Holiday rentals in The Loop

Plymouth Studio Suite with Gym, Rooftop, and Lobby

Welcome to The Plymouth Chicago, a historic 1899 landmark in the heart of Printers Row. Beautifully renovated in 2018 and thoughtfully redesigned in 2026, this stylish studio blends classic Chicago architecture with modern comfort. Enjoy a full kitchen, cozy living area, and in-unit laundry—perfect for longer stays. Play pool in the lobby, head up to the rooftop to grill, or workout in the gym. Just minutes from all attractions, it’s an ideal home base for business travelers and city explorers.

Location · Family · Check-in

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

Value · Location · Check-in

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.

Value · Family · Access

Spectacular 2BR Penthouse in the Loop | Roof Deck

This top floor corner penthouse is in a perfect location with panoramic city views in multiple directions. With over 1,200 square feet of space, 13 foot tall ceilings and oversized windows, this spacious penthouse is a true escape in the sky in the heart of Chicago. It's a two bedroom, two bathroom apartment with an additional sofa bed. The building has a pool and an amazing outdoor rooftop terrace with 360 degree views of the skyline and lake. This is the best location in the city!

Value · Location · Nearby

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.

Family · Value · Hospitality

1BR South Loop Loft I SuperHost + Top Rated!

Enjoy Chicago in our modern & spacious 1-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!

Value · Family · Long stay

Lovely 1-bedroom serviced apartment near Museums!

Enjoy Chicago in our modern & spacious 1-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!

Value · Family · Comfort

Loop Loft-Subway & Art Institute

Urban Elegance Meets Prime Location! Welcome to our chic hard loft in the heart of the Chicago Loop. Experience city living at its finest, where industrial charm marries modern luxury. Features: - Authentic loft with polished concrete floors - Soaring high ceilings - Elegantly furnished Location: - Right in Chicago's vibrant Loop district - Walk to Millennium Park, Art Institute of Chicago, Mag Mile, Riverwalk, and more

Value · Location · Sleep quality

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.

Value · Family · Comfort

1BR Modern Luxe Apt with In-Unit Laundry

Live your best city life in this chic West Loop 1BR/1BA! Perfect for couples, solo travelers, or remote workers, this cozy space features a comfy queen bed, full kitchen, and all the warm, modern vibes. Bring your pup or kitty—pets are totally welcome! Walk to top restaurants, cool coffee spots, and Fulton Market fun. Whether you're here to explore, work, or just chill, this inviting home is your downtown haven.

Location · Family · Cleanliness

Sentral Premium 2BR Apt South Loop Chicago

Feel at home amid the Chicago skyline. Designer details and mid-century style elevate everything you touch. An all-in-one living area gives you plenty of room to live and work. The fully equipped kitchen features marbled quartz countertops and a gas range. Please note that layout, furnishings, and views may vary by unit. A $500 credit card authorization applies at check-in and is released at checkout.

Value · Family · Hot tub

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.

Family · Value · Cleanliness