South Loop Homes with Penthouse Style

Welcome to the vibrant South Loop neighborhood in Chicago, Illinois! Known for its dynamic atmosphere and convenient location, South Loop offers a unique blend of urban living and cultural experiences.

Nestled in Cook County, South Loop is a bustling district that boasts a rich history and a diverse community. Residents enjoy easy access to an array of dining options, shopping destinations, and entertainment venues. From picturesque parks to trendy boutiques, this neighborhood has something for everyone.

If you're looking for a luxurious living experience, consider exploring the Homes with Penthouse Style in South Loop. These properties redefine elegance and sophistication, offering breathtaking views of the city skyline and top-of-the-line amenities. Whether you're seeking a spacious layout or modern design features, South Loop's Penthouse Style homes are sure to impress even the most discerning homebuyer.

Don't miss the opportunity to immerse yourself in the vibrant culture and upscale living of South Loop. With its prime location and upscale housing options, this neighborhood is the perfect place to call home. Experience the best of city living in South Loop, where every day is filled with excitement and endless possibilities.

Newest South Loop Homes with Penthouse Style

$425,000

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

$269,000

1 Beds ⋅ 1 Baths ⋅ 12707558 MLS ⋅ ACTIVE Status ⋅ Chess Lofts BLDG.

Beautiful lake facing penthouse at historic Chess Lofts situated in the heart of the South Loop! Largest 1 bed floor plan in building, this spacious open floor plan loft features soaring 12 ft concrete ceilings, exposed brick, and sweeping lake and city views. The kitchen features 42" cabinets, stainless steel appliances, & granite counters. The bathroom has a newly installed vanity with quartz countertop, linen closet, and deep soaking tub. Lofted bedroom with exposed brick and huge walk-in closet! Hardwood floors throughout. In unit laundry. Storage platform and bike hooks affixed to ceiling can stay or be removed. HOA includes heat, cooking gas, trash & water. Building amenities include rooftop deck with spectacular city and lake views & exercise room. Pet friendly with dog park/run just 50 feet from the building! The Chess Lofts location cannot be beat; minutes to the Loop, Lake Michigan, Burnham Harbor, McCormick Place, Museum Campus, Northerly Island, Soldier Field, & Wintrust Arena. Steps to public transportation & easy access to LSD & expressways. +25K for heated prime parking space.

320 E 21St Street Unit #807, Chicago

$439,000

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

Wake up to spectacular sunrises over Lake Michigan and Soldier Field from this rarely available northeast corner penthouse at Landmark Lofts. Perched on the top floor with no neighbors above, this beautifully updated 2-bedroom, 2-bath home offers the perfect blend of authentic loft character, modern finishes, and unmatched privacy. Floor-to-ceiling windows wrap the living space, flooding the home with natural light and showcasing sweeping panoramic views of Lake Michigan, Soldier Field, Museum Campus, and the iconic Chicago skyline. Whether enjoying your morning coffee as the sun rises over the lake or entertaining against the backdrop of the city lights, the views are simply unforgettable. The thoughtfully remodeled kitchen is designed for both everyday living and entertaining, featuring white shaker cabinetry, quartz countertops, a large center island, light blue glass tile backsplash, sleek range hood, separate microwave, and new Frigidaire Gallery appliances. Soaring 12-foot concrete ceilings and wide-plank dark mahogany hardwood floors create a dramatic yet inviting atmosphere throughout. The spacious primary suite offers a custom walk-in closet and private en-suite bath, while the generously sized second bedroom easily accommodates guests, a home office, or both. Step outside to your private balcony-the perfect place to grill, relax, and enjoy breathtaking eastern skyline and lake views. Additional highlights include a NEW HVAC system (2026), brand-new full-size in-unit washer and dryer, one heated garage parking space, and a separate storage locker. Investor-friendly building with no rental cap, making this an exceptional opportunity for both owner-occupants and investors. Based on current market rents, the property has the potential to generate over a 5.5% capitalization rate, offering an attractive combination of lifestyle and investment performance. Located in the heart of the South Loop, Landmark Lofts is moments from Soldier Field, Museum Campus, Grant Park, Millennium Park, 12th Street Beach, Burnham Harbor, the lakefront trail, premier dining, shopping, CTA transportation, and convenient access to Lake Shore Drive, I-90/94, I-290, and I-55. Rarely does a top-floor corner loft with this combination of views, privacy, character, location, and investment potential become available. Deeded heated garage parking available for an additional $25,000.

1516 S Wabash Avenue Unit #1102, Chicago

$1,000,000

2 Beds ⋅ 2 Baths ⋅ 12652529 MLS ⋅ ACTIVE Status ⋅ Studebaker Lofts BLDG.

Step into a South Loop penthouse loft that feels more SoHo than Chicago. Set within a classic industrial building, this expansive residence blends authentic loft architecture with a warm, design-forward aesthetic rarely found in today's construction. Exposed brick walls, soaring ceilings, oversized windows, skylights, and warm maple flooring create a space that feels both dramatic and effortlessly livable. The heart of the home is an expansive open-concept living space anchored by an oversized butcher block island, reclaimed wood shelving, and a professional-grade Thermador kitchen that feels curated rather than manufactured. Natural light pours across the home throughout the day, while the scale of the living and dining areas offers the kind of volume buyers crave. Thoughtful renovations introduced custom steel-and-glass doors, updated baths, and a lofted office above the 2nd bedroom overlooking the main living space. The primary suite feels quietly luxurious with thoughtful details, and a spa-inspired bath finished with subway tile and Restoration Hardware vanity. Above it all, a private rooftop deck offers an outdoor escape rarely found - even including an outdoor shower. 3 parking spaces including a private garage included. This is a rare opportunity to own a true character-filled penthouse loft in the South Loop - the kind of space that becomes harder to find every year.

1617 S Michigan Avenue Unit #312, Chicago

$899,999

4 Beds ⋅ 4 Baths ⋅ 12462107 MLS ⋅ ACTIVE Status

Perched atop an exclusive high-rise, this extraordinary penthouse offers over 3,000 square feet of luxurious single-level living-an exceptionally rare opportunity in the heart of Chicago. Designed for effortless indoor-outdoor living, the home features two private balconies with breathtaking north, west, and south exposures, showcasing panoramic skyline and Lake Michigan views. Inside, expansive living spaces are ideal for both entertaining and everyday living. The chef's kitchen is equipped with stainless steel appliances, ample cabinetry, and a casual dining area, while the spacious living and dining room is anchored by a cozy fireplace and enhanced with a built-in projector, creating the ultimate private home theater experience. The luxurious primary suite is a true retreat, complete with a sitting area, spa-inspired bath featuring a soaking tub and separate shower, and oversized walk-in closets. Additional highlights include an oversized in-unit washer and dryer, a recently replaced HVAC unit in the corner bedroom, abundant storage, and the rare opportunity to purchase up to five attached garage parking spaces. Residents enjoy an impressive collection of full-service amenities, including 24-hour door staff, on-site management, a heated outdoor pool, fitness center, beautifully landscaped private park and dog run, newly renovated party room and hallways, and bike storage. Perfectly located with easy access to public transportation, expressways, and the CTA, this premier residence is just moments from Millennium Park, Grant Park, the Museum Campus, Soldier Field, Lake Michigan, world-class dining, shopping, and entertainment. Offering an unmatched combination of space, luxury, views, and convenience, this one-of-a-kind penthouse is truly a rare offering in one of Chicago's most sought-after neighborhoods. Explore the home in 3D-click the virtual tour button to walk through every detail.

1250 S Michigan Avenue Unit #2900, Chicago

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