Cook County

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Welcome to a unique urban retreat, igniting the senses, and beckoning guests to indulge in the transformative charm of West Loop. Once an industrial essence, it has blossomed into a locus of gastronomy, nightlife, and style, dazzling visitors with its fusion of historic mortar and modern vibrance. Indulge in a medley of upscale boutiques and experience antiquity come alive at the vintage market. Dance to the muse's rhythm as a smorgasbord of restaurants, bars, and melodic venues embellish your visit, gently whispering tales of a city that never sleeps. Guests are requested to adhere to our safety norms for a jovial sojourn.

The West-Loop Wavelength

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. Here, the city's ceaseless energy meets a haven of international vibes. As you step inside, the culture-imbued downtown lifestyle ebbs away to early European architecture, allowing you to luxuriate in your private sanctuary amid The Windy City's dynamic heart. Indulge in this cultural infusion where chic urban living and classic charm coexist, providing an unmatched tranquil experience for discerning guests. Your idyll awaits at the city centre where leisure and convenience come naturally.

The Urban Villa

This modern penthouse is stylish, well-located, and boasts sensational skyline views – how can you go wrong? You'll find it near the West Loop, known for its top-notch restaurants and vibrant nightlife. Exploring is a breeze here, but there's plenty to enjoy back home, too. Sprawl out on the sofa and bask in the scenery showcased by the floor-to-ceiling windows, or pad out to the balcony to take it all in. Topping it all off is access to the building's shared facilities, including a 24-hour gym, swimming pool, hot tub, outdoor terrace, and lounges. If that's not convenient, we don't know what is.

Chicagoan Idyll

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. Experience traditional Chicago history infused with Italian villa architecture and other internationally inspired design details. From the moment you step through the door of this cultural haven, you'll be swept away by its enchanting atmosphere. Immerse yourself in the warmth and elegance of the Villa Vista, a tranquil urban oasis where timeless charm blends seamlessly with contemporary comfort. Indulge your senses as you admire the breathtaking cityscape views from the rooftop terrace or unwind in the peaceful courtyard. Whether you're here for a weekend getaway or an extended stay, you'll find everything you need for a truly memorable experience at this charming Streeterville retreat.

Culture Haven

Welcome to The Fitz Gerald! To ensure safety, all guests must pass our screening process and provide proper ID. A $2,500 security deposit is required for your booking, accepted on Major Credit Cards only, per our House Rules.

The perfect urban escape, near Chicago's West Loop, with plenty of options for dining, shopping and entertainment. Featuring a private balcony with skyline views, this contemporary style gem will give you the ultimate luxury living experience.

The Lofted Escape

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.

From the living space on the lower floor of this home, you will have access to a bright courtyard allowing fresh air to flow into the home. Here, you will also find a large sculpture created by a local artist and the staircase that will take you up to the rooftop terrace. Why not enjoy your morning coffee up here each day to soak up the fantastic views? 

Catch up on important work in the dedicated office space which features a Mac desktop, a desk which can be used as a standing or seated desk, plus great views through the windows in front of you. In this room, you will also find a live Peloton bike, perfect for working up a sweat and keeping fit during your stay.

Head out and explore the area including McCormick Place and Museum Campus, both of which are roughly five minutes away from the building. Then, in the evening, return to this home which is decorated with a real phone booth and modern art, and curl up in front of the electric fireplace, settle down with a great book in the reading nook, or even slip into a relaxing bath with a glass of wine in your hand. 

Chicago Morning

Travelling with a big crew? This trio of downtown Chicago penthouses makes it a breeze. With nine bedrooms spread across three apartments, everyone gets space to themselves without missing out on the fun. Think skyline views through floor-to-ceiling windows, private balconies made for sunset drinks, and sleek kitchens perfect for group dinners. On-site perks include a rooftop pool, gym, basketball court, steam room, cinema, and even a private footbridge that takes you straight into Jewel Osco, like it’s your own pantry. And the best bit? You’re just a short stroll from Chicago’s hottest restaurants, buzzing bars, and the business district.

Metropolis Retreat

Welcome to a gem nestled in the heart of Chicago's Financial District, offering guests a unique blend of historical architecture, city excitement and stunning views over the Chicago Riverwalk. The location is unmatched, mere steps away from Millennium Park and State Street, both alive with incredible cuisine and eclectic shopping experiences. Each corner of this domicile captures the iconic charm of downtown Chicago, promising an unforgettable stay. For those seeking solace amidst the city buzz, multiple quaint spots within provide restful retreats. Please note, guests are required to undergo a screening process and provide suitable ID for their stay. We place high importance on the security and wellbeing of our guests.

Charming Chicago Charm

Welcome to The Willis! To ensure safety, all guests must pass our screening process and provide proper ID. A $2,500 security deposit is required for your booking, accepted on Major Credit Cards only, per our House Rules.

The perfect urban escape, near Chicago's West Loop, with plenty of options for dining, shopping and entertainment . Featuring a private balcony with skyline views, this contemporary style gem will give you the ultimate luxury living experience.

Metropolis Respite

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Book a stay in one of the best homes in Cook County

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