West Side Homes with Penthouse Style

West Side Homes with Penthouse Style

Welcome to the West Side neighborhood in Chicago, Illinois! Located in Cook County, this vibrant area offers a unique blend of urban living and community charm. With its rich history and diverse culture, the West Side is a popular choice for homebuyers looking for a true Chicago experience.

One of the standout features of this neighborhood is the availability of homes with penthouse-style living. If you're seeking a luxurious and elevated living experience, look no further. These penthouse-style homes offer the epitome of sophistication and style, with spacious layouts and stunning views of the city skyline.

Whether you're a young professional looking for a trendy and modern space or a family in need of more room to grow, the West Side has a range of options to suit your needs. From sleek and contemporary designs to classic and timeless architecture, there's a penthouse-style home that will capture your heart.

Living in a penthouse-style home in the West Side means you'll have access to an array of amenities and conveniences. Enjoy top-notch building facilities like fitness centers, rooftop terraces, and private parking. Plus, the neighborhood itself boasts an abundance of shops, restaurants, and entertainment options just steps away from your front door.

Don't miss out on the opportunity to experience the best of Chicago living in the West Side neighborhood. Explore the homes with penthouse-style living and discover the perfect place to call home in this vibrant and sought-after community.

Newest West Side Homes with Penthouse Style

$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
$839,999
3 Beds ⋅ 2 Baths ⋅ 12712108 MLS ⋅ ACTIVE Status
***Photos are of another unit in the same building. Unit 2N is still under construction. Buyer has the ability to customize finishes.*** Welcome to 1347 W Grand, the newest luxury addition to the ever-expanding Fulton Market neighborhood. This boutique 7-unit elevator building offers an exceptional blend of privacy and sophistication with expansive open floor plans and only two residences per floor. Experience elevated city living in this stunning new-construction simplex. Thoughtfully designed with modern elegance and exceptional attention to detail, this home is flooded with natural light through oversized windows and soaring ceilings throughout. The main living level seamlessly blends living, dining, and entertaining spaces, highlighted by wide-plank hardwood flooring and a designer chef's kitchen complete with custom floor-to-ceiling cabinetry, quartz countertops with a matching backsplash, fully integrated Thermador stainless steel appliances, an oversized waterfall island, and sophisticated matte black and brass finishes. A private terrace directly off the living room creates effortless indoor/outdoor living. The spacious primary suite offers a true retreat with a spa-inspired bath featuring luxurious quartz and ceramic tile finishes, dual vanity, oversized walk-in shower, and designer fixtures. Additional bedrooms are generously sized with ample closet space and beautifully appointed bathrooms throughout. Perfectly situated in West Fulton Market near renowned restaurants, nightlife, shopping, parks, and convenient access to downtown, this exceptional residence combines luxury finishes, functional design, and unmatched outdoor living in one of Chicago's most sought-after neighborhoods.

1347 W Grand Avenue Unit #2N, Chicago
$939,999
3 Beds ⋅ 2 Baths ⋅ 12712098 MLS ⋅ ACTIVE Status
Welcome to 1347 W Grand, the newest luxury addition to the ever-expanding Fulton Market neighborhood. This boutique 7-unit elevator building offers an exceptional blend of privacy and sophistication with expansive open floor plans and only two residences per floor. Experience elevated city living in this stunning new-construction simplex unit, featuring an incredible 200 sq. ft. private balcony with breathtaking skyline views. Thoughtfully designed with modern elegance and exceptional attention to detail, this home is flooded with natural light through oversized windows and soaring ceilings throughout. The main living level seamlessly blends living, dining, and entertaining spaces, highlighted by wide-plank hardwood flooring and a designer chef's kitchen complete with custom floor-to-ceiling cabinetry, quartz countertops with a matching backsplash, fully integrated Thermador stainless steel appliances, an oversized waterfall island, and sophisticated matte black and brass finishes. A private terrace directly off the living room creates effortless indoor/outdoor living. The spacious primary suite offers a true retreat with a spa-inspired bath featuring luxurious quartz and ceramic tile finishes, dual vanity, oversized walk-in shower, and designer fixtures. Additional bedrooms are generously sized with ample closet space and beautifully appointed bathrooms throughout. Perfectly situated in West Fulton Market near renowned restaurants, nightlife, shopping, parks, and convenient access to downtown, this exceptional residence combines luxury finishes, functional design, and unmatched outdoor living in one of Chicago's most sought-after neighborhoods.

1347 W Grand Avenue Unit #3S, Chicago
$1,079,999
2 Beds ⋅ 2 Baths ⋅ 12712083 MLS ⋅ ACTIVE Status
Welcome to 1347 W Grand, the newest luxury addition to the ever-expanding Fulton Market neighborhood. This boutique 7-unit elevator building offers an exceptional blend of privacy and sophistication with expansive open floor plans and only two residences per floor. Experience elevated city living in this stunning new-construction duplex-up featuring an incredible 1,500 sq. ft. private rooftop deck with breathtaking skyline views. Thoughtfully designed with modern elegance and exceptional attention to detail, this home is flooded with natural light through oversized windows and soaring ceilings throughout. The main living level seamlessly blends living, dining, and entertaining spaces, highlighted by wide-plank hardwood flooring and a designer chef's kitchen complete with custom floor-to-ceiling cabinetry, quartz countertops with a matching backsplash, fully integrated Thermador stainless steel appliances, an oversized waterfall island, and sophisticated matte black and brass finishes. A private terrace directly off the living room creates effortless indoor/outdoor living. The spacious primary suite offers a true retreat with a spa-inspired bath featuring luxurious quartz and ceramic tile finishes, dual vanity, oversized walk-in shower, and designer fixtures. Additional bedrooms are generously sized with ample closet space and beautifully appointed bathrooms throughout. The upper-level flex space is perfect for a home office, media room, lounge, or fitness area and leads directly to the show-stopping rooftop terrace-an entertainer's dream with panoramic Chicago skyline views. Perfectly situated in West Fulton Market near renowned restaurants, nightlife, shopping, parks, and convenient access to downtown, this exceptional residence combines luxury finishes, functional design, and unmatched outdoor living in one of Chicago's most sought-after neighborhoods.

1347 W Grand Avenue Unit #4N, Chicago
$1,079,999
3 Beds ⋅ 2 Baths ⋅ 12712066 MLS ⋅ ACTIVE Status
Welcome to 1347 W Grand, the newest luxury addition to the ever-expanding Fulton Market neighborhood. This boutique 7-unit elevator building offers an exceptional blend of privacy and sophistication with expansive open floor plans and only two residences per floor. Experience elevated city living in this stunning new-construction duplex-up featuring an incredible 1,500 sq. ft. private rooftop deck with breathtaking skyline views. Thoughtfully designed with modern elegance and exceptional attention to detail, this home is flooded with natural light through oversized windows and soaring ceilings throughout. The main living level seamlessly blends living, dining, and entertaining spaces, highlighted by wide-plank hardwood flooring and a designer chef's kitchen complete with custom floor-to-ceiling cabinetry, quartz countertops with a matching backsplash, fully integrated Thermador stainless steel appliances, an oversized waterfall island, and sophisticated matte black and brass finishes. A private terrace directly off the living room creates effortless indoor/outdoor living. The spacious primary suite offers a true retreat with a spa-inspired bath featuring luxurious quartz and ceramic tile finishes, dual vanity, oversized walk-in shower, and designer fixtures. Additional bedrooms are generously sized with ample closet space and beautifully appointed bathrooms throughout. The upper-level flex space is perfect for a home office, media room, lounge, or fitness area and leads directly to the show-stopping rooftop terrace-an entertainer's dream with panoramic Chicago skyline views. Perfectly situated in West Fulton Market near renowned restaurants, nightlife, shopping, parks, and convenient access to downtown, this exceptional residence combines luxury finishes, functional design, and unmatched outdoor living in one of Chicago's most sought-after neighborhoods.

1347 W Grand Avenue Unit #4S, Chicago
$625,000
2 Beds ⋅ 2 Baths ⋅ 12710020 MLS ⋅ ACTIVE Status
PENTHOUSE perfection in the heart of the West Loop! This rarely available 2-bedroom, 2-bath concrete loft in the highly sought-after Lofthaus has been exquisitely renovated from top to bottom, combining dramatic loft living with sophisticated modern finishes and breathtaking skyline views. Flooded with natural light, the expansive open-concept living space features soaring 18-foot ceilings, floor-to-ceiling east-facing windows, and stunning city views. Double sliding doors lead to a private 15-foot balcony, creating the perfect setting for morning coffee or evening relaxation above the city. The completely redesigned chef's kitchen serves as the centerpiece of the home and showcases custom cabinetry, a large island with breakfast bar seating, quartz countertops, designer lighting, and brand-new stainless steel appliances. Seamlessly connected to the spacious living and dining areas, the layout is ideal for both entertaining and everyday living. The primary suite offers the same dramatic floor-to-ceiling windows, organized closets, and a fully renovated spa-inspired bath featuring custom cabinetry, updated plumbing fixtures, designer tilework, a new vanity and mirror, built-in linen storage, upgraded hardware, and stylish lighting. The fully enclosed second bedroom features hardwood flooring, large transom windows for natural light and contemporary sliding barn door. The adjacent guest bath has also been completely renovated with new cabinetry, plumbing fixtures, tile, vanity, mirror, hardware, and lighting. Additional upgrades throughout the home include new 8-inch wide-plank hardwood flooring, fresh paint, updated receptacles, switches and dimmers, new door hardware, decorative light fixtures, custom closet organizers, stackable in-unit laundry, and custom window treatments. Storage cage #41 is included. Heated garage parking available for an additional $35,000. Investor-friendly building with no rental cap. Unbeatable West Loop location just steps from Randolph Street dining, Target, parks, coffee shops, nightlife, the Loop, CTA trains, Metra, and everything this vibrant neighborhood has to offer. This is truly turnkey penthouse living at its finest. Explore the property in 3D! Click the 3D button to take a virtual tour and walk through every detail.

321 S Sangamon Street Unit #908, Chicago
$610,000
2 Beds ⋅ 2 Baths ⋅ 12685869 MLS ⋅ ACTIVE Status ⋅ West Town BLDG.
Exquisite penthouse living at its finest in this sun-drenched, south-facing 2 bed/ 2 bath plus den home. Designed for both seamless entertaining and comfortable remote work, this extra-wide layout features soaring 10-foot ceilings, classic white crown molding, and beautiful east-facing windows with striking skyline views. Chef's Kitchen: Equipped with imported Italian cabinetry, sleek stainless steel counters with an integrated custom honeycomb oak island, and premium Thermador double oven, Sub-Zero, and Miele appliances. Outdoor Oasis: Enjoy fresh air from three Juliette balconies off the living area, a full balcony off the primary bedroom, and a massive private roof deck with glittering city views. Work from Home: French doors offer quiet privacy for a dedicated home office or den. Primary Suite: A true retreat featuring dual sinks, custom granite countertops, a jetted soaking tub, and a separate stone rain shower. Extras: Ample storage throughout, in-unit Bosch washer/dryer, and dedicated parking included. Perfectly situated just steps from the best restaurants and entertainment in the West Town, West Loop and Wicker Park. Easy access to I-90/290 and public transit makes commuting a breeze. Turn-key and ready for you to move right in!

1336 W Grand Avenue Unit #4, Chicago
$425,000
2 Beds ⋅ 2 Baths ⋅ 12698096 MLS ⋅ ACTIVE Status
Step into luxury living with this captivating 2 bed/2 bath penthouse, meticulously updated and nestled in a boutique concrete loft building near the vibrant West Loop. Bathed in natural light streaming through expansive east-facing windows, this home boasts an awe-inspiring open floor plan. Enjoy the grandeur of soaring 14ft+ ceilings complemented by the warmth of exposed brick in the living and primary bedroom areas. Revel in the serenity of two spacious bedrooms adorned with ample closet space, all unified by newer wood laminate flooring throughout. The heart of the home is a chef's dream, featuring a recently renovated kitchen adorned with sleek stainless steel appliances, quartz countertops, and pristine white cabinetry. Enhancing its allure is a bonus pantry complete with a built-in wine fridge, offering both functionality and style. Indulge in the convenience of in-unit laundry facilities and unwind in two updated full bathrooms showcasing modern vanities and flooring. Revel in the allure of this rental and pet-friendly building, offering a lifestyle of ease and comfort. Embrace urban living at its finest, with Union Park, Skinner Park, the United Center, public transportation, nightlife, and shopping all within walking distance. Additionally, this unit boasts roof rights, promising endless possibilities for outdoor enjoyment. Recent updates, including exterior tuckpointing/sealing in 2023, new windows in 2020, new LVT flooring throughout in 2022, brand-new HVAC in 2021, and a new dryer in 2022, ensure both contemporary comfort and peace of mind. Parking is a breeze with easy rental options available nearby starting at just $110. Don't miss your chance to experience the epitome of city living in this exquisite penthouse retreat! Investor Friendly!

1600 W Adams Street Unit #202, Chicago
$3,299,000
4 Beds ⋅ 4 Baths ⋅ 12679827 MLS ⋅ ACTIVE Status ⋅ Hale Lofts BLDG.
This Chicago loft, admired for its architectural character, sophistication, and timeless allure, has secured its place alongside those in New York and Paris as a breathtaking place to live. Unfolding across three expansive levels, this extraordinary residence offers more than 6,100 square feet of luxurious living, including over 5,100 square feet of interior space and a private 1,000-square-foot rooftop oasis. Set in the vibrant heart of Chicago's coveted West Loop, this one-of-a-kind timber-and-brick penthouse delivers luxury today, with the flexibility of tailoring the lower level to your needs for tomorrow. Crowning a boutique elevator building, the residence blends industrial soul with cosmopolitan flair. The main living level is crafted for everyday comfort and dazzling entertaining. Soaring timber ceilings, exposed brick, and a dramatic wall of commercial-grade windows fill the space with natural light and frame city views. Expansive 3000 sq ft living and dining areas flow into a chef's kitchen appointed with two of everything: double Sub-Zero refrigerators, an oversized six-burner Viking range with Bertazzoni hood, a five-burner Viking range, Bosch and Viking dishwashers, two Kalista De Giulio sinks, Taj Mahal quartzite countertops, custom Ann Sacks and Fine Line tile, and fixtures from Sherle Wagner, Waterworks, and Dornbracht. Thoughtfully curated details include bespoke built-ins, gallery-worthy art walls, wine storage, and a library channeling the timeless aura of Ralph Lauren. A dramatic, sculptural staircase anchors the home and spirals up to a private rooftop terrace. This open-air sanctuary features a gourmet outdoor kitchen, curated planters, integrated irrigation, ambient lighting, built-in heaters, and a pergola, all set against a cinematic panorama of Chicago's skyline. The lower level offers exceptional flexibility and endless possibilities for reinvention. Spanning more than 2,100 square feet, it currently features one bedroom, two baths, a vast open living area with a fireplace, ample walk-in closets, and abundant storage. This expansive space awaits your vision-be it opulent suites, 4+ bedrooms, workspaces, a private fitness studio, a state-of-the-art media lounge, or an entirely new configuration. The lower level adapts to your lifestyle and offers a clear upside for customization. A tandem garage parking space in the adjacent garage comfortably accommodates two vehicles, with additional parking available for purchase. More than a home, this West Loop loft penthouse is a statement. It offers a fully finished luxury entertaining level, a spectacular private rooftop deck, and the opportunity to customize the private bedroom level to suit your vision-all within one of Chicago's most dynamic and sought-after neighborhoods, with clear upside for the buyer.

14 N Peoria Street Unit #6H-7H, Chicago
$499,000
2 Beds ⋅ 2 Baths ⋅ 12663904 MLS ⋅ PRICE CHANGE Status
Corner penthouse residence in a boutique elevator building, offering sophisticated urban living with a thoughtfully designed open-concept floor plan and two private outdoor spaces. The sleek gourmet kitchen features custom two-tone cabinetry, quartz countertops, stainless steel appliances, and an oversized waterfall-edge peninsula that seamlessly flows into the sun-drenched living and dining area. Floor-to-ceiling European windows, two east-facing bay windows, and a private balcony (10.6' x 16') showcase abundant natural light and sweeping city views. The spacious primary suite includes two large windows, a walk-in closet, and a spa-inspired en-suite bath complete with a walk-in shower, designer tile, and a custom floating vanity. The second bedroom offers a generous closet and large window. A beautifully appointed hall bath features a soaking tub/shower combination and custom floating vanity. Additional highlights include an in-unit washer and dryer, an assigned 150-square-foot rooftop deck with panoramic skyline views, and an attached heated garage parking space included in the price. Ideally located near the West Loop, Little Italy, the United Center, and the Illinois Medical District, this home offers exceptional convenience with easy access to I-290, the CTA Blue Line, Western Avenue Metra Station (MD-N, MD-W, and NCS lines), and multiple CTA bus routes.

2342 W Adams Street Unit #505, Chicago
$574,900
2 Beds ⋅ 1 Baths ⋅ 12664400 MLS ⋅ ACTIVE Status
Unique and rarely available - Welcome to 2401 W Ohio St #34 - a hard-to-find vintage timber loft in vibrant Ukrainian Village/Smith Park! You are immediately drawn into the space with its exceptional 14'+ timber ceilings, exposed brick, and oversized windows. This expansive loft has an enviable floor plan featuring a lofted 2nd bedroom built over a fully enclosed main level bedroom. The wide main living/dining area includes a wood burning fireplace and surrounding hearth done by the owners in 2023. The full kitchen with ample work space features stainless appliances, concrete counters and a large island. A tucked away work from home office is an additional added unique feature. Unit has one full bath, washer dryer in-unit, separate mechanicals and hardwood floors throughout. On the top floor of this historic building, built in 1909, this unit has the roof rights above for future expansion of additional enclosed living space or for a private roof deck. Included is a rare deeded garage parking space conveniently located off the alley just outside the back freight elevator room. Additional, easy permit parking on Ohio just west of the building. Pet friendly. Building features a common rooftop deck with grills & lovely garden and huge original freight elevator that makes moving in easy. Entire roof was replaced in late 2024. No additional special assessments anticipated. At present only two units are rented. Easy access to 90/94 and all that West Town has to offer.

2401 W Ohio Street Unit #34, Chicago
$649,900
2 Beds ⋅ 2 Baths ⋅ 12632708 MLS ⋅ ACTIVE Status
Rarely available duplex-up penthouse condo with unobstructed views of the Chicago skyline in the West Loop! This spacious 2 bed 2 bath residence at SkyTech Lofts features 2 outdoor spaces, a private balcony of the main level and a 23' x 12' private rooftop deck with panoramic city views. The open-concept living area includes a cozy fireplace and large windows that flood the home with abundant natural light. The chef's kitchen includes stainless-steel appliances, ample cabinet space, and a dining area with room for a table for 8. Wake up to breathtaking sunrises from the Primary suite, which features a large walk-in closet with customizable Elfa shelving and ample space for a King-sized bed. A second bedroom provides versatility for guests or perfect as a home office. In unit washer/dryer and a large closet/pantry. Building amenities include a doorman, elevators, bike room, common storage, and pet-friendly policies. Located near Skinner Park and just a 5-minute walk to Fulton Market & Randolph Row. Easy access to the Green/Pink/Blue lines and I-290/I-90/94. Garage parking is available!

6 S Laflin Street Unit #911S, 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.