Lake Geneva

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Sound System

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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

Here awaits The Cooke, where guest security and solace are paramount. Ensconced in the heart of Chicago's distinguished Financial District, this property is a gateway to an array of unforgettable Windy City attractions. Landmarks that whisper tales of architectural glory and river cruises that awaken the senses are but a stroll away. Amble over to Millennium Park or the Chicago Riverwalk, each reflecting city's charm in their unique ways. State Street is replete with gastronomic gems and shopping opportunities for those with an inclusive palette. Immerse in city's essence as you experience the wonders it has to offer.

Chicago Chill Pad

Set in the heart of Chicago’s buzzing West Loop, this modern apartment is the perfect base for exploring the city. Step outside and you’re moments from acclaimed restaurants, vibrant markets and cultural landmarks – but when you’re not out and about, the building has plenty to keep you entertained. Work up a sweat in the gym or yoga studio, then wind down with cocktails on the rooftop terrace as the skyline lights up around you. The apartment itself is modern and comfortable, with a private balcony for a quieter moment. We think this is a Chicago stay made for every adventure and downtime too.

The Chi-town Charm

Hair Dryer

This home is the perfect place to relax and enjoy your stay in Chicago. The home is located in the Gold Coast neighborhood, which is known for its luxury shops, fine dining, and lake Michigan charm. The home is also close to the ice skating rink at Millennium Park, so you can enjoy some winter fun.

The Lion

Outdoor Fireplace / Firepit

Planning a large group getaway to Chicago, but don’t want to get under each other’s toes? This trio of apartments in the same high-end serviced apartment complex should do the trick. In each home expect two boutique-style bedrooms and bathrooms, a made-for-action kitchen, and a private balcony to take in those sweeping vistas of West Loop. When it’s time to get together, the rooftop communal sky lounge and outdoor terraces, complete with fire pits, should do nicely. Location-wise, West Loop's local gems, including Little Italy and Union Park, are all within easy reach on foot, so having a car isn’t a dealbreaker here.

Windy City Wonder

Welcome to a dazzling retreat in the heart of West Loop. A vibrant ambience invites you to immerse yourself, enveloped by the rhythm of the city's live music and savory aromas from nearby culinary gems. Across its former industrial terrain are now an array of dining and nightlife attractions, fashion-forward boutiques and a vintage market - a palette of sensory delights at your fingertips. Comfort meets thrill in this urban oasis rich with character and eager to create memorable experiences. Please note that to ensure guest safety we have an inclusive screening process which includes ID verification.

The West Wind Charm

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Single-Level Home

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Meeting / Conference Rooms

These two modern penthouses with cityscape views are perfect for families or groups visiting Chicago – especially if you like a little more privacy. Each penthouse has three bedrooms, bathrooms, a living space and a kitchen. You'll have access to the building's shared amenities here, including a gym and yoga studio, swimming pool, grilling stations, and a coworking space for catching up on emails. Centrally located, it's a short walk from bars and restaurants, and a quick drive or bus ride from Chicago hotspots like the Old Town, Logan Square, and Fulton Market. 

Chicago Chateau

Paid Parking On Premises

Self Check-in / Check-out

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

Extra Pillows and Blankets

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

Immerse in the life of West Loop Gate, Chicago at this lovely rental! As a former industrial area turned dining and nightlife hub, the scene offers a unique juxtaposition. The streets dance with an array of restaurants and bars, offering diverse cuisine choices for everyone. The vibrant nightlife is not just limited to dining, live music venues will make your evenings pulsate with rhythm. But it's not all hustle and bustle here! Tucked quietly are upscale boutiques and a vintage market where you can embark on a treasure hunt anytime you fancy. This safe haven guarantees smooth checks ins upon valid ID verification.

WindyCity Wonders

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

Smart TV

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

Welcome to a distinguished spot nestled in the vibrant pulse of the West Loop! All visitors are skillfully screened for safety and a damage hold is acquired prior to stay. Blissfully positioned steps away from ritzy dining and euphoric nightlife venues, this loft situates you right in the hub of excitement. An eclectic blend of high-end boutiques infuse an additional dash of flair to your visit. Indulge in the nostalgic echo of yesteryears through the vintage market close by.

Windy City Haven

This Illinois apartment won us over the moment we clapped eyes on the sweeping views of Chicago’s skyline and that private balcony. But the perks don’t end there. Part of a high-end serviced apartment complex, the shared rooftop pool, terraces, and state-of-the-art health club are just as impressive. Ideal for both extended work trips and holidays, the apartment features two equally roomy bedrooms (so there’s no quibbles for best room here) and heaps of living space with a made-for-action kitchen for eating in. Rather dine out? The buzzy restaurant scene of Michigan Avenue (known as the Magnificent Mile to locals) is just a short walk away.

Urban Vistas

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Free Parking On Premises

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Access to Beach

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Welcome Hamper

Boasting a private pool and plenty of activies, this stunning waterfront home is perfect for family gatherings. It's stylish yet cosy and complemented by the waterfront setting on Saddle Lake. Boredom is impossible here, with two kayaks and a canoe to explore the water – you can also launch boats at the public beach and moor them on the private dock. Feeling active? There's a pickleball, basketball, and volleyball court, plus softball, bocce, a saltwater swimming pool, and other games. A fire pit and a hot tub complete the outdoor activities, while inside, you’ll have a pool table, karaoke machine, and an ice cream maker – the kids will never want to leave. Breweries and wineries are nearby, and you’ll be within easy reach of hiking and biking trails, including the 33-mile Kal-Haven trail.

Lakeshore Landscape

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This apartment in Chicago's Hyde Park is positively flush with luxury touches. We love the trendy, timeless design, which merges mid-century pieces with a modern flair. Take, for instance, the custom-made neon sign that hangs by the door – as soon as you step inside, your eyes will be drawn to the pinkish glow.

Whether you fancy working out on the Peloton bike or working from home at the desk in the second bedroom, this flat has something for everyone. The glossy kitchen has all the culinary get you'll need to rustle up something delicious, while the lavish spa-style bathroom is just the ticket after a long afternoon on your feet. Plop down on the caramel-coloured sofa, a refreshing cocktail in hand, and chill out with a movie night – Apple TV, Netflix, Disney+ and HBO Max are all available for you to use. Better yet, kick things up a notch with the projector in the main bedroom – we can't think of a better way to end the evening than snuggled up in the soft sheets, falling asleep to our favourite films. 

Another thing we love? The bustling locale, just a fifteen-minute drive (or twenty-five-minute ride on the ME) from downtown Chicago. Grab a bite to eat at the restaurants on 53rd Street (two blocks away), go for a jog around Promontory Point (a twenty-minute stroll), or spend sunny summer days relaxing by the lake at 57th Street Beach (twenty-seven minutes on foot).

All Things Glow

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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

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

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

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

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

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

Welcome to The Lincoln! To ensure safety, all guests must pass our screening process and provide proper ID. A $1,000 security deposit is required for your booking, accepted on Major Credit Cards only, per our House Rules.

The perfect urban escape, nestled in Chicago's vibrant Fulton River District, with an array of dining, shopping, and entertainment options just moments away. Step inside this stylish retreat to discover a world of modern comfort and luxury. Immerse yourself in the breathtaking skyline views from your private balcony, providing an awe-inspiring backdrop to create cherished memories. Indulge in a sensory experience filled with contemporary elegance and serene ambiance. This oasis of tranquility is the ideal place to unwind and recharge after exploring the bustling city. Let The Lincoln transport you into a realm of unmatched urban serenity.

Elevated Luxe

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

Step into 'The Chevelle', your unexpected sanctuary nestled amidst Chicago's lively West Loop. Previously a symbol of industrial prowess, this neighborhood is now an epicenter of world-class dining and simmering nightlife. The environs beckon with an alluring mix of upscale boutiques and a vintage market, summoning both the modern hipster and the discerning antique enthusiast. Echoes of blaring horns from steam engines are replaced by laughter, chatter, music - sounds infusing the air with life and a love for city living. As you breach the threshold of 'The Chevelle', you are greeted with safety measures designed to create a secure, comfortable environment. While security is emphasized it never overshadow the feeling of being home away from home. A little bit nostalgic, majorly comfortable, the holiday home in West Loop embraces its past even as it looks towards the future, much like Chicago itself.

The Windy City Retreat

Welcome to our charming haven, nestled in the vibrant neighborhood of River West, Chicago. This urban oasis offers a serene escape from the bustling city, allowing you to experience the best of both worlds. Immerse yourself in the tranquil ambiance of this rustic chic retreat and be captivated by its unique features. The lush, secret garden hideout is perfect for unwinding, while the picturesque river views will soothe your senses. Step inside to discover a stylishly decorated space, blending modern loft living with vintage charm. Each room is designed with comfort and relaxation in mind, offering a cozy and intimate atmosphere. Indulge in culinary delights at nearby trendy restaurants or explore the eclectic mix of shops and bars that make this neighborhood so exceptional. Experience Chicago like never before at this whimsical riverside retreat.

Westside Retreat

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

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. It's as if the heart of Italy has effortlessly merged with the pulse of The Windy City itself, filling every corner with an intoxicating sense of heritage and cosmopolitan loftiness. A rich visual feast that mirrors its bustling environment, this property provides an enriching escape. Packed with energy yet undeniably tranquil, it inspires equal parts exploration and relaxation.

Chicago Vista

Immerse yourself in the experience that is The Zeus, centrally positioned in the exciting Streeterville neighborhood. Here, a unique blend of classic allure fuses with an internationally inspired design that echoes Italian villa architecture. The traditional history of Chicago entwines brilliantly with high-end modern lifestyle preferences to create a one-of-a-kind atmosphere, tucked away in the heart of The Windy City. Surrender to the pulsing rhythm of downtown city life Meshing effortlessly with extraordinary elegance and an indescribable sense of comfort sets this dwelling resolutely apart. Please note: guests must pass verification and provide valid ID.

Italian Villa Immersion

Picture yourself unwinding amidst the spirited charm of River West in The Kane. The vivacious neighborhood edges the restful waves of the Chicago River, its boulevard bustling with inviting eateries, captivating bars, and eclectic boutiques. Nesting there harmoniously is a beguiling blend of visionary artists, dynamic professionals, and delightful families. The property respects your safety by running a careful screening process for all potential guests and to secure your comfort during your retreat, requires a security deposit that is accepted on all Major Credit Cards. So, embark on this urban exploration in peace knowing that you are supervised with the utmost diligence.

The Chicago River Rhapsody

Make a date with The Blues, a delightful haven nestled in the West Loop. This home away from home exudes an unmistakable charm, harmonising old-world coziness with a dash of modernity. This culinary and cultural hub is now among Chicago’s most desirable locations, having evolved from its industrial roots into a buzzing hotspot perfect for food lovers and night owls alike. Greet the morning sun rejuvenated, setting out on your day's adventure amidst the wealth of nearby gastronomic havens, eclectic boutiques, and vintage markets. As twilight descends, let your ears guide you through winding streets to a medley of live music venues which will serenade you into the night. Delightfully appealing yet subtly enticing is this abode's magic—welcome to a symphony of urban charm.

Artists' Rendezvous

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

Welcome to a holiday getaway nestled right in the heart of Chicago’s vibrant Financial District. Just steps from iconic attractions, revel in the rich history of the city through its grand architecture and marvel at the stunning skyline from this retreat. Imagine embarking on river cruises, strolling along the Riverwalk, or spending afternoons in Millennium Park - all at your doorstep. This downtown jewel promises a memorable vacation experience that paints a picture of authentic Chicago, where old meets new. Delight your senses with local flavours at nearby eateries or satisfy your shopping cravings on State Street. As evening falls, retreat back to comfort where modern facilities await offering solace amidst the energetic city-life.

The Heart of the Loop

This pet-friendly apartment in Downtown Chicago puts the best of the city at your feet. Millennium Park, The Art Institute, theatres, restaurants, and shops are all just a short stroll away. When you’re ready to retreat, the home’s sleek kitchen with breakfast bar and two light-filled bedrooms make a stylish sanctuary. And with shared perks like a rooftop pool overlooking the skyline, a gym, cinema, games room, and even a poker lounge, the building itself feels like a destination.

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