Chicago Penthouses For Sale

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A penthouse condo in Chicago is a unit that’s typically on the highest floor of a building, giving its owners the best views, and often times, the most luxurious features. The idea of a penthouse was actually crated back in the 1920s when industry and economic growth sparked a massive construction boom in New York City. The demand for living in urban areas was through the roof and some of the most desirable living spaces at the time were at the top of existing buildings, and from there, the penthouse was born. 

Learn more about Chicago penthouses for sale below, or start browsing active penthouse listings on the MLS below:

Search Chicago Penthouses For Sale

All Listings Under $100,000 $100,000 - $200,000
$200,000 - $300,000 $300,000 - $400,000 $400,000 - $500,000
$500,000 - $600,000 $600,000 - $700,000 $700,000 - $800,000
$800,000 - $900,000 $900,000 - $1,000,000 Over $1,000,000
387 Properties Found. Page 1 of 17

One Bennett Park Has Taken Its Place Among Chic...

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$15,170,000 Active

  • 4 Beds
  • 6 Baths
  • 7,582 ft²

Residential

451 East Grand Avenue Ph65, Chicago, IL

MLS® #11063904

One Bennett Park Has Taken Its Place Among Chicago's Most Elite Residences. Designed By Robert A.m. Stern Architects And Developed By Related Midwest, This World Class Building Was Designed From The Top Down. Gracing The Crown Of This Iconic Lakefront Tower, Penthouse 65 Is Being Offered As A Ful...

3 Bedroom Residential Property in Chicago, IL

REDUCED 3% Photo of Listing #10840152
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$8,250,000 Price Change

  • 3 Beds
  • 4 Baths
  • 6,000 ft²

Residential

21 East Huron Street 4501, Chicago, IL

MLS® #10840152

Absolutely Stunning, David Adler Designed Duple...

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$7,999,000 Active

  • 6 Beds
  • 6 Baths
  • 7,900 ft²

Residential

1325 North Astor Street 13, Chicago, IL

MLS® #10509929

Absolutely Stunning, David Adler Designed Duplex Penthouse Set Atop One Of The Finest, Vintage Condominium Buildings On Astor Street. Available For The First Time In Nearly 50 Years, This 6 Bedroom Home Boasts Nearly 8000 Square Feet And Features 3 Separate Private Terraces With Amazing City And ...

Absolute Elegance Throughout! 199 E Lakeshore D...

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$7,990,000 Active

  • 4 Beds
  • 7 Baths
  • 9,672 ft²

Residential

199 East Lake Shore Drive 10-11e, Chicago, IL

MLS® #10881522

Absolute Elegance Throughout! 199 E Lakeshore Drive Is One Of The Premiere Luxury Buildings On The Magnificent East Lake Shore Drive, Originally Designed By Benjamin Marshall And Reimagined As A Fabulous Co Op Building. This Unbelievable Penthouse Combines The East Side Of Both The 10th And The 1...

This Remarkable, Architecturally Significant, A...

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$6,750,000 Active

  • 3 Beds
  • 4 Baths
  • 4,250 ft²

Residential

2550 North Lakeview Avenue S3802, Chicago, IL

MLS® #11048245

This Remarkable, Architecturally Significant, Aia Award Winning Designed Home Offers The Rare Opportunity To Live In One Of Only Two Penthouses In The Prestigious Lp2550. This Magnificent Home Features 12-foot Ceilings And Exquisite Details Including Dramatic Arched Windows And Doors. 4250ft Of C...

5 Bedroom Residential Property in Chicago, IL

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$4,995,000 Active

  • 5 Beds
  • 6 Baths
  • 5,913 ft²

Residential

1300 North State Parkway 1202, Chicago, IL

MLS® #10968350

Glorious Duplex Home, Atop The Four Seasons Hot...

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$4,950,000 Active

  • 3 Beds
  • 6 Baths
  • 7,000 ft²

Residential

132 East Delaware Place 6302, Chicago, IL

MLS® #10849608

Glorious Duplex Home, Atop The Four Seasons Hotel + 900 North Michigan Avenue Shops, Boasting 4 Bedrooms, Multiple Office Spaces ( Easily Affording More Bedrooms), And A Home Theater Spanning Over 7000 Square Feet. Bathed In The Ever-changing Dramatic Light Of The Lake And City, This Residence Co...

Located On The 70th Floor Of Lake Point Tower, ...

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$4,700,000 Active

  • 4 Beds
  • 5 Baths
  • 4,700 ft²

Residential

505 North Lake Shore Drive 7000, Chicago, IL

MLS® #10954752

Located On The 70th Floor Of Lake Point Tower, It Is The Most Sought-after Rooftop Location In Downtown Chicago. With Spectacular 360-degree Panoramic Views Of The Chicago's Skyline, Lake Michigan, The Chicago Harbor And Millennium Park.bring Your Architect And Imagination And Make This One Of A ...

Spectacular Opportunity For A Full-floor Luxuri...

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$4,100,000 Active

  • 4 Beds
  • 5 Baths
  • 5,500 ft²

Residential

21 East Huron Street 4701, Chicago, IL

MLS® #11003796

Spectacular Opportunity For A Full-floor Luxurious Residence At The Pinnacle! Offering Over 5500 Square Feet Of Single Level Living, Panoramic City Views And Outstanding Outdoor Space. Perfect For Entertaining, The Expansive Living And Dining Rooms With Lake And City Views Offer Multiple Spaces T...

10,000 Sq. Ft Indoor/outdoor True Penthouse In ...

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$3,900,000 Active

  • 3 Beds
  • 4 Baths
  • 5,020 ft²

Residential

333 West Hubbard Street 1006, Chicago, IL

MLS® #11066238

10,000 Sq. Ft Indoor/outdoor True Penthouse In Heart Of River North. Step From Your Premier 1st Floor Parking Spaces Directly Into The Doorman Lobby And Up To Your 10th Floor Penthouse. 5000 Sq Ft Inside, 11 Ft Ceilings, 4 Balconies, 3 Wood-burning Fireplaces (a True Rarity Downtown), And Anoth...

Staged Photos Added For Your Convenience. Fabu...

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$3,495,000 Active

  • 4 Beds
  • 5 Baths
  • 7,100 ft²

Residential

25 East Superior Street 4801, Chicago, IL

MLS® #10977882

Staged Photos Added For Your Convenience. Fabulous Entire 48th Floor At The Fordham. Taxes Under Separate Appeal And Expected To Be Lowered To ~$60k. **please See Letter From Tax Lawyer Under Documents Tab.** Approximately 7,100sf Interior Plus Two Large Terraces. Access Via Private Penthouse Lo...

Rare Open Raw Space Penthouse. This Jaw Droppin...

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$3,250,000 Active

  • 3 Beds
  • 4 Baths
  • 3,300 ft²

Residential

65 East Goethe 8w, Chicago, IL

MLS® #10603295

Rare Open Raw Space Penthouse. This Jaw Dropping Gold Coast Opportunity Is Located At Prestigious 65 East Goethe. Approximately 3300 Total Sq Ft Of Residential Interior Living, Plus 2 Additional Patios (east/ West Facing).one Level Up Is Your Private 1500 Sq Ft Roof Top Terrace (4 Direction Expos...

Last Unit At The Brooklyn Chicago Designed By A...

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$3,195,000 Contingent

  • 4 Beds
  • 5 Baths

Residential

351 West Huron Street 7, Chicago, IL

MLS® #10968303

Last Unit At The Brooklyn Chicago Designed By Award Winning Architect Hartshorne Plunkard In A Prime River North Location. This Penthouse With Amazing Views, Features Private Outdoor Terrace And Full Floor Luxury. Living Space Thoughtfully Designed With A Split Floorplan Featuring 4-bedrooms, 4.5...

Stunning Penthouse In Quaint Vintage Building O...

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$3,100,000 Active

  • 3 Beds
  • 4 Baths
  • 3,094 ft²

Residential

33 East Bellevue Place E7, Chicago, IL

MLS® #11039728

Stunning Penthouse In Quaint Vintage Building On Bellevue. Two Large Outdoor Terraces. Duplex Feels Like A Town Home On Top Of The Building. One Indoor Parking Space Is Included. Great Lake Views Off The Main Terrace Facing East. Recent Renovations Make This A Show Stopper. It Is Easy To Sho...

A Very Rare Find: Absolutely Stunning Half-flo...

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$3,100,000 Active

  • 3 Beds
  • 4 Baths

Residential

1550 North State Parkway 1001, Chicago, IL

MLS® #10817168

A Very Rare Find: Absolutely Stunning Half-floor Penthouse In Benjamin Marshall's Dazzling Beaux Arts 1550 State Pkwy. This Exquisite 3,200 Sq. Ft. Home Boasts Perfection In Every Room, With Uninterrupted Views Of The Lake, Beach, Lincoln Park, And The Historic Mansions Of The Gold Coast. Rece...

Exceptional Full-floor Penthouse On South Michi...

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$2,950,000 Active

  • 4 Beds
  • 5 Baths
  • 6,000 ft²

Residential

888 South Michigan Avenue Ph2, Chicago, IL

MLS® #11033451

Exceptional Full-floor Penthouse On South Michigan Ave Cultural Mile Offers Breathtaking Panoramic Views Of Chicago Lakefront, "forever Open, Clear And Free." Step Off The Keyed Elevator Into Your Spacious Private Center Foyer And Into An Executive Home Office Suite. To The East Is A Stunningly E...

Chic And Stylish Designer Curated Half Floor Pe...

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$2,850,000 Active

  • 3 Beds
  • 3 Baths
  • 3,700 ft²

Residential

25 East Superior Street 4402, Chicago, IL

MLS® #11036753

Chic And Stylish Designer Curated Half Floor Penthouse In The Fordham. This One Of A Kind Penthouse Offers Bespoke Finishes Throughout With No Detail Overlooked. This Luxurious Condo Is An Entertainer's Dream With Multiple Living Rooms (one Featuring A Fireplace), Massive Dining Room Off The Kitc...

Absolutely Stunning One-of-a-kind Penthouse Wit...

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$2,795,000 Active

  • 4 Beds
  • 5 Baths
  • 4,200 ft²

Residential

190 East Walton Street 701, Chicago, IL

MLS® #11033913

Absolutely Stunning One-of-a-kind Penthouse With 1800 S.f. Private Roof Deck Plus Terrace & Grill Deck Off Family Room. Fantastic 4200 Sq. Ft. Floor Plan With Gracious Formal Living Room And Dining Room Plus An Extra Family Room Off Of Kitchen. Deep Bay Windows Adorn This Unit Adding To Its Cozy...

As Featured In Crain's, This Newly Renovated Pe...

REDUCED 27% Photo of Listing #11078797
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$2,739,000 Active

  • 4 Beds
  • 6 Baths
  • 4,100 ft²

Residential

1340 North State Parkway 4s, Chicago, IL

MLS® #11078797

As Featured In Crain's, This Newly Renovated Penthouse In The Former Playboy Mansion Offers 4,100 Sqft Of Fresh Contemporary Living Space Plus A South-facing Terrace And Attached Garage Parking. Highlights Include Generous Space To Entertain, A Stunning New Kitchen, Four Large Bedrooms With Beaut...

3 Bedroom Residential Property in Chicago, IL

REDUCED 2% Photo of Listing #11044871
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$2,690,000 Active

  • 3 Beds
  • 4 Baths
  • 4,500 ft²

Residential

1152 West Fulton Market Street 5c, Chicago, IL

MLS® #11044871

A Very Special Penthouse Available At The Aqua ...

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$2,500,000 Active

  • 2 Beds
  • 3 Baths
  • 1,807 ft²

Residential

225 North Columbus Drive 8106, Chicago, IL

MLS® #10985904

A Very Special Penthouse Available At The Aqua Tower Condominiums. Corner Unit Facing Southeast. Unit Features 16' Floor To Ceiling Glass Windows. Open Floor Plan. Custom Kitchen. Automated Drapes And Blackout Shades. Master Suite With Spa And A Dressing Room. Second Bedroom Features Custom Buil...

Bring Your Clients To This Most Unique Penthous...

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$2,500,000 Active

  • 5 Beds
  • 4 Baths
  • 3,600 ft²

Residential

505 North Lake Shore Drive 6702, Chicago, IL

MLS® #10646527

Bring Your Clients To This Most Unique Penthouse And Behold The Glorious Views Of Lake, City, Navy Pier, River, Beach, Boats, Park, Sunrise, Sunsets & More, Only This Grand Property Can Offer. This 67th Floor Penthouse Of A Gem Shows Chicago From The Unique Lake Point Tower - The Only Building E...

Crowning The Top Two Floors On The Best Promont...

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$2,350,000 Active

  • 4 Beds
  • 4 Baths
  • 3,659 ft²

Residential

33 West Ontario Street Ph-d, Chicago, IL

MLS® #11056911

Crowning The Top Two Floors On The Best Promontory In Chicago With Absolute Privacy And Expansive Views, Sits An Incredibly Elegant And Exquisitely Designed Home In The Sky - Penthouse D. Perched Over 600 Feet In The Air With Absolutely Breathtaking 180-degree Views Of Lake Michigan, Downtown, An...

One Of A Kind Duplex Penthouse In The Heart Of ...

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$2,245,000 Active

  • 3 Beds
  • 3 Baths
  • 3,500 ft²

Residential

33 East Bellevue Place Ph-w7, Chicago, IL

MLS® #11052233

One Of A Kind Duplex Penthouse In The Heart Of The Gold Coast. Spectacular Views From The 800+ Ft Outdoor Space On Both Levels - Front Terrace And Rear Deck. This Beautiful Residence Includes 3 Bedrooms Plus A Family Room, A Beautiful Gourmet Eat-in Kitchen With A Butler's Pantry, A Grand Master ...

 

Search Downtown Chicago Penthouses By Neighborhood 

Downtown Chicago is where you’ll find many of Chicago’s most spectacular and most luxurious penthouse condos for sale. Situated high above the bustling city streets, most high-rise penthouses in Chicago offer sprawling views of the downtown landscape and Lake Michigan, and of course more than enough living space as well. In fact, many luxury penthouses in Chicago have four to six bedrooms and the buildings also provide access to a wide-range of high-end lifestyle amenities that include a swimming pools, round the clock door and concierge service, state of the art fitness centers, heated garage parking, and so much more. 

Search Top-Floor Condos in Chicago's Hottest Neighborhoods

As you probably already know, most of Chicago's neighborhoods are filled with low-to-mid-rise condo buildings that have between 3 and 6 floors. And while top-floor condos inside these buildings can technically be classified as a penthouse, most people tend to associate the word "penthouse" with a high-rise unit well above the 3rd, 4th, 5th, or 6th floor. Regardless of classification or terminology, however, top floor condos for sale in Chicago are still highly sought-after, which is why we've made it easy to search these units by neighborhood below. 

A closer look at penthouse condos in Chicago

As the birthplace of the skyscraper, Chicago has adopted the penthouse concept quite nicely, and just like in New York, many of Chicago’s most sought after condos rest atop very high-end condo buildings like Trump Tower, the Ritz Carlton Residences, Waldorf Astoria Chicago, and The Palmolive—just to name a few. Today, most condo buildings in Chicago have at least one penthouse residence, and in many instances, buildings now include several penthouse “floors,” which anymore were implanted into newer construction condo buildings mainly for marketing purposes. The allure of living in a penthouse certainly has marketability, especially today, where the market is so competitive and developers are trying to give their buildings any advantage possible.  

Contact me for information regarding Chicago penthouses for sale  

For many luxury home buyers in Chicago, there’s nothing quite like living in a penthouse and they’ll stop at nothing to find the perfect penthouse unit. Luckily for them, and you, we’ve now made it much easier to find the Chicago penthouse residence of your dreams. And the most luxurious penthouses in Chicago offer buyers stunning views, the finest finishes, and first-class amenities on-site. So to see any of the penthouse properties listed above in person, please contact us at your earliest convenience.

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 Berkshire Hathaway HomeServices KoenigRubloff Realty Group are marked with the Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (a little black house) 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 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. Information deemed reliable but not guaranteed.

Listing information last updated on May 16th, 2021 at 6:30am CDT.