Holiday rentals in Downtown Chicago

Upscale High-Rise Apt · Rooftop Pool + Views

Stay in this brand-new 2025 apartment with luxury amenities. Perfect for work or leisure, it offers everything you need for a comfortable stay. Building Amenities: - 24/7 concierge & secure entry - Rooftop pool & gym with skyline views - Rooftop lounge with a fireplace - Steps from grocery stores & restaurants Unit Highlights: - Stunning views of the city - Black-out curtains & roller shades - Work from home space - In-unit washer & dryer - Fully equipped kitchen - Fast WiFi - Modern design

Kasa | Studio, Walk to Grant Park | South Loop

It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking distance of the Museum Campus, McCormick Place Center, and a variety of restaurants and shops. Our Kasas are the best choice for your trip to the Windy City with our spacious floorplans, full kitchen, laundry facilities, and parking. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text, phone, or chat, and a Virtual Front Desk accessed via mobile device.

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

Kasa | Views from your Private Balcony | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

Brilliant 2BR/2BA Loft I SuperHost I Sleep 6

Enjoy Chicago in our modern & spacious 2-bedroom loft in the South Loop. Central location to Grant Park, Soldier Field, Museum Campus, McCormick Place and more! Our location has a walk & transit score of 97, providing easy access to all the hot spots on your itinerary! Expect lovely natural light, luxuriously tall ceilings and room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide!

Downtown Chicago Retreat 2BD 2BA Views Gym Rooftop

Experience downtown Chicago living at its finest in this stunning 2-bedroom apartment, Sleek black and gold accents, in the heart of the River West. Wake up to breathtaking city views and step out to world-class attractions just minutes from your door. Enjoy a gourmet kitchen with high-end appliances, stylish baths, in-unit laundry, gigabit Wi-Fi, and free parking. Building amenities include a rooftop lounge and gym—perfect for business or leisure.

Pilsen Modern Chic Retreat

Welcome to your perfect getaway! This stunning 2-bedroom home is the epitome of modern chic; offering an unforgettable blend of style and comfort. Designed for up to 6 guests, the space is crafted with thoughtful architectural details and an eye for eclectic decor. Located in the heart of Pilsen, known for its vibrant art scene, trendy restaurants, & local culture, you'll be perfectly situated to explore everything Chicago has to offer.

Bright & Spacious Boho Oasis: A Warm Retreat

Discover a sun-drenched sanctuary that feels like a hidden gem. This isn't just a place to stay; it’s an airy, open-concept retreat designed for those who want to settle right in. With high ceilings and a "Modern Boho" aesthetic, the space is flooded with natural light and a warm, inviting ambiance. Nestled in a quiet, residential pocket of West Town, you’ll enjoy peaceful surroundings with the professional service of a 5-star host.

Level ◆ Brand New Luxe One Bedroom

Designed with you in mind, our One Bedroom Suites range from 560 – 698 sq ft of spacious living space boasting fully-equipped kitchen, comfortable living area, spa-inspired bathroom, bedroom with king bed and open-air balcony. Perfect for couples and corporate travelers alike, all suites also feature in-suite laundry, premium appliances, flat-screen TV with cable, complimentary WiFi and local calling. Welcome to the suite life.

LIVN West Loop Chicago Queen Studio Apartment

Experience modern city living at LIVN West Loop Chicago, a stylish loft-style apartment studio at 555 W Jackson Blvd in one of the city’s most connected neighborhoods. This newly renovated studio features a full kitchen, in-unit washer and dryer, and clean, modern interiors. Walk to Union Station and Willis Tower. You are minutes from top dining, offices, and transit, ideal for business trips, weekend stays, or longer visits.

Level Two Bedroom Suite | Fulton Market

Our Two Bedroom Suites are spacious and sophisticated boasting up to approximately 1,150 sqft of modern living space. Make a home-cooked meal in your fully equipped kitchen, host friends in your open concept living and dining area, and take in the city views on your open-air balcony. All suites also feature in-suite laundry, premium appliances, smart TV with access to your favorite streaming apps, and complimentary Wi-Fi.

Modern 3BR Apartment Near North Ave Shops

Welcome to your bright and spacious 3-bedroom Chicago retreat. Enjoy an open living area, fully equipped kitchen, and cozy bedrooms designed for both comfort and privacy. Large windows fill the space with natural light, while modern furnishings and soft tones create a calm, welcoming feel - perfect for families, groups, or business travelers seeking room to relax and recharge.