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
308 Properties Found. Page 1 of 13

This One-of-a-kind 2 Floor Penthouse Is An Ente...

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$8,990,000 Active

  • 3 Beds
  • 4 Baths
  • 9,300 ft²

Residential

415 East North Water Street #ph05, Chicago, IL

MLS® #10601929

This One-of-a-kind 2 Floor Penthouse Is An Entertainer's Dream-the Entire Top Floor Is Dedicated To It, With A Full Size Basketball And Racquetball Court, A Large Jacuzzi And Steam Room, And A Wraparound Porch With Endless, Unparalleled Views Of The Lake And City! Located In One Of The Most Covet...

Designed By Benjamin Marshall, This Extraordina...

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$8,885,000 Active

  • 3 Beds
  • Baths
  • 9,672 ft²

Residential

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

MLS® #10650886

Designed By Benjamin Marshall, This Extraordinary 9,600+ Sf Residence Is Being Offered For The First Time In 25 Years. Imagine Gatsby Style Entertaining In Grand Rooms Enriched With High, Detailed Ceilings And Fireplaces Throughout. Spanning Two Levels Of Elegance, Each Of The 23 Rooms Commands I...

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 ...

One Of The Most Sophisticated Homes To Come To ...

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$6,999,000 Active

  • 5 Beds
  • Baths
  • 5,913 ft²

Residential

1300 North State Parkway #1202, Chicago, IL

MLS® #10641245

One Of The Most Sophisticated Homes To Come To Market, Ph 1202 At The Ambassador Is In A League Of Its Own. Warm Modern Details Grace This 5913 Sqft Ph In The Heart Of Chicagos Most Sought After Neighborhood. Purchased As Raw Space And Reimagined By The Team At Wheeler Kearns, This Incredibly Bri...

This Dramatic Penthouse In A Classic Vintage Bu...

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$6,995,000 Active

  • 5 Beds
  • Baths
  • 7,462 ft²

Residential

189 East Lake Shore Drive #ph18, Chicago, IL

MLS® #10661498

This Dramatic Penthouse In A Classic Vintage Building On East Lake Shore Drive Has Been Completely Renovated With The Finest Of Materials. Over 7400 Square Feet Of Luxurious Finishes With Expansive Lake & City Views Plus An Additional 550 Square Feet Of Outdoor Space. The Over-sized Windows And E...

This Listing Has Floor Plan Pdf, Interactive Fl...

REDUCED 7% Photo of Listing #10300971
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$5,600,000 Active

  • 3 Beds
  • 5 Baths
  • 7,000 ft²

Residential

132 East Delaware Place #6302, Chicago, IL

MLS® #10300971

This Listing Has Floor Plan Pdf, Interactive Floor Plans And Walk Thru Movie As A Tour To Help With Remote Showings. All Floor Plans Are Also Pictures At The End Of The Unit Pictures. Bathed In The Ever-changing Dramatic Light Of The Lake And City, This Duplex Residence Commands Our World-class ...

An Unparalleled Penthouse With 1,000 Square Foo...

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$4,900,000 Active

  • 3 Beds
  • 4 Baths
  • 4,232 ft²

Residential

199 East Lake Shore Drive #ph10w, Chicago, IL

MLS® #10665036

An Unparalleled Penthouse With 1,000 Square Foot Private Terrace. Breathtaking, Unforgettable, Unobstructed Views Of Lake And City From Terrace And Residence. Penthouse Room Leads To The Terrace, Easily Accommodating 100 People For The Best Party In The City. 6 Hugely Oversized Windows Provide U...

Extraordinary Opportunity To Create A Gorgeous ...

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$4,500,000 Active

  • 3 Beds
  • 4 Baths
  • 4,836 ft²

Residential

199 East Lake Shore Drive #10e, Chicago, IL

MLS® #10650951

Extraordinary Opportunity To Create A Gorgeous Custom Home On Chicago's Most Iconic Street. The 10th Floor Is One Level Of A 10,000 Square Foot Residence (see Listing For 10-11e) That Is Being Offered Combined Or Divisible Into Two Spacious Homes. As It Is Currently Configured, You'll Find Grand...

Extraordinary Opportunity To Create A Gorgeous ...

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$4,500,000 Active

  • 4 Beds
  • Baths
  • 4,836 ft²

Residential

199 East Lake Shore Drive #11e, Chicago, IL

MLS® #10650938

Extraordinary Opportunity To Create A Gorgeous Custom Home On Chicago's Most Iconic Street. The 11th Floor Is The Top Floor Ph Of A 10,000 Square Foot Residence (see Listing For 10-11e) That Is Being Offered Combined Or Divisible Into Two Spacious Homes. As This Floor Is Currently Configured, You...

Experience "the Penthouse". This Massive, One-o...

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$3,890,000 Active

  • 4 Beds
  • Baths
  • 6,800 ft²

Residential

400 West Ontario Street #1801, Chicago, IL

MLS® #10651693

Experience "the Penthouse". This Massive, One-of-a-kind Property In The Heart Of River North. As You Enter The Sprawling 6,800 Square Foot Property Via Private Elevator, You Will Be Captivated By Soaring Floor-to-ceiling Windows Offering Unsurpassed Views Of The City Skyline. Spill Out Onto The A...

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

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$3,250,000 Active

  • 3 Beds
  • 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...

Rare Opportunity To Acquire Full-floor Penthous...

REDUCED 15% Photo of Listing #10555404
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$2,950,000 Active

  • 4 Beds
  • Baths
  • 6,000 ft²

Residential

888 South Michigan Avenue #ph2, Chicago, IL

MLS® #10555404

Rare Opportunity To Acquire Full-floor Penthouse In Prestigious Boutique Building With Unobstructed And Panoramic Views Of Chicago's Lakefront And Skyline. Designed By Holabird & Roche, This Classical Revival Is On The National Register Of Historic Places And Is A Must See! With A Keyed Elevator ...

Rare Vintage Full Rehab Off Lake Shore Drive! T...

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$2,695,000 Active

  • 4 Beds
  • Baths
  • 4,000 ft²

Residential

257 East Delaware Place #10ab, Chicago, IL

MLS® #10616450

Rare Vintage Full Rehab Off Lake Shore Drive! Tastefully Designed Full Floor Penthouse In Boutique, Historic Gold Coast Building. Elevator Opens Direct To Unit, This Sprawling 2019 Renovation Combined Two Units To Create An Expansive Floor Plan With Architectural Detail And Unsurpassed Quality. L...

3 Bedroom Residential Property in Chicago, IL

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$2,690,000 Active

  • 3 Beds
  • Baths
  • 4,297 ft²

Residential

130 North Garland Court #55b, Chicago, IL

MLS® #10603633

Bring Your Clients To This Most Unique Penthous...

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$2,500,000 Active

  • 5 Beds
  • 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...

Welcome To Mille - West Loop's Luxury New Const...

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$2,495,000 Active

  • 3 Beds
  • Baths
  • 3,800 ft²

Residential

1000 West Monroe Street #702, Chicago, IL

MLS® #10654238

Welcome To Mille - West Loop's Luxury New Construction Boutique Elevator Building! Only 2 Penthouse Opportunities Remain In This 12 Unit Building. Enjoy A Private Lifestyle In Your Ph Where There Are Only 2 Units Per Floor. This Duplex Ph Offers Almost 3800 S.f. Of Interior Living Space In Additi...

Welcome To Mille - West Loop's Luxury New Const...

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$2,395,000 Active

  • 3 Beds
  • Baths
  • 3,400 ft²

Residential

1000 West Monroe Street #701, Chicago, IL

MLS® #10654270

Welcome To Mille - West Loop's Luxury New Construction Boutique Elevator Building! Only 2 Penthouse Opportunities Remain In This 12 Unit Building. Enjoy A Private Lifestyle In Your Ph Where There Are Only 2 Units Per Floor. This Two-story Ph Offers Wonderful Interior Living Space In Addition To I...

This 47th Full-floor Penthouse Has An Astoundin...

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$2,350,000 Active

  • 3 Beds
  • 3 Baths
  • 2,957 ft²

Residential

200 North Dearborn Street #4700, Chicago, IL

MLS® #10579170

This 47th Full-floor Penthouse Has An Astounding Private Roof-top Terrace With Postcard Views In Every Direction. The Impeccable Construction Quality And High-end Design Is Immediately Evident As You Step Off The Elevator Directly Into The Gracious Foyer. This Leads To An Open Floor Plan With 1...

** Virtual Tour Available Anytime** Spectacular...

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$2,250,000 Active

  • 4 Beds
  • Baths
  • 6,088 ft²

Residential

910 South Michigan Avenue #1903, Chicago, IL

MLS® #10551511

** Virtual Tour Available Anytime** Spectacular 3000+ Sqft Private Terrace With Unobstructed Lake & Skyline Views! Over 6000+ Sqft Of Living Space Overlooking Millennium Park, Bean, Buckingham Fountain, Museum Campus, Pier! Impressive Foyer Greets You And Your Guests Upon Entry. Luxury Finishes T...

Upon Entering The Impressive Foyer, You'll Inst...

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$2,174,497 Active

  • 3 Beds
  • Baths

Residential

450 East Waterside Drive #3001, Chicago, IL

MLS® #10597308

Upon Entering The Impressive Foyer, You'll Instantly Notice The Exceptional Designer Influences Throughout. Over $625,000 In Upgraded Finishes Were Added To This Spectacular Penthouse W/11 Ft Ceilings! The Gorgeous Views Of The Lake, Navy Pier And Chicago River From Every Room Add To A Sense Of T...

Set Up A Showing Via Video Chat Or Preview This...

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$1,999,900 Active

  • 3 Beds
  • Baths
  • 4,357 ft²

Residential

600 North Kingsbury Street #506, Chicago, IL

MLS® #10630949

Set Up A Showing Via Video Chat Or Preview This Home Virtually: Listing Includes ***virtual Tour With Interactive Floorplans*** And ***full Resolution 4k Cinematic Walk Through ****rare Offering In The Heart Of River North - A Luxurious Three-story Penthouse With Panoramic Views Of The City, Rive...

West Loop Duplex Penthouse That Lives Like A Si...

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$1,999,900 Active

  • 4 Beds
  • Baths
  • 3,427 ft²

Residential

220 South Green Street #4n, Chicago, IL

MLS® #10602553

West Loop Duplex Penthouse That Lives Like A Single Family Home. This Intimate Eight Unit Elevator Building Allows You To Step Out Your Door And Into One Of The Best Areas Of Chicago. Close To Restaurants, Public Transportation, Shops, Whole Foods And More! This Amazing Space Boosts A Top Floor...

West Loop Duplex Penthouse That Lives Like A Si...

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$1,999,000 Active

  • 4 Beds
  • Baths
  • 3,427 ft²

Residential

216 South Green Street #4s, Chicago, IL

MLS® #10648264

West Loop Duplex Penthouse That Lives Like A Single Family Home. This Intimate Eight Unit Elevator Building Allows You To Step Out Your Door And Into One Of The Best Areas Of Chicago. Close To Restaurants, Public Transportation, Shops, Whole Foods And More! This Amazing Home Boasts A Top Floor ...

Distinct One Of A Kind 4800+ Sf Penthouse W/pri...

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$1,999,000 Active

  • 5 Beds
  • 3 Baths
  • 4,800 ft²

Residential

1157 West Erie Street #6, Chicago, IL

MLS® #10616582

Distinct One Of A Kind 4800+ Sf Penthouse W/private Elevator Entrance. This New Construction Home Features Superior Quality Incl Striking Two Tone All Brick Exterior, Flexicore Concrete & Attached 2 Car Parking. Located On A Prominent Corner, This Home Is Flooded W/light, Unmatched City Views & I...

 

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 March 29th, 2020 at 12:20pm CDT.