Holiday rentals in South Loop

Professional's Playground (Fitness Center • Sauna)

Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 2 bedroom apartment offers guests all the comforts of home, whether on the road for work or play. Within walking distance are world famous attractions including: Millennium Park, The Bean, Navy Pier, Riverwalk, Soldier Field, The Field Museum, and more. Additionally, guests are merely a couple blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city.

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

Style, comfort, and convenience

Enjoy a stay at this centrally located, spacious 1st floor condo. Within a 10-minute Uber ride to West Loop, Downtown, Chinatown, Pilsen, museum campus, and medical district. Public transport is close, with a bus to the museum campus/Soldier Field 1/2 block away. Train a 15 min walk. This 1,050 sq ft condo includes a full dining room and living room. Nearby are Target, CVS, Jewel, Whole Foods, and the "Chicago Fire" filming location. All amenities within a 2-mile radius for your convenience.

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.

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.

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!

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!

Little Italy Historic Restoration Row House

Location, location... fully rehabbed, historic 1884 row house w/2 Queen bedrooms and 2 bathrooms across from Arrigo Park in safe, quaint Little Italy. UIC campus, Rush University Medical Center and Illinois Medical District are blocks away. United Center is 17 minute walk and downtown sightseeing easily accessible by nearby public transportation. Fujitsu heating/AC units for individual comfort. Beautiful professionally maintained gardens outside your door.

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.

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.

Stunning Corner 2BR in the Loop | City & Lake View

Dramatic 1,250+ square foot corner apartment with 12 foot tall ceilings, massive windows, and panoramic city and lake views in multiple directions. This stylish light-filled two bedroom, two bathroom space is perfect for groups looking for a luxurious getaway in the sky in the heart of downtown Chicago. Centrally located in a historic building close to everything you want to visit, this is the best location in the city!

South Loop Studio Hotel (305)

Stay in the center of the action in this one-of-a-kind place! You’ll be within walking distance of Chicago's most iconic landmarks. ⚠️ Please Note: Our elevator is currently undergoing repairs. All guests will need to use the stairs to access the unit. We apologize for the inconvenience and appreciate your understanding as we maintain our unique space!