Central Chicago Homes with Penthouse Style

Central Chicago Homes with Penthouse Style

Welcome to Central Chicago, a vibrant neighborhood nestled in the heart of the bustling city of Chicago, Illinois. Located in Cook County, Central Chicago offers a unique blend of urban living and historic charm.

In this sought-after area, you'll find an array of stunning homes with penthouse-style living. These luxurious properties offer the epitome of sophistication and elegance, providing residents with unparalleled views of the city skyline and an abundance of natural light.

Central Chicago's penthouse-style homes are designed with meticulous attention to detail, boasting high ceilings, spacious open floor plans, and top-of-the-line finishes. Whether you're looking for a sleek contemporary penthouse or a classic and timeless design, you'll find a wide range of options to suit your taste and lifestyle.

Living in a penthouse in Central Chicago means you'll have access to a wealth of amenities and conveniences. Many of these properties feature private rooftop terraces, perfect for entertaining guests or enjoying a quiet evening under the stars. Additionally, residents can take advantage of exclusive building amenities such as fitness centers, concierge services, and secure parking.

Central Chicago is not only a prestigious place to call home, but it also offers a prime location for exploring everything the city has to offer. From world-class dining and shopping to cultural attractions and entertainment venues, you'll never run out of things to see and do.

If you're seeking a luxurious and sophisticated lifestyle in the heart of Chicago, look no further than Central Chicago's homes with penthouse-style living. Experience the epitome of urban elegance and make this vibrant neighborhood your new home.

Newest Central Chicago Homes with Penthouse Style

$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
$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
$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
$3,300,000
2 Beds ⋅ 4 Baths ⋅ 12667187 MLS ⋅ ACTIVE Status
Rare opportunity to own this Gold Coast penthouse sitting atop a uniquely constructed James Lowenberg building. This 2,500 sq. ft. luxury home designed by Marvin Herman Architects & Interiors affectionately known as "Joyau du Ciel" offers numerous high-end finishes and has been impeccably maintained. The home features floor-to-ceiling windows throughout, as well as two balconies with east- and south-facing views, offering breathtaking, unobstructed vistas of Lake Michigan and the iconic Chicago skyline. The open-concept living and dining areas flow seamlessly into a chef's kitchen featuring ample granite counter space and a full wraparound bar with seating for six or more. Timeless Crema Marfil marble flooring in a warm, subtle hue and premium custom Anigre cabinetry are the crowning touches to this elegant space. The thoughtfully designed primary suite offers a large mirrored wardrobe and luxurious individual his-and-hers full bathrooms featuring an oversized Jacuzzi tub, a rain shower, and a separate water closet. An adjacent den with full-size washer/dryer, currently used as a home office, completes this private retreat. Additional highlights include expansive attic storage space; noise-cancelling insulation behind 3/4" drywall in all exterior and interior walls; solid wood doors throughout; surround sound system and black-out drapes; two parking spaces conveniently located directly across from one another; visitor parking on a separate garage level; and access to exceptional building amenities, including a sundeck, health deck, and discounted membership opportunities with FFC Fitness. All custom furniture negotiable, including a dining table with seating for 14; an Estonia grand piano; a Herman Miller grandfather clock. Located in the heart of Chicago's prestigious Gold Coast neighborhood, this residence offers unparalleled access to some of the city's finest dining, shopping, nightlife, and lakefront attractions. Just moments from the Restaurant Triangle, Magnificent Mile, Oak Street Beach, Lakefront Trail and CTA Red Line, residents enjoy the perfect blend of vibrant urban energy and refined residential charm.

111 W Maple Street Unit #3402-3404, Chicago
$2,897,747
4 Beds ⋅ 4 Baths ⋅ 12701195 MLS ⋅ ACTIVE Status
PENTHOUSE LEVEL, 72nd Floor, 4-bedroom, NORTHEAST corner, 3320 square foot floor plan at the luxurious Water Tower Residences featuring impressive, sweeping lake, park and city views framing Navy Pier to the East exposure and up to Evanston along the Lake Michigan shoreline to the North exposure. The lake seems more like an Ocean through the 24 oversized windows with motorized shades. Your renovated residence utilized great attention to detail in this wide-open floor plan that offers enormous room sizes for easy living and gracious entertaining. Your mint and turn-key condition residence offers a spacious 4 bedroom/family room layout. This exceptional floor plan with unforgettable views from EVERY ROOM in the home features exquisite hardwood floors, surround sound, a large foyer, oversized custom designed kitchen with center island and high-end appliances, a primary suite with an oversized luxurious bath offering double sink vanity and a large shower room, two large walk-in closets and cozy sitting area. You'll appreciate the large additional bedrooms or offices, laundry room off kitchen with-in unit trash chute, large walk in storage closets, custom closets systems throughout and beautiful baths that make your place a gem. Your treasured home is perfectly located above the exclusive renovated Ritz Carlton Hotel offering you all the coveted amenities- concierge, room service, spa, fitness, indoor pool- that make you feel like you're living in a resort every day. On site valet or self- parking options available to residents and their guests. Dogs welcome too!

180 E Pearson Street Unit #7203, Chicago
$485,000
2 Beds ⋅ 2 Baths ⋅ 12700804 MLS ⋅ ACTIVE Status
Welcome to top-floor perfection in this professionally decorated 2-bedroom, 2-bathroom penthouse with heated garage parking in River North's sophisticated gallery district! Designed for seamless entertaining, the bright, open-concept layout flows naturally from a sleek stainless-steel kitchen-complete with granite countertops and a spacious breakfast bar-directly into a living room anchored by an elegant fireplace. A private balcony just outside offers front-row seats to spectacular city sunrises and sunsets. The oversized primary suite features custom wall and window treatments, a walk-in closet by Closet Works, and a dual-vanity bath with walk-in shower. The second bedroom is lofted with a custom Murphy bed and built-in cabinetry, ideal for a guest bedroom or home office. Premium details include 10-foot ceilings, floor-to-ceiling windows, Carrera marble in the second bath, and an LG washer/dryer. Best of all, you're just moments away from incredible dining, nightlife, shopping, the Red and Brown lines, Whole Foods, and Michigan Avenue.

101 W Superior Street Unit #1202, Chicago
$1,400,000
2 Beds ⋅ 2 Baths ⋅ 12700146 MLS ⋅ ACTIVE Status
Experience the pinnacle of urban luxury in this rare, 2,500-square-foot River North penthouse loft, where 14-foot timber ceilings and exposed brick meet unparalleled modern sophistication. Designed for the ultimate entertainer, the home features a stunning, recently redesigned chef's kitchen boasting custom Italian cabinetry, exquisite quartzite counters and backsplash, a SubZero refrigerator, wine and beverage fridges, a Wolf stovetop and oven with warming drawer, a Bosch dishwasher, and a Workstation sink. The two enclosed bedrooms include a lavish primary suite with heated floors, flamed-granite countertops, a dual vanity, Brizzo fixtures, a massive glass shower, and an expansive custom-organized closet. Beyond the stunning fireplace, expansive living area, and private balcony with spectacular skyline views, this residence includes full roof rights, providing the rare opportunity to create a private rooftop deck with 360-degree city views. Impeccably maintained and move-in ready, this home is perfectly situated near premier dining, shopping, and transportation and includes a deeded garage parking spot plus additional storage for an unparalleled urban lifestyle.

420 W Grand Avenue Unit #5D, Chicago
$275,000
1 Beds ⋅ 1 Baths ⋅ 12672386 MLS ⋅ ACTIVE Status
Rare opportunity to own a truly unique industrial penthouse loft in one of the Loop's most distinctive residential buildings-a converted warehouse unlike any other in the neighborhood. Located on the top floor, this exceptional residence features dramatic soaring ceilings, the highest in the building, creating an expansive and airy living space rarely found in downtown Chicago. Character and charm abound with exposed brick walls, oversized windows, and an open-concept floor plan filled with natural light and open city views. The updated kitchen showcases custom wood open shelving, ample storage, and a design that perfectly complements the loft's industrial aesthetic. Additional conveniences include in-unit laundry, fire sprinkler protection, and a flexible layout with potential to create a lofted bedroom, office, den, or additional living space. A standout feature is the rare private screened balcony-your own outdoor retreat in the heart of the city. Enjoy morning coffee, summer evenings, and fresh air while taking in the urban skyline from this exclusive and hard-to-find outdoor space. The building is investor-friendly with no rental cap and is pet-friendly for both dogs and cats. Residents enjoy access to a fitness center, bike room, and private storage lockers, all conveniently located on the fourth floor. The location offers the ultimate downtown lifestyle. Situated in the heart of the Loop, you're just steps from CTA trains and buses, providing easy access to every corner of the city, while multiple Metra lines are only a short walk away. Enjoy being moments from the Riverwalk, Millennium Park, Pritzker Pavilion, Grant Park, Lake Michigan, the Art Institute, museums, theaters, shopping, restaurants, and year-round cultural events. Whether commuting to work, exploring Chicago's lakefront, or enjoying the city's renowned arts and entertainment scene, everything is right outside your door. Explore the property in 3D! Click the 3D Tour button to walk through every detail of this remarkable penthouse loft from the comfort of your home.

20 N State Street Unit #1013, Chicago
$949,000
2 Beds ⋅ 4 Baths ⋅ 12695100 MLS ⋅ ACTIVE Status
Stunning duplex penthouse with floor to ceiling windows and panoramic views at the Caravel. Main floor has open concept kitchen with large island. Primary and second bedrooms are both en-suite. There is also a nook for a small desk. Upper level is currently set up as a family room with a half bath. Walk out to the spectacular 900 sq ft roof top with most of it already outfitted with teak decking. Stunning views of North, East and South. This is a well-run building with over 1.6M in reserves and no current special assessments. Additional storage closet included and two deeded indoor parking spaces, #124 & #143, are available for purchase for $25,000/spot. Amenities include; newer fitness center, bike room, guest suite for your overnight guests, 24-hr door staff, on-site engineer and building manager.

635 N Dearborn Street Unit #2803, Chicago
$950,000
3 Beds ⋅ 2 Baths ⋅ 12685649 MLS ⋅ ACTIVE Status ⋅ Fairbanks At Cityfront BLDG.
Perched atop The Fairbanks at Cityfront Plaza, one of Streeterville's most sought-after full-service residences, this sun-filled corner penthouse offers a rare combination of sophistication, comfort, and panoramic city views. Spanning 1,673 square feet, this highly upgraded three-bedroom, two-bathroom home is wrapped in floor-to-ceiling glass, showcasing breathtaking views of the Chicago River, Lake Michigan, Tribune Tower, Wrigley Building, and the city's iconic skyline from nearly every room. Thoughtfully designed for both entertaining and everyday living, the expansive open-concept floor plan is enhanced by soaring 10-foot ceilings, rich hardwood flooring throughout, and an abundance of natural light. At the heart of the home, the chef's kitchen is beautifully appointed with premium finishes, generous storage, and seamless flow into the living and dining spaces, creating an ideal setting for intimate gatherings and larger-scale entertaining alike. The living and dining areas open directly to a private balcony, seamlessly extending the living experience outdoors and providing a spectacular backdrop for morning coffee, evening cocktails, and Chicago's dazzling skyline. Privately positioned within the residence, the primary suite serves as a serene sanctuary above the city, complete with a spacious walk-in closet and a spa-inspired marble bath featuring dual vanities, a deep soaking tub, and an oversized glass-enclosed shower. A private balcony extends directly from the suite, creating an intimate outdoor retreat framed by sweeping skyline and lake views. Two additional bedrooms and a flexible home office alcove provide exceptional versatility for guests, family, or today's evolving lifestyle. Residents of The Fairbanks enjoy an impressive collection of amenities, including 24-hour door staff, an outdoor pool and sundeck, fitness center, resident lounge, business center, movie theater, and more. Perfectly positioned in the heart of Streeterville, just steps from Michigan Avenue, the Chicago Riverwalk, Lake Michigan, Whole Foods, Northwestern Memorial Hospital, Northwestern University, and some of the city's finest dining, shopping, and cultural attractions. Deeded garage parking available for an additional $50,000 (P-705).

240 E Illinois Street Unit #3001, Chicago
Start Your Search



The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than our company are marked with the MRED Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (the MRED logo) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The accuracy of all information, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Copyright 2026 MRED LLC. All rights reserved.

Based on information submitted to the MLS Grid as of . All data is obtained from various sources and has not been, and will not be, verified by broker or MLS Grid. MRED supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the DMCA) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@theMLSGRID.com.

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Some listings have been excluded from this website.