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Chicago Penthouses

Life at the Top in Luxury Condos 

Read more about Penthouses

Penthouse

Is it a buyer's or seller's market for penthouses and condos? Check by zip code

                                                                                           

Luxury Chicago Penthouses for Sale

$1,000,000 - $2,000,000 $2,000,000 - $3,000,000 $3,000,000 - $5,000,000
$5,000,000 - $10,000,000 Over $10,000,000
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800 North Michigan Avenue Ph67, Chicago, IL - $15,750,000

Residential, Attached Single
  • 6 Beds
  • 8 Baths
  • 9,250 SQFT
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Unparalleled Views From The Park Tower's Crown Jewel That Will Impress Even The Most Discerning Buyer. A Full Floor Duplex Penthouse Like No Other At Chicago's Premier Address, 800 N. Michigan, With 5-star Luxury Hotel Amenities. 12 Foot Ceilings ...

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451 East Grand Avenue Ph65, Chicago, IL - $15,170,000

Residential, Attached Single
  • 4 Beds
  • 6 Baths
  • 7,582 SQFT
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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 Lakef...

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1301 North Astor Street Ph, Chicago, IL - $5,500,000

Residential, Attached Single
  • 2 Beds
  • 3 Baths
  • 5,796 SQFT
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Opportunities Like This Rarely Come To Market. Expect To Be Enamored As You Step Into This Gold Coast Duplex Penthouse Topping A Historic Astor Street Art Deco Building. A Collaboration Between Designer Michael Smith And Architect Marvin Herman,...

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25 East Superior Street 4701, Chicago, IL - $5,500,000

Residential, Attached Single
  • 4 Beds
  • 6 Baths
  • 8,100 SQFT
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Tremendous Price Improvement For This Flawless, Design-forward, Full-floor Penthouse Residence At The Fordham, Complete With Five Private Terraces. Located On A Tree-lined Stretch Of Superior Street Just Steps Away From Chicago's Magnificent Mile,...

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445 East North Water Street E2705, Chicago, IL - $4,500,000

Residential, Attached Single
  • 3 Beds
  • 5 Baths
  • 7,000 SQFT
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Never Before Listed, Duplex Penthouse With Over Seven Thousand Square Feet Of Luxe Living Space, Conceived By Dwayne Macewen Of Dmac Architecture & Interiors, Under The Artful Eye And Keen Collaboration Of Its Original Owners. Unobstructed Views O...

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438 West Saint James Place Ph, Chicago, IL - $4,395,000

Residential, Attached Single
  • 5 Beds
  • 5 Baths
  • 4,215 SQFT
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Full Floor Penthouse Residence + Exclusive Use Of 2783 Sq Ft Rooftop Deck + Elevator Entrance To Home & Roof + Multiple Large Terraces + 4 En-suite Bedrooms + Family Room + Large 5th Bedroom Suite Or Grand Office Option With Terrace + Dressing Roo...

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132 East Delaware Place 6205-07, Chicago, IL - $3,950,000

Residential, Attached Single
  • 3 Beds
  • 4 Baths
  • 3,600 SQFT
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Luxury Reimagined At The Four Seasons Residences. Rest Assured, This Incomparable, Completely Renovated Penthouse Unit Is Just That, Incomparable And The Only One Of Its Kind. This Luxurious Penthouse Suite In Chicago's Gold Coast Offers An Unpara...

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21 East Huron Street 4801, Chicago, IL - $3,850,000

Residential, Attached Single
  • 4 Beds
  • 5 Baths
  • 5,143 SQFT
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Welcome To The Most Magnificent Full-floor Residence, With An Enormous East Facing Private Terrace And 5,140 Square Feet Of Luxurious Interior Living On One Floor, You Can Enjoy Incredible 360 Views Of The City. This One-of-a-kind Fully Renovated...

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1205 North Astor Street Ph, Chicago, IL - $3,800,000

Residential, Attached Single
  • 3 Beds
  • 4 Baths
  • 5,000 SQFT
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Beautifully Fully Furnished And Appointed Full Floor Penthouse In A Boutique, 6-unit Iconic Condominium Building On Premier Astor Street In The Heart Of The Gold Coast. Originally Designed By Chicago's Renowned Architect Benjamin Marshall, This St...

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438 West Saint James Place 3, Chicago, IL - $3,595,000

Residential, Attached Single
  • 4 Beds
  • 5 Baths
  • 3,810 SQFT
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Full Floor Residence + Private Elevator Entrance + Multiple Large Terraces + 4 En-suite Bedrooms + Family Room + Large 5th Bedroom Or Grand Office Option With Terrace + Dressing Room + Rare Opportunity In Boutique 4 Unit Building + Sharing Two Lo...

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1325 North Astor Street 13, Chicago, IL - $2,995,000

Residential, Attached Single
  • 6 Beds
  • 6 Baths
  • 7,900 SQFT
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Introducing A Towering Architectural Masterpeice In The Heart Of Chicago's Gold Coast, A David Adler-designed Duplex Home 2 Blocks From The Lake. As You Step Off The Elevator, You Are Immediately Transported Into What Feels Like A Parisian Apartme...

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676 North Kingsbury Street Ph01, Chicago, IL - $2,995,000

Residential, Attached Single
  • 4 Beds
  • 6 Baths
  • 5,349 SQFT
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Be The First To Enjoy This Brand New, Never-occupied 5,349 Sqft Penthouse At The Ronsley! Key Features Include Three Levels Of Dramatic Contemporary Living Space, Outdoor Space On Every Level, Panoramic City, Sunset, And River Views, And Two Prime...

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257 East Delaware Place 10ab, Chicago, IL - $2,500,000

Residential, Attached Single
  • 4 Beds
  • 5 Baths
  • 4,000 SQFT
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Gold Coast Charm Meets Modern Design At The Historic 257 E Delaware. Nestled Along The Prestigious Blocks Of Lake Shore Drive, This Boutique 12 Unit Building Welcomes You With Direct Elevator Access To A Thoughtfully Renovated Full Floor Penthouse...

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333 West Hubbard Street 1006, Chicago, IL - $2,450,000

Residential, Attached Single
  • 3 Beds
  • 4 Baths
  • 5,020 SQFT
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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...

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190 East Walton Place 703, Chicago, IL - $2,300,000

Residential, Attached Single
  • 4 Beds
  • 4 Baths
  • 4,200 SQFT
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Remarkable One Of A Kind Penthouse Apartment In Small 17 Unit Boutique Building-the Regent-in The Heart Of Streeterville/east Lake Shore Drive Area. Elegant 4,200 (approx.) Square Foot Floorplan With The Most Remarkable Private 3,000+ (approx.) Sq...

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33 West Ontario Street Ph-c, Chicago, IL - $2,200,000

Residential, Attached Single
  • 4 Beds
  • 4 Baths
  • 3,900 SQFT
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This Has The Wow Factor That Is Simply Unparalleled! Absolutely Stunning Duplex Penthouse In River North! Nearly 4,000 Square Feet Of Living In The Sky! You Will Immediately Be Spellbound By The Endless Views From The Wall Of Windows Surrounding T...

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Photo of Listing #11944879

1035 North Dearborn Street 18, Chicago, IL - $1,999,500

Residential, Attached Single
  • 4 Beds
  • 5 Baths
  • 3,600 SQFT
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Matterport/3d Virtual Tour Link Available! Gaze Out At The Lake & The Skyline & Walk To The Mag Mile & Everything The Gold Coast Has To Offer From This Nearly 3600sqft, Incredibly Bright & Model-caliber 86'+ Wide 4bd/3.2ba Full-floor Home (present...

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1035 North Dearborn Street 18, Chicago, IL - $1,999,500

Residential, Attached Single
  • 4 Beds
  • 5 Baths
  • 3,600 SQFT
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Matterport/3d Virtual Tour Link Available! Gaze Out At The Lake & The Skyline & Walk To The Mag Mile & Everything The Gold Coast Has To Offer From This Nearly 3600sqft, Incredibly Bright & Model-caliber 86'+ Wide 4bd/3.2ba Full-floor Home (present...

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The Appeal of Living in a Penthouse

Whether a penthouse is on the top floor of a six-story mid-rise or the 50th floor of a skyscraper, it is considered the most desirable condominium in the building. One reason is the view offered from an expansive outdoor space, set-back from the outer walls, to create large,private terraces, whereas other units on lower floors may just have a balcony.  

In keeping with the exclusivity, most Chicago luxury penthouses have keyed elevator landings with direct access to the apartment’s foyer, and often the ride is non-stop from the lobby to the residence. Although luxury penthouse apartments became popular in the 1920s, after the notoriety of the roof top residence at the Plaza Hotel overlooking Central Park, recent demand and buyers’ willingness to pay premium prices, encouraged developers to design buildings with multiple high-floor penthouses. Ironically, offering three or more penthouses in a building only increases the flurry of competition, and, often, they are the first luxury condos to sell in Chicago’s new developments, driving prices to soar along with the floor heights.

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The luxury real estate listings on this page include Chicago luxury penthouses and condos for sale with a minimum price of $1 million. The property listings are updated daily with new luxury condos for sale as they hit the market. Please contact us if you have an interest in purchasing a luxury condo in Chicago and would like to schedule a showing

Chicago Penthouses for Sale
Luxury Living in Chicago’s Penthouses

Real estate

Chicago Penthouses

Whether a penthouse is on the top floor of a six-story mid-rise or the 50th floor of a skyscraper, it is considered the most desirable condominium in the building, offering the best views and luxury amenities. Designed from the beginning to be marketed as an exclusive residence, architects take advantage of the building’s expansive roof-top space, set-back from the outer walls, to create large, private outdoor terraces, where as other units on lower floors may just have a balcony. In keeping with the exclusivity, most penthouses have keyed elevator landings with direct access to the apartment’s foyer, and often the ride is non-stop from the lobby to the residence. Although luxury penthouse apartments became popular in the 1920s, after the notoriety of the roof top residence at the Plaza Hotel overlooking Central Park, recent demand and buyers’ willingness to pay premium prices, encouraged developers to design buildings with multiple high-floor penthouses. Ironically, offering three or more penthouses in a building only increases the flurry of competition, and, often, they are the first luxury condos to sell in Chicago’s new developments, driving prices to soar along with the floor heights

Midwest Real Estate Data LLC Logo 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 Sotheby's International Realty 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. Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

Listing information last updated on December 11th, 2023 at 12:53pm CST.