chicago, IL, US

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TRAVEL WITH JOURNEY

TRAVEL WITH JOURNEY

TRAVEL WITH JOURNEY

TRAVEL WITH JOURNEY

TRAVEL WITH JOURNEY