Chicago Homes with Penthouse Style

Welcome to the vibrant city of Chicago, located in the heart of Illinois, in Cook County. Known for its stunning architecture, world-class dining, and rich cultural scene, Chicago offers a unique blend of urban excitement and Midwestern charm.

If you're looking for a luxurious living experience, consider exploring the exquisite homes with penthouse style in Chicago. These properties offer unparalleled views of the iconic skyline, top-of-the-line amenities, and sophisticated design elements that are sure to impress even the most discerning buyer.

Whether you're drawn to the bustling streets of downtown Chicago or the serene neighborhoods along Lake Michigan, there is a penthouse-style home that will suit your lifestyle and preferences. From sleek modern penthouses to elegant historic residences, the options are as diverse as the city itself.

Imagine waking up to panoramic views of the city, entertaining guests in your spacious living area, or unwinding in your private oasis high above the bustling streets below. With a penthouse-style home in Chicago, every day feels like a luxurious retreat.

Don't miss the opportunity to experience the height of urban living in one of Chicago's prestigious penthouse-style homes. Explore the listings and find your dream home in this dynamic city that truly has it all.

Newest Chicago Homes with Penthouse Style

$699,500

2 Beds ⋅ 2 Baths ⋅ 12716229 MLS ⋅ NEW Status

2446 W Augusta Boulevard Unit #PH, Chicago

$549,000

3 Beds ⋅ 2 Baths ⋅ 12715672 MLS ⋅ NEW Status ⋅ Opera Lofts BLDG.

A truly one-of-a-kind loft offering an extraordinary blend of history, scale, and architectural character. Once home to the original hardware used by the Lyric Opera to construct production sets, this remarkable residence showcases breathtaking 27-foot ceilings at their highest point, creating an unforgettable sense of volume and light. Thoughtfully designed across three levels, the unique open-concept layout offers exceptional flexibility with three open bedrooms, two dedicated office spaces-including one that can easily serve as an expansive walk-in dressing room-and two full bathrooms. Designed for both everyday living and effortless entertaining, the dramatic main living area flows seamlessly into the dining space and spacious kitchen. The kitchen features a large island with breakfast bar seating, abundant cabinetry, granite countertops, and stainless steel appliances. The natural stone bathrooms provide a spa-like retreat, highlighted by a luxurious primary bath with a double vanity, separate shower, and oversized jetted soaking tub. Completing this exceptional home is a private balcony showcasing city and lake views to the east, in-unit laundry, impressive storage throughout, and an attached garage parking space included in the price. Ideally located with convenient access to Lake Shore Drive, I-55, I-90/94, the lakefront, downtown Chicago, and everything the city has to offer, this is a rare opportunity to own one of Chicago's most distinctive loft residences.

2545 S Dearborn Street Unit #702, Chicago

$774,900

2 Beds ⋅ 2 Baths ⋅ 12711331 MLS ⋅ NEW Status

Stunning newer-construction penthouse in the heart of red-hot East Ukrainian Village! Thoughtfully designed with exceptional craftsmanship, premium finishes, and extensive custom upgrades throughout. The sun-drenched great room features soaring floor-to-ceiling windows, a wood-burning fireplace, and oversized sliding glass doors that open to a spacious private terrace, creating the perfect indoor-outdoor living experience. The chef's kitchen is beautifully appointed with Thermador Professional Series appliances, custom double-stacked cabinetry with glass display uppers, designer lighting, and elegant quartz countertops. Retreat to the spa-inspired primary suite featuring heated floors, a luxurious steam shower with multiple shower heads, and sophisticated porcelain tile accented by striking mosaic and hexagonal details. The beautifully finished guest bath continues the home's high-end aesthetic. A rooftop penthouse room provides the ideal space for a home office, fitness area, or staging lounge for unforgettable rooftop entertaining. The expansive private roof deck showcases breathtaking panoramic skyline and city views, while the covered outdoor living room with a fireplace creates the perfect setting for cozy evenings or entertaining year-round. With three private outdoor living spaces, this home truly embraces Chicago indoor-outdoor living. Additional highlights include hardwood floors throughout, garage parking, in-unit laundry, and dedicated storage. All of this is just steps from East Ukrainian Village's acclaimed restaurants, cafes, boutiques, parks, and nightlife-one of Chicago's most sought-after neighborhoods.

1817 W Iowa Avenue Unit #3, Chicago

$750,000

3 Beds ⋅ 2 Baths ⋅ 12714229 MLS ⋅ NEW Status

Welcome home to this stunning 3 bedroom, 2 bathroom penthouse with THREE private outdoor spaces and THREE dedicated parking spots in coveted Lincoln Park! Perfectly situated in one of Chicago's most beloved neighborhoods, this spacious and sun-drenched home delivers the perfect blend of comfort, convenience, and indoor/outdoor living. The open-concept living room boasts a cozy gas fireplace and south-facing windows that flood the home in natural light. Enjoy seamless indoor/outdoor living with the front balcony located directly off the living space - perfect for grilling, enjoying your morning coffee, or winding down in the evening. The beautifully appointed kitchen boasts crisp white shaker cabinets, granite counters, stainless steel appliances, and an island with a breakfast bar overlooking the living and dining room. Retreat to the luxurious primary suite, complete with a walk-in closet, an oversized private rear deck, and a spa-like en-suite bathroom with a double vanity, jet tub, and separate shower. Two additional generously sized bedrooms and a tastefully appointed second full bathroom. Gorgeous oak hardwood floors, high ceilings with crown molding, full-size side-by-side in-unit laundry, custom built-ins, and tons of closet/storage space throughout. Upstairs, prepare to be wowed by the ultimate summer entertaining space - your FULL massive private roof deck with breathtaking panoramic skyline views and enough space to accommodate a lounge area, fire pit, al fresco dining, and even your dream outdoor kitchen! Perhaps even more rare than the incredible outdoor space, this home includes three dedicated parking spots: one attached garage space AND a two-car exterior tandem space. Oversized bonus storage room in the basement. Unbeatable location! Enjoy everything Lincoln Park, Lakeview, and Southport Corridor have to offer, with the Brown/Purple Line just one block away and an amazing array of restaurants, coffee shops, parks, shopping, nightlife, and the lakefront all just steps from your front door. Don't miss out - this truly special home will not last long!

1010 W Diversey Parkway Unit #3, Chicago

$374,999

2 Beds ⋅ 1 Baths ⋅ 12712370 MLS ⋅ NEW Status ⋅ Capitol Hill Lofts BLDG.

West Loop Penthouse Loft. Sunny southfacing, freshly painted unit and timber residence with soaring ceilings, refined hardwood floors, skylight, and a large balcony. Features two fully enclosed bedrooms with new carpet, a spacious foyer ideal for entry and artwork, and an in-unit washer/dryer. The primary suite offers a skylight, walkin closet (8x6), and home office nook, while the second bedroom serves as a full guest room and can also serve as an office. Recent updates include a newer refrigerator and clothes dryer, freshly grouted and sealed brick walls, and replaced balcony boards. Building amenities feature secure elevator access, extra storage, bike room, and petfriendly policies with no weight or size restrictions. No rental restrictions or caps. Prime West Loop location near dining, shopping, Mary Bartelme Park, dog parks, and public transportation, with easy highway access. Enjoy all the lifestyle conveniences the West Loop has to offer. One parking space included in price

625 W Jackson Boulevard Unit #806, Chicago

$850,000

2 Beds ⋅ 2 Baths ⋅ 12714022 MLS ⋅ NEW Status ⋅ River North Commons BLDG.

RARE PROPERTY ALERT: COVETED PENTHOUSE DUPLEX LOFT WITH PRIVATE ROOFDECK in River North Commons. First time on market since 2002. Offering a rare sense of privacy and calm in the middle of the city. Spanning approximately 2,035 square feet, this 2-bedroom plus den+2nd kitchenette, 2-bath residence is designed for those who want space that feels both open and intimate. South-facing light fills the home throughout the day, while the private rooftop deck becomes an extension of your living space-quiet, elevated, and ideal for unwinding above the city. Architectural details of this home create a comfortable, grounded feel with exposed brick, large timber beams and expansive ceilings plus a true interior staircase leading to your second floor, feeling like you are in a single family home. First floor features the 2nd bedroom with murphy bed, great for 2nd bedroom, home office, or guest bedroom, a full bath, wraparound kitchen with island and breakfast bar, and expansive living room with soaring ceilings with tons of seating arrangements, full dining area, balcony perfect for grilling, and a fireplace to add a sense of ease and comfort, plus coveted pantry, and under stairs storage. Up your full interior stairs you will find your primary suite, full bath, a den/office/media room and custom kitchenette with fridge, cabinets, and sink, which offers flexibility for hosting, retreating for perfect movie nights or sporting events, or the ideal home office. This leads to the private rooftop deck with pergola, composite maintenance free decking, and privacy walls, your perfect outdoor urban oasis. The primary suite feels like a true escape, with an oversized shower with dual shower heads fit for a spa vacation, heated floors, and thoughtful built-ins elevating the space to feel organized and functional, yet elegant and tranquil. Plus you can also directly access both levels from the elevator and hallways should you ever need to avoid the stairs. Top it off with prime indoor heated garage parking ($35k) plus additional outdoor tandem parking ($25k) available and included common area storage cage. All in River North with dog park, coffee, shops, train, daycare, gyms, access to 90/94 and more out the front door. This home is not just about layout-it's about how it feels to live here: from quiet mornings and slow evenings to various live work layouts to an entertainers dream. A true home that supports an intentional life in the heart of River North.

520 W Huron Street Unit #614, Chicago

$549,900

2 Beds ⋅ 3 Baths ⋅ 12693581 MLS ⋅ NEW Status

Experience convenient city living, with stunning skyline views, in this unique two bedroom corner penthouse in an intimate elevator building ideally located in Chicago's vibrant North Center neighborhood! This split floor plan offers an expansive open concept layout and BOTH full bathrooms are ensuite. At the center of the home, the renovated kitchen features newer appliances (with a second full-size fridge), sleek contemporary cabinetry, and a herringbone backsplash. Look out the window from the island to take in the sunlight on a clear day... or step out onto your private terrace off the main living area. If you like moody walls, all you need to do is move right in and start enjoying your new space or brighten things up with a fresh coat of white paint. Easy peasy! A new furnace in 2026 can give you peace of mind. This home is perfectly nestled between the Chicago River and Western Avenue, near both Revere and Horner Parks, with easy access to the North Branch River Trail. Enjoy local restaurants, coffee shops, and boutique shopping along both Lincoln Avenue to the east, Roscoe Village to the south, and Lincoln Square to the north. Commuters will appreciate convenient access to CTA bus routes at both Irving and Western, the Brown Line at both Irving and Western, and major roadways, making travel throughout the city effortless. There is one gated exterior parking spot included in the price... and fyi, this building only offers outside parking in a clean, secure lot, plus ample free street parking next to the building. There is one secured 5'x7' personal storage unit located on the ground floor to make this a perfect 10! Welcome home.

2510 W Irving Park Road Unit #401, Chicago

$209,900

1 Beds ⋅ 1 Baths ⋅ 12686058 MLS ⋅ NEW Status

5400 S Harper Avenue Unit #1403, Chicago

$675,000

2 Beds ⋅ 2 Baths ⋅ 12707258 MLS ⋅ NEW Status

OH Canceled - Offer Accepted. You saw the bonus room on the second level leading out to the rooftop with a pergola, right? That's the difference. The difference between a true second bedroom and a makeshift guest suite that cosplays as an office from one carefully chosen Zoom angle. The difference between WFH and GTFOH. Call it an office, a gym, a home theater, or a studio. Whatever fits your life. What matters is that it gives this home something most penthouse condos simply don't have: another genuinely useful space. This pocket of Noble Square has always been one that locals quietly understand. The stretch between Ashland and the expressway is naturally constrained by Eckhardt Park, St. Boniface, and Ashland. That leaves remarkably little land left to redevelop. Ashland to Western has plenty of opportunity, but this enclave inside a submarket inside a neighborhood has very little left to give. Demand keeps finding it. Supply doesn't have many places left to grow. In other words, IYKYK. Some of Chicago's best dining is up and down Chicago Avenue, and you don't even have to leave the block for Milly's Pizza. Inside, the cathedral ceilings and exposed wood accents give the home a warmth that newer construction struggles to replicate. The updated kitchen pairs quartz countertops with a zellige backsplash, a drawer microwave tucked neatly into the cabinetry, and a wine cooler that somehow ends up being the most-used appliance. The steam shower, marble-clad primary bath feels timeless, the second bath is generously sized, and the solid masonry construction is an outlier on the block. You can measure the square footage. You have to live the difference.

1505 W Walton Street Unit #3, Chicago

$825,000

3 Beds ⋅ 2 Baths ⋅ 12710155 MLS ⋅ NEW Status

Sun-drenched penthouse offering 3 bedrooms, 2 baths, and an extraordinary private rooftop deck of approximately 600 square feet in an intimate elevator boutique building. This exceptional residence enjoys desirable southern, western, and eastern exposures, filling the home with natural light throughout the day. The thoughtfully designed open floor plan is ideal for both everyday living and entertaining. The chef's kitchen features Bosch stainless steel appliances, a generous double waterfall island, custom cabinetry, quartz countertops, and abundant storage. The spacious living and dining area centers around a gas fireplace and opens directly to a private west-facing terrace with composite decking and a gas hookup for effortless outdoor grilling. The well-appointed primary suite offers a true retreat with a custom walk-in closet and a luxurious spa-inspired bath. Two additional bedrooms include custom-organized closets and share a beautifully finished full bath. A showstopping private rooftop deck provides the ultimate outdoor oasis, complete with a custom pergola, gas hookup, and expansive space for dining, entertaining, or simply enjoying the skyline views. Additional highlights include crown moldings throughout, Hunter Douglas electric blinds throughout, a voice-activated Ecobee smart thermostat, Philips Hue smart lighting, a large private storage room with custom high-end shelving, and two side-by-side garage parking spaces in the attached heated garage. Located in the heart of Lincoln Square, this meticulously maintained home is just steps from Winnemac Park, the Brown Line, neighborhood restaurants, breweries, coffee shops, boutiques, and everything this vibrant community has to offer. A rare opportunity to own a truly move-in-ready penthouse with exceptional indoor-outdoor living.

5137 N Lincoln Avenue Unit #4S, Chicago

$635,000

2 Beds ⋅ 2 Baths ⋅ 12708185 MLS ⋅ NEW Status

Welcome to this bright and spacious top-floor two bedroom, two bathroom penthouse with a loft in the heart of Ukrainian Village. With soaring ceilings, oversized windows, and two private outdoor spaces, this home offers an open, airy feel that's hard to find. The kitchen features quartz countertops, KitchenAid stainless steel appliances, abundant custom cabinetry, and a large island with seating. Open to the living and dining areas, the layout is ideal for both everyday living and entertaining. Hardwood floors run throughout, and the front balcony just off the living room is the perfect spot for your morning coffee or an evening glass of wine. Upstairs, the loft is an ideal spot for a home office, reading area, yoga space, or Peloton, offering a quiet retreat away from the main living area. The primary suite features a walk-in closet and an en suite bathroom with a double vanity and separate glass shower. A second bedroom and beautifully renovated full bathroom provide flexible space for guests, a home office, or a growing family. The spacious rear deck enjoys southern exposure and can be accessed from either the primary suite or the common hallway, making it an ideal space for grilling, relaxing, or entertaining without guests needing to walk through the bedroom. Additional features include in-unit laundry, a covered parking space, private storage, making this home tough to beat. Located on a quiet one-way street, you're just blocks from Mariano's, neighborhood restaurants and coffee shops along Chicago Avenue, Superior Park, and public transportation, with easy access to West Loop, Wicker Park, and downtown Chicago.

Chicago

$2,000,000

3 Beds ⋅ 3 Baths ⋅ 12711621 MLS ⋅ NEW Status

Experience true penthouse living from this one-of-a-kind full-floor residence at 200 N. Dearborn, offering nearly 3,000 square feet of sophisticated interior space paired with an extraordinary 2,350-square-foot private rooftop terrace connected by a striking floating staircase. Luxury begins the moment your private elevator opens directly into an exclusive foyer, setting the stage for an impressive home designed for both grand entertaining and everyday comfort. Soaring 10-foot ceilings, dramatic oversized arched windows, and 5-inch solid white oak flooring fill the open-concept living and dining spaces with natural light while showcasing breathtaking views of the Chicago skyline, river, and Lake Michigan. The chef's kitchen is thoughtfully appointed with elegant marble countertops, custom cabinetry, and premium Wolf and Sub-Zero appliances, seamlessly connecting to the expansive living area anchored by a dramatic double-sided fireplace. The primary suite serves as a private retreat, featuring a generous walk-in closet and a spa-inspired bath complete with a two-person soaking tub, oversized steam shower with heated bench and heated floors. A spacious second en-suite bedroom enjoys spectacular lake views, while the third bedroom offers exceptional flexibility as a guest suite, home office, or media room. The showpiece of this remarkable home is the expansive private rooftop terrace, where panoramic 360-degree views of the city skyline, Chicago River, and Lake Michigan create an unforgettable backdrop. Finished with premium pavers and designed for exceptional outdoor living, the terrace includes a fully equipped outdoor kitchen with a Wolf grill, built-in pizza oven, smoker, and abundant space for dining, entertaining, or simply taking in the views. Two attached parking spaces are available for $35,000 each. A rare opportunity to own one of Chicago's most distinctive penthouse residences, combining unmatched privacy, iconic architecture, and world-class indoor-outdoor living.

200 N Dearborn Street Unit #4700, Chicago

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