Penthouses for Sale in Chicago, IL

• 

  

  

  /37

  $799,000

  • 2 Beds
  • 2 Baths
  • 1,786 Sq Ft

  1330 W Monroe St Unit 410, Chicago, IL 60607

  Duplex penthouse loft in Chicago's West Loop - one of the neighborhood's most distinctive and sought-after residences. Corner unit in the iconic Block Y complex. Two-story top floor corner unit, 2BD+Den/2BA timber loft with soaring 15-ft ceilings, exposed brick throughout, and a private ~220 SF wrap around top floor deck that gets all day sunshine and has unobstructed skyline views of the Willis

  Stephanie Turner Jameson Sotheby's Intl Realty

  1330 W Monroe St Unit 410, Chicago, IL 60607
• 

  

  

  /19

  $349,900

  Pending

  • 1 Bed
  • 1 Bath
  • 920 Sq Ft

  2800 N Lake Shore Dr Unit 2414, Chicago, IL 60657

  Stunning Southern views of the city & Lincoln Park from this upgraded high floor one bedroom, one bath with hardwood floors throughout, electronic roller shades in both living & bedroom! endless amounts of storage space from the walk-in closet to the 3 regular closets fully built out with custom organizers and drawers. This prime location offers the lake, Lincoln Park, the zoo, North Pond,

  Mary Ellen Considine Coldwell Banker Realty

  2800 N Lake Shore Dr Unit 2414, Chicago, IL 60657
• 

  

  

  /28

  $1,199,000

  $200K PRICE DROP Pending

  • 2 Beds
  • 2.5 Baths
  • 2,640 Sq Ft

  500 W Superior St Unit 2704, Chicago, IL 60654

  Magnificent one of a kind 2 bed + den, 2.1 bath Penthouse at the Montgomery with spectacular city and Lake views! Phenomenal wide floor plan With expansive living space, open floor plan perfect for living and entertaining! Elegant high end finishes thru-out, 65ft wide wall of windows, dramatic 14 foot ceilings, tremendous natural light throughout. Archilena custom kitchen w/ gourmet appliances,

  Linda Levin Jameson Sotheby's Intl Realty

  500 W Superior St Unit 2704, Chicago, IL 60654
• 

  

  

  /22

  $269,900

  $10K PRICE DROP Pending

  • 1 Bed
  • 1 Bath
  • 831 Sq Ft

  1255 S State St Unit 1913, Chicago, IL 60605

  YOU DON'T WANT TO MISS THIS ONE! BEAUTIFUL PRISTINE PENTHOUSE FLOOR LARGE ONE BEDROOM WITH FOREVER LAKE/CITY EAST VIEWS, SPACIOUS LAYOUT, BALCONY, OPEN CONCEPT KITCHEN WITH TONS OF STORAGE, HIGH CEILINGS, IN UNIT WASHER/DRYER, HARDWOOD FLOORS, SPACIOUS BATH, ABUNDANT ORGANIZED CLOSETS, SEPARATE AREA FOR SMALL OFFICE AND INCLUDES A DEEDED PARKING SPACE AND ADDITIONAL STORAGE LOCKER....BEAUTIFUL

  Sharon Rizzo RE/MAX Premier Luxury Collection

  1255 S State St Unit 1913, Chicago, IL 60605
• 

  

  

  /21

  $899,000

  • 2 Beds
  • 3 Baths
  • 2,100 Sq Ft

  550 N Saint Clair St Unit 2601, Chicago, IL 60611

  Experience luxury living in this exquisite top-floor penthouse in a contemporary high-rise, offering panoramic skyline views through floor-to-ceiling windows. The expansive open layout features hardwood floors throughout, soaring 13-foot ceilings, and two private outdoor spaces. A chef's kitchen boasts sleek Alno cabinetry, granite countertops, a breakfast bar, premium stainless steel appliances,

  Michael Dickstein @properties Christie's International Real Estate

  550 N Saint Clair St Unit 2601, Chicago, IL 60611
• 

  

  /16

  $445,000

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  4730 S Champlain Ave Unit 3, Chicago, IL 60615

  Experience modern luxury in this stunning 3-bed, 2-bath split-level penthouse. Flooded with natural light, the open layout features premium hardwood floors, 42" cabinetry, quartz countertops, an oversized island, and Energy Star stainless steel appliances. High ceilings, crown molding, custom designer lighting, and a high-efficiency HVAC system elevate every detail. The primary suite offers a

  Leah Moore Century 21 IMPACT

  4730 S Champlain Ave Unit 3, Chicago, IL 60615
• 

  

  /19

  $2,350,000

  New Construction Pending

  • 4 Beds
  • 3.5 Baths

  2679 N Orchard St Unit PHN, Chicago, IL 60614

  We are pleased to introduce 2679 N Orchard, East Lincoln Park's newest boutique luxury development. Ideally situated on an oversized lot within the highly sought-after Alcott Elementary and Lincoln Park School Districts these oversized duplex homes are a must see. This exclusive offering features four expansive duplex residences, each thoughtfully designed with four bedrooms and three-and-a-half

  Andrew Thurston Meridian Real Estate Chicago LLC

  2679 N Orchard St Unit PHN, Chicago, IL 60614
• 

  

  /36

  $1,500,000

  Pending

  • 3 Beds
  • 3 Baths

  1321 W Wrightwood Ave Unit 3, Chicago, IL 60614

  Welcome to Lincoln Park and this rare duplex-up penthouse condo on historic Wrightwood! This all-brick building benefits from an up-zoned status which allows for a bigger and wider footprint than expected. This home is truly a gem and features quality craftsmanship and luxury finishes that surpasses most new construction. The main level has a beautiful custom kitchen, living/dining space, the

  Stephanie Cutter Coldwell Banker Realty

  1321 W Wrightwood Ave Unit 3, Chicago, IL 60614
• 

  

  /29

  $599,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft

  2101 W Rice St Unit 407, Chicago, IL 60622

  Rarely available penthouse loft in the heart of Ukrainian Village, where modern updates meet timeless loft character. This beautifully reimagined 2 bed, 2 bath home offers soaring ceilings, exposed brick, oversized windows, and incredible natural light throughout. At the center of the home is a stunning, fully redesigned kitchen completed in 2026, thoughtfully curated for both everyday living and

  Gia Devenyi Jameson Sotheby's Intl Realty

  2101 W Rice St Unit 407, Chicago, IL 60622
• 

  

  /19

  $1,200,000

  $750K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,500 Sq Ft

  1120 N Lake Shore Dr Unit 18AB, Chicago, IL 60611

  Rarely available! Northeast corner penthouse with private entrance in highly desired vintage Gold Coast building. Fabulous east and north views of the lake and lakefront from many rooms and the terraces. Grand unit with cathedral carved wood ceiling in the living room. Unit is being sold by long term owner (only the second owner of the apartment) and does need renovation. Huge storage room on

  Nick Powers Baird & Warner

  1120 N Lake Shore Dr Unit 18AB, Chicago, IL 60611
• 

  

  /16

  $3,825,000

  New Construction

  • 4 Beds
  • 4.5 Baths

  224 N Elizabeth St Unit T1-2A, Chicago, IL 60607

  Fulton Bond is not just an address; it is a permanent mark on Chicago's skyline. Crafted by the visionary architects at Kohn Pedersen Fox, with bespoke interiors by MAWD | March and White Design, this collaborative masterpiece by Sulo Development bridges Fulton Market's industrial grit with the peak of modern refinement. Every monumental arch, clean line, and tailored finish honors the storied

  Mark Icuss Compass

  224 N Elizabeth St Unit T1-2A, Chicago, IL 60607
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  /56

  $1,139,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,500 Sq Ft

  545 N Dearborn St Unit W3601, Chicago, IL 60654

  Welcome to Duplex Penthouse Residence 3601 - a one-of-a-kind, custom-built, two-story private penthouse soaring above River North. Rising sky-high with dramatic 26-foot ceilings and sweeping 180 city views, this iconic residence blends art, architectural innovation, and modern luxury into a truly monumental home in the heart of downtown Chicago. Designed for an ultra-luxury lifestyle, the

  Amir Fouad @properties Christie's International Real Estate

  545 N Dearborn St Unit W3601, Chicago, IL 60654
• 

  

  /37

  $799,900

  Pending

  • 3 Beds
  • 3 Baths

  2216 N Hamilton Ave Unit 3, Chicago, IL 60647

  Stylish and spacious 3-bedroom, 3-bath duplex-up in the heart of Bucktown, offering an ideal blend of comfort, functionality, and an unbeatable location. Set in an intimate boutique building, this beautifully updated home features an expansive open-concept main level with refinished hardwood floors, updated trim and lighting, and a cozy gas fireplace. The chef's kitchen is designed for both

  Tommy Choi Keller Williams ONEChicago

  2216 N Hamilton Ave Unit 3, Chicago, IL 60647
• 

  

  /9

  $207,000

  $12K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft

  3950 N Lake Shore Dr Unit 2312, Chicago, IL 60613

  City Living at its Finest! Enjoy clear views of Lake Michigan from your living room from the 23rd floor! Sunrise over the lake and sunset views from your bedroom over the city. Beautifully maintained unit within a recently updated building, full of modern touches and amenities. Investor-friendly opportunity! This Penthouse 1BD/1BA unit offers stunning city and lake views and comes with a tenant

  Mita Nermal Shewakramani Mita Shewakramani

  3950 N Lake Shore Dr Unit 2312, Chicago, IL 60613
• 

  

  /18

  $499,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft

  1735 N Paulina St Unit 604, Chicago, IL 60622

  Rare Corner Penthouse Loft in Historic Pac Lofts | Bucktown. Experience authentic loft living in this rarely available top-floor corner residence at the iconic Pac Lofts in the heart of Bucktown. A true Chicago loft conversion, this home showcases the architectural character buyers seek, including soaring concrete ceilings, exposed brick, and expansive industrial windows. This 2-bedroom,

  Brian Malmquist Compass

  1735 N Paulina St Unit 604, Chicago, IL 60622
• 

  

  /30

  $995,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,839 Sq Ft

  640 W Fullerton Pkwy Unit 3, Chicago, IL 60614

  Perched atop a distinguished vintage building set on a long, deep lot in the perfect East Lincoln Park locale, this extraordinary penthouse residence masterfully blends timeless architectural elegance with a comprehensive designer renovation. Rich in character and meticulously restored, the home showcases an exceptional level of craftsmanship rarely found in today's market. An exquisite home that

  Emily Sachs Wong @properties Christie's International Real Estate

  640 W Fullerton Pkwy Unit 3, Chicago, IL 60614
• 

  

  /59

  $1,865,000

  Pending

  • 3 Beds
  • 3.5 Baths
  • 3,500 Sq Ft

  2600 N Lakeview Ave Unit 9B, Chicago, IL 60614

  From the moment you enter The Marlborough's beautifully restored lobby, this rarely available top-floor 3,500+ sq. ft. southeast corner penthouse sets an elevated tone. Designed in 1912 by Chicago architect Robert DeGoyler, The Marlborough is a classic Beaux-Arts building overlooking Lincoln Park and the lake-offering a rare "New York Central Park" feel in the heart of the city. Private

  Deborah Ballis Compass

  2600 N Lakeview Ave Unit 9B, Chicago, IL 60614
• 

  

  /20

  $410,000

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,850 Sq Ft

  4245 S Langley Ave Unit 3, Chicago, IL 60653

  Welcome to this stunning, sun-drenched penthouse condo nestled in the heart of Bronzeville where modern design meets everyday comfort. This beautifully maintained 3-bedroom, 2-bath residence offers a private entrance, setting the tone for an elevated living experience from the moment you arrive. Step into a spacious, open-concept living area featuring rich dark oak flooring, an elegant electric

  Kayshonna Straughter Blue Door Dave Inc

  4245 S Langley Ave Unit 3, Chicago, IL 60653
• 

  

  /36

  $2,995,000

  Pending

  • 3 Beds
  • 3.5 Baths
  • 3,430 Sq Ft

  416 W Deming Place Unit 4, Chicago, IL 60614

  Step into this one-of-a-kind East Lincoln Park penthouse, expertly designed by luxury lifestyle design group Soucie Horner, flooded with an abundance of natural light with custom features throughout. The open floor plan is not only an example of good design, but allows for high quality day-to-day living. Stepping through the private entrance expect to discover walls of glass/brick/stone, custom

  Jeffrey Lowe Compass

  416 W Deming Place Unit 4, Chicago, IL 60614
• 

  

  /29

  $475,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,700 Sq Ft

  5125 N Kenmore Ave Unit PH-North-5N, Chicago, IL 60640

  Welcome to 5125 North Kenmore, Penthouse North. This rare, expansive two-bedroom, two-bath all-brick penthouse near Lake Michigan and Foster Beach offers unparalleled natural light, with bright treetop views reminiscent of a serene treehouse in the sky. Featuring a chef's kitchen, hardwood floors, front and rear balconies, and an exclusive private rooftop, it's a unique opportunity. With in-unit

  Steve Genyk Baird & Warner

  5125 N Kenmore Ave Unit PH-North-5N, Chicago, IL 60640
• 

  

  /40

  $390,000

  • 2 Beds
  • 2 Baths
  • 1,047 Sq Ft

  235 W Van Buren St Unit 4516, Chicago, IL 60607

  Penthouse level North facing, floor to ceiling windows 2BA/2BD unit with Hardwood floors & white Berber carpeted bedrooms. Both BDRMS are enclosed, 2nd BD has glass partition for privacy. High End Kitchen features SS appl, granite countertop & breakfast bar w/concrete details, lg foyer/office alcove w/lg hall closet; Primary bedroom has floor to ceiling window with double sink vanity and tub

  Michelle Quan Coldwell Banker Realty

  235 W Van Buren St Unit 4516, Chicago, IL 60607
• 

  

  /29

  $1,845,000

  $50K PRICE DROP

  • 2 Beds
  • 3 Baths
  • 2,714 Sq Ft

  450 E Waterside Dr Unit 3409, Chicago, IL 60601

  Iconic views! Penthouse with 14 foot ceilings and full floor to ceiling windows with the most amazing the city has to offer! Stunning views of the Chicago River, lake Michigan and beautiful skyrises light up the night sky. The views will capture you both day and night. Property features 2 balconies and 2 gas fireplaces and a gas line for grilling. Spacious chefs kitchen with barrel vaulted

  Meg Whitted Baird & Warner Fox Valley - Geneva

  450 E Waterside Dr Unit 3409, Chicago, IL 60601
• 

  

  /21

  $700,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,550 Sq Ft

  1536 W Walton St Unit 3, Chicago, IL 60642

  Welcome home! Top-floor two-bedroom, two-bath condo in a modern-construction, three-unit building. Amazing Chicago skyline views and top-tier walkability make this a city dweller's dream. Light and bright, this penthouse home features tall ceilings and three exclusive outdoor spaces, including a full-floor roof deck. Modern finishes and luxury amenities include a built-in Wolf espresso maker,

  Ryan Gossett Compass

  1536 W Walton St Unit 3, Chicago, IL 60642
• 

  

  /41

  $849,000

  $26K PRICE DROP Pending

  • 2 Beds
  • 2 Baths
  • 2,026 Sq Ft

  501 N Wells St Unit 3, Chicago, IL 60654

  Looking for unique? This rarely available 2000+ sq ft duplex-up penthouse with a PRIVATE ROOF TERRACE in the heart of River North is anything but cookie cutter. Set in a boutique 1907 building, this 2 bed, 2 bath home blends vintage character, authentic loft charm, soaring ceilings, oversized windows, and skylights to provide warmth & great natural light throughout. Work from home with incredible

  Mark Placek Coldwell Banker Real Estate Group

  501 N Wells St Unit 3, Chicago, IL 60654
• 

  

  /12

  $420,000

  Pending

  • 2 Beds
  • 1 Bath
  • 963 Sq Ft

  343 W Old Town Ct Unit 705, Chicago, IL 60610

  Tucked away on a quiet brick-paved cul-de-sac in the heart of Old Town, this penthouse-level residence has been thoughtfully updated for contemporary living. The north-facing interior features tall ceilings and floor-to-ceiling windows that provide peaceful treetop views and a bright, airy atmosphere. KEY INTERIOR HIGHLIGHTS - Renovated Kitchen: Outfitted with brand-new appliances and streamlined

  AGNES DONNADIEU Kale Realty

  343 W Old Town Ct Unit 705, Chicago, IL 60610
• 

  

  /18

  $469,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  720 N Larrabee St Unit 1710, Chicago, IL 60654

  Stunning west-facing penthouse loft in the heart of River North offering the perfect blend of updated finishes, turnkey living and unbeatable city views! This move-in ready 2-bedroom, 2-bathroom home features an open-concept floor plan with soaring 11' ceilings, dramatic floor-to-ceiling windows, dark hardwood flooring, custom marble surround gas fireplace, built-in white bookshelf and incredible

  Elena Theodoros-Tamillo @properties Christie's International Real Estate

  720 N Larrabee St Unit 1710, Chicago, IL 60654
• 

  

  /20

  $340,000

  • 3 Beds
  • 2.5 Baths
  • 1,411 Sq Ft

  5252 S Drexel Ave Unit 52521A, Chicago, IL 60615

  Beautiful duplex condominium offering 3 bedrooms and 2.5 bathrooms in the heart of Hyde Park. This thoughtfully designed home features an open-concept living, dining, and kitchen area, creating a spacious and functional layout with abundant natural light from south- and east-facing windows. The main level includes a generously sized primary suite with ample closet space and a large en-suite bath

  Colleen Berg Berg Properties

  5252 S Drexel Ave Unit 52521A, Chicago, IL 60615
• 

  

  /9

  $1,300,000

  New Construction

  • 3 Beds
  • 2.5 Baths

  2072 N Western Ave Unit PH-401, Chicago, IL 60647

  Experience the pinnacle of modern luxury at THE ASH BUCKTOWN, one of the neighborhood's most exciting new developments. ***2 Indoor Heated Electric Car Ready Parking Spaces Included***This meticulously designed 3-bedroom + Office, 2.5-bath penthouse offers stunning, unobstructed Chicago skyline views directly from the main living space. Built with a focus on privacy and performance, the entire

  Roman Popovych Prodan Realty Inc

  2072 N Western Ave Unit PH-401, Chicago, IL 60647
• 

  

  /25

  $285,000

  $4K PRICE DROP Pending

  • 1 Bed
  • 1 Bath
  • 825 Sq Ft

  1910 S Indiana Ave Unit 727, Chicago, IL 60616

  MOTIVATED SELLER! This bright, stylish penthouse in the historic 'Bank Note Place' of South Loop's coveted Prairie District offers incredible city and lake views. The northwest corner unit features an open living and dining space with, hardwood floors, tons of natural light and a large balcony to soak in the scenery. Freshly painted, it showcases finished ceilings with exposed ductwork. The

  Patricia Konrath @properties Christie's International Real Estate

  1910 S Indiana Ave Unit 727, Chicago, IL 60616
• 

  

  /65

  $7,500,000

  • 4 Beds
  • 4.5 Baths
  • 5,734 Sq Ft

  363 E Wacker Dr Unit 9101, Chicago, IL 60601

  OWN THE ENTIRE 91ST FLOOR OF THE ST. REGIS CHICAGO! The highest customizable residence in Chicago and the Midwest and the only home in the building offering complete design freedom. Perched atop the iconic St. Regis Chicago, this extraordinary full-floor penthouse presents a once-in-a-lifetime opportunity to create a completely bespoke home in the sky. Spanning the entire 91st floor, this

  Laura England Compass

  363 E Wacker Dr Unit 9101, Chicago, IL 60601
• 

  

  /35

  $1,495,000

  • 3 Beds
  • 2.5 Baths
  • 2,450 Sq Ft

  1230 N State Pkwy Unit 28A, Chicago, IL 60610

  Location, Lifestyle, and Lake View! This rarely available half floor Gold Coast penthouse has it all. Originally two units combined into one expansive residence, this one of a kind home offers approx. 2450 square feet with floor to ceiling windows, wraparound east, south and west exposures showcasing Lake Michigan, the city's skyline and stunning sunset views. Fully renovated several years ago,

  Mark Placek Coldwell Banker Real Estate Group

  1230 N State Pkwy Unit 28A, Chicago, IL 60610
• 

  

  /30

  $275,000

  • 1 Bed
  • 1 Bath
  • 832 Sq Ft

  320 E 21st St Unit 807, Chicago, IL 60616

  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

  Lindsey Richardson Baird & Warner

  320 E 21st St Unit 807, Chicago, IL 60616
• 

  

  /19

  $845,000

  • 2 Beds
  • 2 Baths
  • 1,185 Sq Ft

  600 N Fairbanks Ct Unit 3307, Chicago, IL 60611

  This is the one buyers wait for-and miss if they hesitate. A rare southwest corner condo at 600 N Fairbanks Ct #3307 just hit the market, and the views alone are worth a visit. Floor-to-ceiling windows wrap the entire space, flooding it with light and delivering sweeping panoramic city views you won't get from most units. Step out onto your private balcony and you'll understand why this corner

  Jeffrey Sklar Beycome Brokerage Realty LLC

  600 N Fairbanks Ct Unit 3307, Chicago, IL 60611
• 

  

  /21

  $315,000

  Pending

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft

  3150 N Sheffield Ave Unit 606, Chicago, IL 60657

  Stunning corner penthouse with sweeping city views and soaring 14-ft ceilings in a historic concrete loft building. Perfectly positioned in the heart of Lakeview, just steps to the lake, the el, top-rated restaurants, nightlife, and shopping. This light-filled unit features hardwood floors throughout, a contemporary kitchen with stainless steel appliances and quartz countertops. Enjoy casual

  Peter Fisk Compass

  3150 N Sheffield Ave Unit 606, Chicago, IL 60657
• 

  

  /17

  $265,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft

  801 S Plymouth Ct Unit 1111, Chicago, IL 60605

  Rarely available Penthouse unit overlooking Sears Tower (Willis) and downtown Chicago. 2 large bedrooms, master has large walk-in closet and private full bath.The building features door staff, laundry room, storage lockers, bike storage, package receiving room, party room and on-site management office.located steps from the CTA Red Line, with easy access to Target, Jewel, Trader Joe's, Whole

  Qian Kun Chen Kale Realty

  801 S Plymouth Ct Unit 1111, Chicago, IL 60605

Showing Results 321 - 355, Page 9 of 9