New Eastside

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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

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

This smart city sanctuary boasts incredible views across the Chicago skyline. The rooms have been thoughtfully designed to inspire ease and relaxation. Nespresso coffee is on hand to help get your day started and complimentary eye masks are provided to ensure a restful night’s sleep. You’ll also have access to a range of impressive amenities – including a rooftop pool, a health club, mediation lounges and a spacious terrace with fire pits and grills. Plus, the location means easy access to iconic sights, restaurants and shops.  

The High Way

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

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. Dip your toes into Millennium Park or toast with friends at spectacular dining places dotting State Street. This sanctuary envelopes you in its inviting energy, embodying an impressive passphrase to the city's captivating rhythm. Subtle strokes of enchantment are found in every corner, from enjoying skyline views to indulging in cozy moments after absorbing a day rich with exploration. Here, experiences embody adventures, evoking remnants of a day well spent, reflecting the character of stand-out architecture enveloping you. Your temporary haven urges an engagement with surroundings as it embraces you with warmth seeping from crevices of its unique construction.

Chicago Charisma

High above River West, this spectacular home with skyline views invites you to experience Chicago at its most inspiring. Floor-to-ceiling windows keep the city close at every moment, while the balcony gives you a private stage for sunrise coffees and evening cocktails under glittering lights. Spend your days exploring, whether it's the food halls of Fulton Market, art at the MCA, or strolls along the Riverwalk. Then come home to swim at sundown, gather with a glass, or simply let the skyline remind you why you came. Here, Chicago feels expansive, electric, and entirely yours.

Skyline Reverie

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

Welcome to a true haven in the heart of Chicago's vibrant River West neighborhood. Surrounded by trendy restaurants, bars, and shops, this elegant and modern retreat offers a tranquil escape from the hustle and bustle of the city. With its breathtaking views of the Chicago River, this urban oasis provides a truly unique and unforgettable experience. Immerse yourself in the cosmopolitan charm of this chic hideaway, where every corner is filled with stylish details and artistic touches. Whether you want to relax on the riverside terrace or explore the city's vibrant culture, this contemporary boutique haven is the perfect place to call home during your stay in Chicago. Experience the soothing blend of cityscape tranquility and fashionable comfort at Riverside Bliss.

Charming River Retreat

This pet-friendly apartment in Downtown Chicago puts the city right at your feet, with Millennium Park, The Art Institute, theatres, and shopping just a stroll away. Inside, floor-to-ceiling windows in the main bedroom frame the skyline, while a sleek kitchen with a breakfast bar and a light-filled living space make staying in just as tempting as going out. And to top it off, you'll have access to a range of shared amenities including a rooftop pool, gym, cinema, games room, and even a poker lounge.

Chicago Heights

All resting eyes behold a unique sanctuary blending urban spirit with an enchanting skyline whisper. The escape, nestled in the heart of Chicago's cherished West Loop, extends far beyond the eye, unfolding boundless options for dining, shopping, and entertainment. As one engages with this gem place guests find themselves embraced by a blanket of luxury sensibility without bounds. The wonder is further heightened in the private balcony serenely gazing at the skyline views, washing away all traces of mundane daily hassles, all set to embark you on a journey to rejuvenation and pure relaxation.

Chicago's Gemstone

Welcome to The Jordan! Nestled in Chicago's iconic Chicago Loop, this urban oasis provides a tranquil retreat amidst the bustling cityscape. Immerse yourself in the architecturally rich Financial District, surrounded by historic landmarks and breathtaking skyscrapers. Indulge in an enchanting experience, gazing at the mesmerizing city lights from your private rooftop terrace. Accented with modern amenities, this Metropolitan Hideaway seamlessly combines style and comfort. Explore the vibrant neighborhood filled with renowned dining and shopping destinations, or simply unwind along the scenic Chicago Riverwalk. Whether you're seeking a relaxing escape or a hub for urban adventures, The Jordan offers cosmopolitan comfort in the heart of Chicago's downtown. 

Loop Haven

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

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