Printer's Row

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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

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 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

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

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

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

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

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

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

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

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

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

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Book a stay in one of the best homes in Printer's Row

We selected the 54 homes worth renting in this location

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Home spotlights in Printer's Row

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Book a stay in one of the best homes in Printer's Row

We selected the 54 homes worth renting in this location

Home spotlights in Printer&#39;s Row

We selected the top 3% holiday homes in Printer&#39;s Row

Most popular homes in Printer&#39;s Row

Check upcoming rates & availability for Printer&#39;s Row

Frequently asked questions

Can I see the best in Printer&#39;s Row?

Home spotlights in Printer's Row

We selected the top 3% holiday homes in Printer's Row

Most popular homes in Printer's Row

Check upcoming rates & availability for Printer's Row