Chicago Penthouses For Sale

Search Chicago Penthouse Condos

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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
419 Properties Found. Page 1 of 18

Finally!!! This Smart And Sophisticated 6,000 S...

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$8,500,000 Active

  • 3 Beds
  • 4 Baths
  • 6,000 ft²

Residential

21 East Huron Street 4501, Chicago, IL

MLS® #10840152

Finally!!! This Smart And Sophisticated 6,000 Sq/ft Penthouse, Sporting One Of Chicago's Largest High-rise "private" Residential Outdoor Living Space, Totaling 2,500 Sq/ft, Is Back On The Market!!! This Pinnacle Of Chicago Condominium Provides Spectacular 360-degree Views Of The Brilliant Chicago...

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® #10828487

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 ...

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

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$4,500,000 Active

  • 3 Beds
  • 5 Baths
  • 4,232 ft²

Residential

199 East Lake Shore Drive Ph10w, Chicago, IL

MLS® #10857212

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...

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

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$4,250,000 Active

  • 3 Beds
  • 4 Baths
  • 5,020 ft²

Residential

333 West Hubbard Street 1006, Chicago, IL

MLS® #10862021

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...

This Is An Absolutely Rare Opportunity To Own T...

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$4,150,000 Active

  • 8 Beds
  • 10 Baths
  • 7,800 ft²

Residential

550 North Saint Clair Street 2601-02-03, Chicago, IL

MLS® #10970651

This Is An Absolutely Rare Opportunity To Own The Entire Top Penthouse Floor And Create The Most Amazing Space In The City With Jaw-dropping 360-degree Skyline Views Through Floor-to-ceiling Windows, 13 Foot Ceilings And A 100 Foot Wide Outdoor Terrace!

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...

Sold Before Print The Orchard Private Residence...

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$3,500,000 Contingent

  • 4 Beds
  • 5 Baths
  • 3,596 ft²

Residential

2350 North Orchard Street 604, Chicago, IL

MLS® #11008785

Sold Before Print The Orchard Private Residences, A Plush And Comfortable New Construction Boutique Building Featuring 32 True Highly Designed Homes By Internationally Acclaimed Design Firm, Soucie Horner. Conceptualized With Thoughtful Attention To Quality Detail At Every Moment, Richly Appointe...

Fabulous Entire 48th Floor At The Fordham. Taxe...

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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

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 Lobby Bypassing The Door Staff If Desired. El...

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 Active

  • 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...

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...

If Only The Walls Could Talk! Playboy Founder, ...

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$2,895,000 Active

  • 4 Beds
  • 6 Baths
  • 4,100 ft²

Residential

1340 North State Parkway 4s, Chicago, IL

MLS® #10980336

If Only The Walls Could Talk! Playboy Founder, Hugh Heffner, Purchased 1340 N. State In 1959 And For The Next 15 Years, The Playboy Mansion Was Known For Its Lavish Parties Attended By Notable Celebrities Like The Rollings Stones. Heffner Lived Downstairs In The 72-room Mansion And The Playmates ...

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...

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

REDUCED 13% Photo of Listing #10843192
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$2,500,000 Active

  • 4 Beds
  • 4 Baths
  • 3,659 ft²

Residential

33 West Ontario Street Ph-d, Chicago, IL

MLS® #10843192

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...

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...

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

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$2,475,000 Active

  • 3 Beds
  • 3 Baths
  • 3,500 ft²

Residential

33 East Bellevue Place Ph-w7, Chicago, IL

MLS® #10990111

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 ...

Welcome To Unrivaled Penthouse Living At 330 S ...

REDUCED 6% Photo of Listing #10880719
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$2,250,000 Active

  • 3 Beds
  • 5 Baths
  • 5,600 ft²

Residential

330 South Michigan Avenue 1905, Chicago, IL

MLS® #10880719

Welcome To Unrivaled Penthouse Living At 330 S Michigan Ave. This 3 Bed, 4 And A Half Bath Luxury Estate Covering Over 5,500 Square Feet Across Three Floors, With One Of The Largest Private Rooftop Spaces On The Magnificent Mile, Is A Home Worthy Of An Ambassador. The Grand 2 Story Foyer With It...

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

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$2,250,000 Active

  • 4 Beds
  • 5 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...

Chicago's Premier Address Is In One Of The Most...

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$2,249,000 Active

  • 3 Beds
  • 4 Baths
  • 3,500 ft²

Residential

1000 West Monroe Street Ph701, Chicago, IL

MLS® #11002571

Chicago's Premier Address Is In One Of The Most Desirable Neighborhoods In The Country. You Will Covet This West Loop Penthouse From The Moment You Open Your Front Door. Offering An Exclusive Residence With Approx. 3500f Coupled With 20 Feet Of Window Walls, Sunshine Pours Into This Southeast Co...

 

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 3rd, 2021 at 5:16pm CST.