5-Star Luxury Rentals Chicago

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.....

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 nightlif.....

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 expe.....

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 his.....

When you bring everyone to Chicago, you want a space that matches the occasion, and these skyline retreats near Fulton Market do exactly that. By day, the city is yours to explore: coffee and street a.....

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’.....

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.....

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 gem.....

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,.....

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 ar.....

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 desi.....

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.....

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 Dist.....

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.....

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 w.....

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 i.....

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.....

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 Wind.....

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.....

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.....

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 cultu.....

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-.....

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,.....

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, unfo.....

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 w.....