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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

$2,000,000 - $3,000,000 $3,000,000 - $5,000,000 Over $10,000,000
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451 E Grand Avenue Ph64, Chicago, IL - $12,250,000

Residential, Attached Single
  • 5 Beds
  • 6 Baths
  • 7,940 SQFT
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Introducing Penthouse 64 At One Bennett Park, A Robert A.m. Stern Building. A One-of-a-kind Full-floor Residence Defined By Exceptional Scale, Light, And Sweeping Lake And Skyline Panoramas. Encompassing Approximately 7,940 Square Feet, With 5 Bed...

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800 N Michigan Avenue Ph67, Chicago, IL - $12,250,000

Residential, Attached Single
  • 6 Beds
  • Baths
  • 8,690 SQFT
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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-fo...

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453 W Briar Place Ph-west, Chicago, IL - $4,795,000

Residential, Attached Single
  • 5 Beds
  • Baths
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Welcome To 453 West Briar Place In Chicago's East Lakeview Neighborhood, Just Steps From The Lakefront. From The Award-winning Builder Of 647 West Melrose Street And Numerous Custom Single Family Homes, This Boutique, Six-unit Building Covers Near...

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111 W Maple Street 3402-3404, Chicago, IL - $3,300,000

Residential, Attached Single
  • 2 Beds
  • Baths
  • 2,500 SQFT
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Rare Opportunity To Own This Gold Coast Penthouse Sitting Atop A Uniquely Constructed James Lowenberg Building. This 2,500 Sq. Ft. Luxury Home Designed By Marvin Herman Architects & Interiors Affectionately Known As "joyau Du Ciel" Offers Numerous...

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14 N Peoria Street 6h-7h, Chicago, IL - $3,299,000

Residential, Attached Single
  • 4 Beds
  • 4 Baths
  • 5,100 SQFT
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This Chicago Loft, Admired For Its Architectural Character, Sophistication, And Timeless Allure, Has Secured Its Place Alongside Those In New York And Paris As A Breathtaking Place To Live. Unfolding Across Three Expansive Levels, This Extraordina...

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415 E North Water Street 3205, Chicago, IL - $3,000,000

Residential, Attached Single
  • 3 Beds
  • 4 Baths
  • 9,279 SQFT
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Bring Your Vision-priced To Sell! Step Into The Pinnacle Of Luxury Living At The Prestigious River View Condominiums In Streeterville. This Rare Two-level Penthouse Residence Spans An Impressive 9,300 Square Feet, Offering An Unparalleled Blend O...

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Photo of Listing #12313746 CONTINGENT

416 W Deming Place 4, Chicago, IL - $2,995,000

Residential, Attached Single
  • 3 Beds
  • Baths
  • 3,430 SQFT
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Step Into This One-of-a-kind East Lincoln Park Penthouse, Expertly Designed By Luxury Lifestyle Design Group Soucie Horner, Flooded With An Abundance Of Natural Light With Custom Features Throughout. The Open Floor Plan Is Not Only An Example Of ...

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180 E Pearson Street 7203, Chicago, IL - $2,897,747

Residential, Attached Single
  • 4 Beds
  • Baths
  • 3,320 SQFT
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Penthouse Level, 72nd Floor, 4-bedroom, Northeast Corner, 3320 Square Foot Floor Plan At The Luxurious Water Tower Residences Featuring Impressive, Sweeping Lake, Park And City Views Framing Navy Pier To The East Exposure And Up To Evanston Along...

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333 W Hubbard Street 1006, Chicago, IL - $2,350,000

Residential, Attached Single
  • 3 Beds
  • 4 Baths
  • 5,020 SQFT
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Welcome To The Pinnacle Of Penthouse Living In The Heart Of River North. Spanning More Than 10,000 Square Feet Of Extraordinary Indoor And Outdoor Living Space, Residence 1006 Is A Home Unlike Anything Else On The Market - A Private Urban Sanctuar...

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257 E Delaware Place 10ab, Chicago, IL - $2,200,000

Residential, Attached Single
  • 4 Beds
  • Baths
  • 4,000 SQFT
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Few Residences In The Gold Coast Offer What Discerning Luxury Buyers Value Most: An Entire Floor To Themselves, Direct Private Elevator Access, Exceptional Scale, Historic Character, And The Quiet Privacy Of Boutique Living. At 257 East Delaware P...

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1839 N Dayton Street Ph-01, Chicago, IL - $2,200,000

Residential, Attached Single
  • 3 Beds
  • 2 Baths
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1839 North Dayton Street: The Pinnacle Of Lincoln Park Luxury Introducing A Highly Anticipated, Exclusive Collection Of New-construction Luxury Residences Situated On A Prestigious Residential Block In The Heart Of Lincoln Park. This Boutique D...

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200 N Dearborn Street 4700, Chicago, IL - $2,000,000

Residential, Attached Single
  • 3 Beds
  • 3 Baths
  • 2,957 SQFT
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Experience True Penthouse Living From This One-of-a-kind Full-floor Residence At 200 N. Dearborn, Offering Nearly 3,000 Square Feet Of Sophisticated Interior Space Paired With An Extraordinary 2,350-square-foot Private Rooftop Terrace Connected By...

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1629 N Burling Street 3, Chicago, IL - $2,000,000

Residential, Attached Single
  • 4 Beds
  • Baths
  • 2,579 SQFT
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This Stunning 4-bedroom, 3.1-bathroom Duplex Penthouse In The Heart Of Lincoln Park Has A Thoughtfully Designed Floor Plan, Refined Finishes, And Exceptional Indoor/outdoor Living. The Main Level Is Designed For Daily Living And Effortless Enterta...

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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 August 15th, 2026 at 7:44am CDT.