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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 $5,000,000 - $10,000,000
Over $10,000,000
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451 East Grand Avenue Ph64, Chicago, IL - $12,250,000

Residential, Attached Single
  • 5 Beds
  • 7 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 North Michigan Avenue Ph67, Chicago, IL - $12,250,000

Residential, Attached Single
  • 6 Beds
  • 7 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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189 East Lake Shore Drive Ph18, Chicago, IL - $5,950,000

Residential, Attached Single
  • 5 Beds
  • 6 Baths
  • 7,462 SQFT
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Amazing, Dramatic Penthouse In A Classic Vintage Building On East Lake Shore Drive! This Home Has Been Completely Renovated With Over 7400 Square Feet Of Luxurious Finishes And Offers Expansive Lake & City Views Plus 2 Terraces With 550 Square Fee...

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

Residential, Attached Single
  • 5 Beds
  • 6 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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Photo of Listing #12623674 CONTINGENT

900 West Washington Boulevard Phw, Chicago, IL - $3,750,000

Residential, Attached Single
  • 5 Beds
  • 6 Baths
  • 4,949 SQFT
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Discover The Best Of The West Loop In This Top-floor Duplex Penthouse At 900 West Washington, An Exclusive Leed Gold-certified Boutique Building Of Just 22 Homes. Sweeping Skyline Views Surround A Wraparound Terrace, While The Elevator Opens Direc...

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10 East Delaware Place 34a, Chicago, IL - $3,399,500

Residential, Attached Single
  • 3 Beds
  • 3 Baths
  • 3,100 SQFT
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Perched Atop The Prestigious "10 East" In Chicago's Sought-after Gold Coast, This Extraordinary Custom Penthouse Defines Refined Luxury. A Dramatic Foyer Wrapped In Rich Walnut Paneling Sets The Tone, Opening Into Expansive Living And Entertaining...

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Photo of Listing #12644150

422 West Deming Place 4, Chicago, IL - $3,300,000

Residential, Attached Single
  • 4 Beds
  • 4 Baths
  • 3,500 SQFT
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A Truly Rare Offering In East Lincoln Park, This Remarkable Penthouse Delivers Approximately 3,500 Square Feet Of Refined Interior Living Paired With An Equally Expansive 3,500-square-foot Private Rooftop Retreat. Thoughtfully Designed For Both Ev...

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180 East Pearson Street 7203, Chicago, IL - $3,100,000

Residential, Attached Single
  • 3 Beds
  • 4 Baths
  • 3,376 SQFT
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Enjoy Life At The Top! Exquisitely Appointed And Rarely Available Corner Penthouse At The Iconic Water Tower Residences With Take-your-breath-away Views Of Lake Michigan And The City Lights To The East, North And South, And Views Of The Lake From ...

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415 East 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 West Deming Place 4, Chicago, IL - $2,995,000

Residential, Attached Single
  • 3 Beds
  • 4 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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Photo of Listing #12646267

1942 North Sedgwick Street Ph, Chicago, IL - $2,850,000

Residential, Attached Single
  • 3 Beds
  • 3 Baths
  • 3,200 SQFT
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This Extraordinary Penthouse, Built As The Developer's Personal Residence, Is Being Offered For The First Time And Is A Rare Opportunity To Own This Masterpiece Crafted By The Highly Acclaimed Developer - Pld Homes. Nestled In The Highly Desirable...

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Photo of Listing #12527836 CONTINGENT

1955 North Halsted Street Ph, Chicago, IL - $2,750,000

Residential, Attached Single
  • 5 Beds
  • 4 Baths
  • 3,855 SQFT
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Set Atop A Boutique Three-unit Building In Lincoln Park, This Extra-wide Penthouse Duplex Offers The Scale And Presence Of A Single-family Home With The Ease Of Condominium Living. A Private Elevator Opens Directly Into The Residence, While An Att...

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333 West 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 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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1839 North Dayton Street Ph-02, Chicago, IL - $2,175,000

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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2042 North Burling Street Ph, Chicago, IL - $2,095,000

Residential, Attached Single
  • 3 Beds
  • 3 Baths
  • 2,900 SQFT
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Set Along A Quiet Cul-de-sac Directly Overlooking Oz Park, 2042 N Burling Street Ph Occupies A Position In Lincoln Park That Is Genuinely Difficult To Improve Upon. Surrounded By Green Space, Tucked Away On One Of The Neighborhood's Most Private A...

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323 South Racine Avenue Phd, Chicago, IL - $2,000,000

Residential, Attached Single
  • 5 Beds
  • 4 Baths
  • 3,103 SQFT
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Don't Miss This 2022 New Construction 5 Bedroom, 3.5 Bath Top Floor Corner Duplex Penthouse In Belgravia's Ca6, A Boutique Luxury Condominium Building Offering A Refined Interpretation Of West Loop Living. A Must See In Person To Appreciate The Qu...

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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 May 18th, 2026 at 7:24pm CDT.