South Loop Homes with Penthouse Style

Welcome to the vibrant South Loop, a thriving neighborhood in the heart of Chicago, Illinois! Nestled between the iconic skyline and the shimmering shores of Lake Michigan, the South Loop is a dynamic blend of history, culture, and modern urban living. Once an industrial hub, this area has transformed into a sought-after residential enclave, attracting young professionals, families, and art enthusiasts alike.

As you stroll through the tree-lined streets, you’ll discover a rich tapestry of attractions. The South Loop is home to the renowned Museum Campus, where you can immerse yourself in the wonders of the Field Museum, Shedd Aquarium, and Adler Planetarium. Enjoy leisurely walks in Grant Park or catch a show at the nearby Auditorium Theatre. Dining options abound, from chic eateries to cozy cafes, offering a culinary journey that reflects the city’s diverse palate.

For those seeking a touch of luxury, the South Loop boasts stunning homes with penthouse-style living. Imagine waking up to breathtaking views of the Chicago skyline and Lake Michigan from your private terrace. These exquisite residences often feature spacious layouts, modern finishes, and amenities that cater to a sophisticated lifestyle. With easy access to public transportation and major highways, commuting to the bustling business districts or exploring the city’s vibrant neighborhoods is a breeze.

Whether you’re looking for a chic penthouse or a cozy condo, the South Loop offers an unparalleled living experience that combines urban sophistication with a welcoming community spirit. Discover your dream home in this enchanting neighborhood today!

Newest South Loop Homes with Penthouse Style

$899,999

4 Beds ⋅ 4 Baths ⋅ 12756636 MLS ⋅ NEW Status

Imagine ending every day with dinner overlooking the illuminated Chicago skyline, with Willis Tower seemingly framed just for you. Welcome to Residence 2900 at 1250 S Michigan Avenue-a spectacular top-floor residence offering approximately 3,000 square feet of beautifully finished, single-level living and some of the most captivating unobstructed views in the South Loop. This is not simply a large condominium. It feels like a private home in the sky. Expansive windows and three exposures-north, west and south-fill the residence with natural light and showcase sweeping views of Chicago's iconic skyline and Lake Michigan. As evening falls, the home transforms: the city lights become the backdrop to dinner, entertaining and everyday life. Freshly painted, professionally staged and meticulously maintained, the four-bedroom, 3.5-bath residence is truly move-in ready. High-end finishes and generous room proportions create an elegant yet comfortable home equally suited to sophisticated entertaining and relaxed family living. The expansive living and dining spaces are centered around the extraordinary views and complemented by a fireplace and built-in projection system. Two private balconies extend the living space outdoors and provide multiple vantage points from which to enjoy the city and lake. The chef's kitchen offers stainless-steel appliances, abundant cabinetry and casual dining space, while the oversized primary suite provides a true private retreat with a sitting area, substantial walk-in closets and spa-inspired bath with dual vanities, soaking tub and separate shower. Three additional bedrooms provide exceptional flexibility for family, guests, home offices or fitness space. An oversized in-unit laundry area and abundant storage add a level of practicality rarely found in high-rise living. An exceptionally rare offering: up to FIVE oversized attached garage parking spaces are available for separate purchase. Spaces are individually priced from approximately $35,000-$50,000, allowing the buyer to purchase as many as desired. Finding even two parking spaces with a downtown residence can be difficult; having access to as many as five makes Residence 2900 truly unique. Residents enjoy 24-hour door staff, on-site management, a heated outdoor pool, fitness center, beautifully landscaped private park and dog run, renovated party room and hallways, bike storage and exceptional access to the lakefront, Grant Park, Museum Campus, Soldier Field, restaurants, transportation and everything Chicago has to offer.

1250 S Michigan Avenue Unit #2900, Chicago

$260,000

1 Beds ⋅ 1 Baths ⋅ 12754126 MLS ⋅ NEW Status ⋅ Chess Lofts BLDG.

Perched on the top floor with sweeping east-facing lake views, this one-bedroom loft offers the best of city living in the quaint tree lined streets of the Historic Prairie District. For those who prefer a little breathing room from the city's busiest blocks, this location offers a more residential, neighborhood feel while keeping the energy of the lakefront, South Loop, downtown and major expressways within easy reach. Dog parent? You'll especially appreciate having a dog run/park practically outside your door, making morning walks and late-night outings refreshingly easy. Lake lover? You'll love living in within 2 blocks proximity to the 18th St Walking Bridge (and Metra stop) over the Metra tracks and under Lake Shore Drive to Burnham Harbor, Museum Campus, Boat Drinks live music, the South Loops best kept secret -119 acre Northerly Island Park with overflowing with nature and migratory bird watching grounds, and 18 miles of breathtaking biking, walking, and running trails hugging the Lake Michigan coastline. Inside, soaring ceilings, exposed brick and abundant natural light bring classic loft character, while the top-floor setting and east-facing exposure deliver the star of the show: beautiful lake views. And for buyers who want city living without giving up their car, garage parking offers the convenience that's increasingly hard to find. With heat, gas and water included in the assessment, along with door staff, fitness facilities and roof deck with stunning 360 lake and skyline views, this home offers a compelling combination of views, convenience, character and value. Close to it all, without having to live in the thick of it all.

320 E 21St Street Unit #807, Chicago

$725,000

3 Beds ⋅ 2 Baths ⋅ 12725932 MLS ⋅ ACTIVE Status

Experience the best of South Loop living, where spacious interiors meet exceptional outdoor living. This beautifully maintained 3 bedroom, 2 bath penthouse residence offers nearly 1,800 square feet of thoughtfully designed living space. Spanning the entire length of the residence, the 488 square-foot private terrace creates a seamless connection between indoor and outdoor living- offering ample space for dining, entertaining, gardening, or simply relaxing. Filled with an abundance of natural light, the expansive floor plan features a spacious living room, dedicated dining area, an open kitchen with granite countertops, stainless steel appliances, rich wood cabinetry, a custom tile backsplash, and a large island with seating that enhances both the function and flow of space. The desirable split-bedroom layout provides privacy, with a spacious primary suite offering direct access to the terrace, a professionally organized walk-in closet, en suite bath featuring dual vanities, a glass-enclosed shower and separate soaking tub. Two additional generously sized bedrooms(each featuring custom closets) are conveniently located near the second full bath providing comfort and flexibility for family and guests. Hardwood floors, crown molding, recessed lighting, a separate laundry room, custom window treatments, and abundant storage throughout complete this beautifully maintained residence. A heated tandem garage parking space accommodating two vehicles is available for purchase at an additional cost - a rare and valuable convenience in the South Loop! Residents of State Place enjoy an exceptional collection of amenities, including 24-hour door staff, an outdoor pool and sundeck, directly connected to FFC fitness club, beautifully landscaped gardens, a private dog run, bike room, receiving room, and on-site management. Ideally located in the heart of the South Loop, this home is just steps from Grant Park, the Museum Campus, Lake Michigan, the Lakefront Trail, Roosevelt Collection, Target, Trader Joe's, Whole Foods, Jewel-Osco, neighborhood restaurants, cafes, parks. Public transportation with Red/Orange/Green Line stops at Roosevelt. Easy access to Lake Shore Drive, I-55, and I-90/94. Experience the best of city living from a home that's truly at the center of it all!

1133 S State Street Unit #701, Chicago

$400,000

2 Beds ⋅ 2 Baths ⋅ 12711122 MLS ⋅ ACTIVE Status

Spectacular corner penthouse residence showcasing breathtaking north-facing city views and endless western sunsets, with protected sight-lines thanks to neighboring Dearborn Park. This light-filled home offers an exceptional layout rarely found in condo living, beginning with a true welcoming foyer that creates a gracious entry. The expansive open living, dining, and kitchen area is perfectly designed for entertaining, comfortably accommodating an oversized sectional, large television, island kitchen with seating and space for a large dining table and buffet. The bright, beautifully designed kitchen anchors the space and flows seamlessly to an extra-large private balcony that feels more like an outdoor deck. With room for lounge seating, grilling, dining, and greenery, it's an ideal place to relax, entertain, and take in the sweeping skyline and sunset views. The primary suite is privately tucked down the hallway, creating separation from the main living area. The generously sized bedroom easily fits a king bed and additional furnishings, while the ensuite bath features a double vanity, ample counter space, and a separate soaking tub and shower. The second bedroom is spacious and versatile, easily accommodating both a guest room and a work-from-home setup. Additional highlights include abundant closet space and a full-size stackable in-unit washer and dryer. Situated in a solid, well-managed building, with workout facilities and bike room, this penthouse-level corner home combines privacy, space, and exceptional city views in one of Chicago's most desirable residential settings. New furnace in 2023 and refrigerator in 2025. One of the few prime ground level heated garage parking spots deeded sold separately $40,000. Located in an unbeatable South Loop location, you're just steps from Mariano's, Trader Joe's, Jewel, Target, top-rated restaurants, and convenient CTA access via the L Line and multiple bus routes. Quick access to I-90/94, 55, 290, and Lake Shore Drive makes commuting and weekend getaways effortless. Take a stroll to the Lakefront, Millennium Park, Museum Campus, or nearby dog parks, one of which is in your backyard!

5 E 14Th Place Unit #1705, Chicago

$439,000

2 Beds ⋅ 2 Baths ⋅ 12677489 MLS ⋅ ACTIVE Status ⋅ Landmark Lofts BLDG.

Landmark Lofts is an investor-friendly condo association, making this top-floor northeast-corner residence an exceptional opportunity for investors and owner-occupants. Based on estimated market rent for both the residence and deeded heated parking space, the property offers the potential for an upwards-of-6% capitalization rate, subject to buyer verification and operating assumptions. This expansive approximately 1,500-square-foot loft features 2 bedrooms, 2 full baths, soaring ceilings, oversized windows, sweeping skyline and lake views, and a private balcony. The open living and dining area flows into a renovated kitchen with quartz countertops, stainless-steel appliances, abundant cabinetry, and generous workspace. Additional highlights include an updated HVAC system, new full-size in-unit washer and dryer, a spacious primary suite with walk-in closet, dedicated storage, and deeded heated garage parking. Ideally located in the South Loop near the Loop, CTA transportation, Museum Campus, Grant Park, the lakefront, restaurants, shopping, universities, hospitals, and major employment centers. A turnkey rental condo investment with strong income potential, valuable parking revenue, and excellent owner-user flexibility. All rental and investment figures are estimates and should be independently verified by the buyer.

1516 S Wabash Avenue Unit #1102, Chicago

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