Penthouses for Sale in Chicago, IL

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  /29

  $675,000 Open Wed 4:30PM - 6PM

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

  1548 N Hoyne Ave Unit 3, Chicago, IL 60622

  Best of both Bucktown and Wicker Park near 6 corners! This stunning penthouse delivers the perfect blend of luxury, light, and location-complete with a rare private 2-car garage and an expansive 20' x 20' private roof deck, ideal for entertaining. Flooded with natural light from a dramatic new skylight (2025) and desirable east/west exposure, the home showcases beautiful skyline views and an

  Guido Piunti @properties Christie's International Real Estate

  1548 N Hoyne Ave Unit 3, Chicago, IL 60622
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  /24

  $299,900

  • 1 Bed
  • 1 Bath

  1221 N Dearborn St Unit PH8S, Chicago, IL 60610

  At the top of one of the Gold Coast's most established buildings, Penthouse 8 South at 1221 N Dearborn delivers space, light, and timeless city appeal. Natural light moves easily through the condo, complemented by a beautiful view of Lake Michigan. The layout is unique and spacious, featuring a large lofted bedroom, excellent storage, and a sense of separation that enhances both comfort and

  Jackie Manrique Jameson Sotheby's Intl Realty

  1221 N Dearborn St Unit PH8S, Chicago, IL 60610
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  /29

  $1,000,000

  • 3 Beds
  • 4 Baths
  • 2,300 Sq Ft

  635 N Dearborn St Unit 2803, Chicago, IL 60654

  Stunning Two Story Penthouse With Floor to Ceiling Windows and Panoramic Views at The Caravel in the Heart of River North. Master and Second Bedrooms Are Both En Suite Upper Floor Den or Third Bed Room with half bath. Walk out to the Spectacular Private Terrace, over 700 sq ft of Teak Decking, Enjoy the North, South, and East Views. This Home is Perfect for Entertaining All Year Round. Additional

  Frank Paganis, CCIM Coldwell Banker Real Estate Group

  635 N Dearborn St Unit 2803, Chicago, IL 60654
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  /37

  $799,000

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

  700 W Van Buren St Unit PH2, Chicago, IL 60607

  INCREDIBLE newly renovated concrete DUPLEX LOFT PENTHOUSE with an oversized PRIVATE BALCONY with BREATHTAKING SKYLINE VIEWS in the heart of West Loop! This INSANELY gorgeous 2 bed + office/ 2.1 bath home features extraordinarily high ceilings, city views from every room, extra-large floor to ceiling windows, desired open kitchen/living room/dining room, separate office area (currently being used

  Azin Amiran Jameson Sotheby's Intl Realty

  700 W Van Buren St Unit PH2, Chicago, IL 60607
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  /32

  $369,000

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

  2665 W Warren Blvd Unit 3, Chicago, IL 60612

  Penthouse Perfection in the Heart of Chicago! Experience sophisticated city living in this exceptionally designed 3-bedroom, 2-bath top-floor unit featuring vaulted ceilings, skylights, and hardwood floors throughout. The modern kitchen boasts brand-new glass-finish appliances, sleek granite countertops, and an open floor plan that flows seamlessly into the bright living area with a Juliet

  Konstantin Shelegeda Inter Properties Inc

  2665 W Warren Blvd Unit 3, Chicago, IL 60612
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  /33

  $12,250,000

  • 6 Beds
  • 6.5 Baths
  • 9,250 Sq Ft

  800 N Michigan Ave Unit 67, Chicago, IL 60611

  The last raw penthouse available in the Gold Coast! An amazing opportunity to transform this true duplex Penthouse at Chicago's esteemed Park Hyatt. Offering the absolute best combination of 360-degree Lake Michigan and City skyline views, 12-foot ceilings, 5-Star Hotel amenities, 700sf of private outdoor space atop the duplex, NoMi Club, and access to the best shopping and dining the Gold Coast

  Susan Miner Premier Relocation, Inc.

  800 N Michigan Ave Unit 67, Chicago, IL 60611
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  /5

  $769,500 Open Sat 11AM - 12:30PM

  • 3 Beds
  • 2.5 Baths
  • 2,300 Sq Ft

  6216 S Woodlawn Ave Unit A, Chicago, IL 60637

  Ultra-contemporary new construction corner residences within a gated 14-home community, designed to elevate daily living while maintaining effortless sophistication. These striking homes feature heated floors-polished concrete or engineered white oak-solid-core flat-panel doors, LED lighting, tall ceilings, and an attached two-car garage. The dramatic two-story main level is anchored by a

  Michelle Browne @properties Christie's International Real Estate

  6216 S Woodlawn Ave Unit A, Chicago, IL 60637
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  /16

  $1,599,000 New Construction

  • 4 Beds
  • 2.5 Baths

  1511 W Roscoe St Unit PH, Chicago, IL 60657

  Exquisite, new construction, duplex-up penthouse designed by Studio Group delivering this July. This home offers a refined blend of modern luxury and timeless craftsmanship on one of the Southport Corridor's most desirable tree-lined streets. The residence features four bedrooms, two-and-a-half baths, two spacious family rooms, and a private rooftop deck, thoughtfully designed for both everyday

  Michael Yeagle @properties Christie's International Real Estate

  1511 W Roscoe St Unit PH, Chicago, IL 60657
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  /11

  $295,000

  • 2 Beds
  • 2 Baths
  • 1,525 Sq Ft

  6933 N Kedzie Ave Unit 1209, Chicago, IL 60645

  Welcome to Winstone Tower "Deluxe Penthouse" the most sought about location in the building. Experience the panoramic and fantastic view of Evanston, Skokie and Chicago Skyline and the colorful sunrise view. This 2-bedroom 2 bathroom was completely renovated in 2023 highlighting open layout, gleaming engineered hardwood flooring throughout except the kitchen with beautiful porcelain tile flooring

  Tito Pasia Net 1 Real Estate, Corp.

  6933 N Kedzie Ave Unit 1209, Chicago, IL 60645
• 

  

  /22

  $1,299,000

  • 4 Beds
  • 2.5 Baths
  • 3,100 Sq Ft

  1412 W Diversey Pkwy Unit B, Chicago, IL 60614

  This remarkable 5,500 sq ft, two-unit condo building in Lincoln Park, situated at the corner of Diversey and Southport, offers size, flexibility, and an unbeatable location. The 3,100 sq ft penthouse triplex stands out with dramatic cathedral ceilings, hardwood flooring, and a classic woodburning fireplace. Its defining highlight is the private outdoor escape, designed for both quiet moments and

  Thalia Mena Coldwell Banker Realty

  1412 W Diversey Pkwy Unit B, Chicago, IL 60614
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  /30

  $440,000

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft

  1400 N State Pkwy Unit 18A, Chicago, IL 60610

  This highly sought after & rarely available PENTHOUSE 2 bedroom, 2 bathroom corner unit in the heart of the Gold Coast is a must see! Perched above the treetops with sweeping lake, skyline, and sunset views, this beautifully renovated residence captures the very best of Chicago from every angle. The open living and dining area flows seamlessly into a stylish kitchen featuring quartz countertops,

  Kelsey Shaw @properties Christie's International Real Estate

  1400 N State Pkwy Unit 18A, Chicago, IL 60610
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  /35

  $780,000

  • 3 Beds
  • 2 Baths
  • 2,540 Sq Ft

  161 W Harrison St Unit 1208, Chicago, IL 60605

  A Penthouse like no other in Printers Row. For the buyer who craves something truly extraordinary - this spectacular 2,600 sq. ft. corner penthouse loft in the heart of the South Loop delivers soaring style, dramatic light, and unforgettable city views. With 15-foot ceilings, an uninterrupted 50 feet of east-facing windows, and a one-of-a-kind vaulted 20' skylight, the skyline becomes your daily

  Stephanie Kramer @properties Christie's International Real Estate

  161 W Harrison St Unit 1208, Chicago, IL 60605
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  /32

  $5,900,000

  • 5 Beds
  • 6 Baths
  • 8,400 Sq Ft

  800 N Michigan Ave Unit 63, Chicago, IL 60611

  Unparalleled opportunity to own a full floor Park Tower penthouse at a truly outstanding value. Spanning 8,400 square feet, this residence offers 360-degree views of Chicago's iconic skyline, world-class architecture, and Lake Michigan, delivering front-row sunrise to sunset views. Perched above the Park Hyatt Hotel, this 5-bedroom, 4.2-bath home provides access to top-tier amenities: Spa, Indoor

  Jeffrey Lowe Compass

  800 N Michigan Ave Unit 63, Chicago, IL 60611
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  /22

  $349,900

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

  4415 N Troy St Unit 44153, Chicago, IL 60625

  AMAZING TOP FLOOR PENTHOUSE UNIT W/BALCONY OFF LIVING ROOM !! FINISHES INCLUDE WIDE PLANK HARDWOOD FLOORS, SS APPLIANCES (WITH RECENT UPGRADES), GRANITE COUNTERS, OVERSIZED ISLAND, IN-UNIT LAUNDRY, MASTER BATH (RECENTLY REMODELED). ADDITIONAL SUN ROOM AREA OFF LIVING SPACE. FEATURES CENTRAL AIR AND AMPLE STORAGE. EASY ACCESS TO CTA BROWN LINE, CLOSE TO OTHER TRANSPORTATION, RAVENSWOOD MANOR AND

  Elzbieta Zubek Chicagoland Brokers Inc.

  4415 N Troy St Unit 44153, Chicago, IL 60625
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  /20

  $269,000

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft

  1460 N Sandburg Terrace Unit 2904A, Chicago, IL 60610

  Penthouse with million dollar views !! 2025 Complete Rehab. Bright Jr 1 bedroom features hardwood floors throughout. Updated kitchen and bath. Closet space galore! Enjoy living in Sandburg Village. Building has a rooftop deck. Workout room, two community pools and tennis/pickleball courts are available. Walk to everything location. Shops, groceries, entertainment, dining and the North Ave beach

  Kimberly Saydak Baird & Warner

  1460 N Sandburg Terrace Unit 2904A, Chicago, IL 60610
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  /35

  $399,999

  • 2 Beds
  • 2 Baths
  • 1,216 Sq Ft

  1070 W 15th St Unit 404, Chicago, IL 60608

  Discover this exceptional 2-bedroom, 2-bathroom penthouse condo with a bonus den/office, situated atop a historic loft building. This newer construction residence presents in pristine condition, featuring dark-stained hardwood floors, professional modern neutral paint, and freshly cleaned carpets. The highly desirable split floor plan ensures privacy with fully enclosed bedrooms. The gourmet

  Cory Tanzer Option Premier LLC

  1070 W 15th St Unit 404, Chicago, IL 60608
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  /31

  $399,000

  • 2 Beds
  • 1 Bath

  1560 N Sandburg Terrace Unit 4011J, Chicago, IL 60610

  An outstanding value for this fully renovated high-floor 2BR / 1BA condo. Perched on the 40th floor, this stunning property offers unobstructed skyline & sunset views from a west-facing balcony. Wide-plank white oak floors flow throughout the smart open layout, leading to a sleek kitchen with quartz countertops, custom white cabinetry, island seating & stainless-steel appliances. The large

  Jennifer Furlong Perrin @properties Christie's International Real Estate

  1560 N Sandburg Terrace Unit 4011J, Chicago, IL 60610
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  /16

  $195,000

  • 2 Beds
  • 2 Baths
  • 825 Sq Ft

  6730 S South Shore Dr Unit 1604, Chicago, IL 60649

  Awesome Penthouse Suite here at 6730 S. South Shore Dr. Overlooking the New Obama Library, Lake Michigan views and Downtown views! Across the street from the Golf Course and Lakefront, and nearby Museum of science and industry and South shore country club. The unit included its own gated outdoor parking space. With 2 Large bedrooms and 2 full baths, updated kitchen and entire unit just

  Michael Giliano Compass

  6730 S South Shore Dr Unit 1604, Chicago, IL 60649
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  /53

  $1,800,000

  • 5 Beds
  • 3.5 Baths
  • 4,200 Sq Ft

  2456 W Ohio St, Chicago, IL 60612

  Architecturally stunning corner home in a 4-residence development by a leading Chicago builder, offering striking design, first-class finishes, and an exceptional level of detail throughout. The open-concept floor plan features soaring 11-foot ceilings, expansive windows overlooking Smith Park, and a dramatic open glass staircase that floods the interior with natural light. At the heart of the

  Grigory Pekarsky Vesta Preferred LLC

  2456 W Ohio St, Chicago, IL 60612
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  /20

  $250,000 Open Fri 4PM - 6PM

  • 1 Bed
  • 1 Bath
  • 950 Sq Ft

  1550 S Indiana Ave Unit 401, Chicago, IL 60605

  Set in the historic Penthouse Lofts in the Prairie District, this striking east-facing 1-bedroom, 1-bath loft offers 950 square feet of dramatic, light-filled living with standout views of Soldier Field and a glimpse of the lake. Soaring 14-foot ceilings, oversized windows, and a private balcony create an airy, elevated feel, while the open layout is ideal for both everyday living and

  John O'Connor Top Care Realty LLC

  1550 S Indiana Ave Unit 401, Chicago, IL 60605
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  /33

  $865,000

  • 3 Beds
  • 2.5 Baths
  • 2,144 Sq Ft

  321 N Jefferson St Unit P3211, Chicago, IL 60661

  Experience unparalleled luxury in this unbelievable 3-bedroom plus den, 2.1-bath duplex-up penthouse in an exceptional Fulton Market / West Loop location. Tucked within a boutique condo building on a quieter street, this sun-drenched residence offers a beautifully designed open-concept floor plan ideal for entertaining now elevated with a complete kitchen renovation, living room redesign, all new

  Natalie Renna Compass

  321 N Jefferson St Unit P3211, Chicago, IL 60661
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  /39

  $3,250,000

  • 5 Beds
  • 7 Baths
  • 5,700 Sq Ft

  1842 N Wolcott Ave, Chicago, IL 60622

  A masterful expression of contemporary design, this all-brick Environs residence sits on a wide 30' lot along one of Bucktown's most coveted blocks. Unique features include a dramatic two-story foyer, 5-inch quartersawn maple floors, custom railing sets, and a sun-filled living room with a fireplace. The contemporary kitchen features custom anegre cabinetry, a 48" Sub-Zero refrigerator, Dacor

  Jacqueline Lafferty Baird & Warner

  1842 N Wolcott Ave, Chicago, IL 60622
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  /28

  $1,399,000 Open Sat 12PM - 2PM

  • 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
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  /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
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  /71

  $2,350,000

  • 3 Beds
  • 4 Baths
  • 5,020 Sq Ft

  333 W Hubbard St Unit 1006, Chicago, IL 60654

  Welcome to the epitome of penthouse living in Chicago's premier River North neighborhood! This impressive home was designed with entertaining in mind with over 10,000 SF of indoor/outdoor living in the heart of the city! Residence 1006 boasts over 5000 SF of interior space, with four balconies off the main living level and a private, 5000 SF award-winning roof deck and garden. From the moment you

  Melanie Giglio-Vakos Compass

  333 W Hubbard St Unit 1006, Chicago, IL 60654
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  /56

  $1,149,000

  • 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
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  /20

  $209,000

  • 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! 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 in place through June 30, 2026-providing immediate rental income with the

  Mita Nermal Shewakramani Mita Shewakramani

  3950 N Lake Shore Dr Unit 2312, Chicago, IL 60613
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  /58

  $4,850,000

  • 4 Beds
  • 4.5 Baths
  • 3,596 Sq Ft

  2350 N Orchard St Unit 701, Chicago, IL 60614

  The first penthouse resale at The Orchard Private Residences, this expansive 4-bedroom, 4.5-bath East Lincoln Park home offers the scale and comfort of a single-family residence with the light, views, and security of full-service condominium living. Occupying the building's premier tier, it features panoramic city and lake views, a large terrace off the main living space, and an extraordinary

  Jennifer Ames Engel & Voelkers Chicago

  2350 N Orchard St Unit 701, Chicago, IL 60614
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  /28

  $449,000

  • 1 Bed
  • 1.5 Baths

  155 N Harbor Dr Unit 5404, Chicago, IL 60601

  Top Floor Penthouse Level - Unit 5404 is a spacious 1 bedroom /1.1 bathroom home located in Lakeshore East at prestigious Harbor Point. With 13 windows throughout, this thoughtful floor-plan is set in the "curve" and provides stunning views of the city, lake and Navy Pier. Unit highlights include a stainless kitchen with generous cabinet/counter space and breakfast bar seating for three, separate

  Liane Pruchnik Berkshire Hathaway HomeServices Chicago

  155 N Harbor Dr Unit 5404, Chicago, IL 60601
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  /32

  $900,000 Open Sun 10:30AM - 12:30PM

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

  1161 W Madison St Unit 4S, Chicago, IL 60607

  Distinctive penthouse loft duplex in an intimate West Loop building, featuring two private outdoor spaces and sweeping city views. Offering approximately 1,700 square feet, this residence includes two assigned exterior parking spaces in the price. Gut renovated in 2017 in collaboration with En Masse Architecture and Design, with all windows replaced during the renovation. The home is filled with

  Carrie McCormick @properties Christie's International Real Estate

  1161 W Madison St Unit 4S, Chicago, IL 60607
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  /40

  $285,000

  • 2 Beds
  • 2 Baths
  • 996 Sq Ft

  1001 W 15th St Unit 241, Chicago, IL 60608

  Fabulous 2-Bed/2-Bath Concrete Loft in Popular University Commons! Expect to be impressed by this sought-after split-bedroom floor plan featuring soaring 12' concrete ceilings, expansive north-facing floor-to-ceiling windows with beautiful treetop views, and generous living spaces. The wide living area includes hardwood floors, a cozy gas fireplace, space for a full-size dining table, and access

  Amanda McMillan @properties Christie's International Real Estate

  1001 W 15th St Unit 241, Chicago, IL 60608
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  /33

  $1,099,900

  • 3 Beds
  • 2.5 Baths
  • 2,400 Sq Ft

  1001 W Madison St Unit 710, Chicago, IL 60607

  Exceptional West Loop corner penthouse -- centrally located to the best of West Loop and walkable to Fulton Market, Downtown, Metra station, and CTA. Easy walk to Bartelme Park and Skinner Park. A 5-block drive to both I90 and I290. Great views of West Loop / downtown from all rooms. Floor-to-ceiling windows allow tons of natural light and highlight the penthouse experience. Remodeled by the

  Steven Katz @properties Christie's International Real Estate

  1001 W Madison St Unit 710, Chicago, IL 60607
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  /2

  $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
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  /73

  $7,999,000 New Construction

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

  363 E Wacker Dr Unit 9101, Chicago, IL 60601

  Perched atop the iconic St. Regis Chicago, this full-floor penthouse is the highest residential customizable home in the city and the Midwest! Spanning the entire 91st floor, this raw space offers a rare chance to create a one-of-a-kind residence tailored entirely to your vision. The ONLY unit in the building that can be fully customized, this offers 360-degree views of Chicago's world-renowned

  Laura England Compass

  363 E Wacker Dr Unit 9101, Chicago, IL 60601
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  /32

  $350,000

  • 1 Bed
  • 1 Bath
  • 942 Sq Ft

  1629 S Prairie Ave Unit 3110, Chicago, IL 60616

  Experience elevated city living in this stunning penthouse residence in the sought-after Prairie District. Perfectly positioned on a quiet street in the South Loop, this beautifully designed condo offers modern finishes, an open floor plan, and breathtaking city and sunset views. Step inside this spacious 1 bed+ den filled with natural light from floor-to-ceiling windows. The contemporary kitchen

  Daryl Ceaser Baird & Warner

  1629 S Prairie Ave Unit 3110, Chicago, IL 60616
• 

  

  /25

  $289,000

  • 1 Bed
  • 1 Bath
  • 825 Sq Ft

  1910 S Indiana Ave Unit 727, Chicago, IL 60616

  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 kitchen, transformed

  Patricia Konrath @properties Christie's International Real Estate

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

  

  /23

  $224,700

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft

  655 W Irving Park Rd Unit 5413, Chicago, IL 60613

  Lively in Lakeview! Spacious penthouse with breathtaking views of Lake Michigan, the iconic Chicago skyline and Wrigley Field. Bask in the sun all day in this south-facing condo as natural light pours in from the oversized windows. The unit features hardwood floors in the main living area. The open kitchen w breakfast bar is adorned with cherry cabinets, granite countertops & stainless steel

  Kim Kerbis @properties Christie's International Real Estate

  655 W Irving Park Rd Unit 5413, Chicago, IL 60613

Showing Results 121 - 157, Page 4 of 4