Chicago penthouses are the epitome of luxury living, boasting the highest ceilings, expansive floor plans, spacious bedroom suites, and premium amenities like private pools and large outdoor terraces. With breathtaking Chicago views, penthouses offer one-of-a-kind layouts and finishing, setting the benchmark for sophisticated living and surpassing all others for premium residencies.
At 52 Stories Tall, This Leed Certified Building Stands Out Against The Historic Chicago Skyline. Optima Signature Was Intentionally Designed To Enhance The Modern Lifestyle With Its Sophisticated Finishes, Features, And Amenities. Spread Across 4...
60 East Randolph Street 24a, Chicago, IL - $12,635
Top Six Floors Are Available As Ultra High End Rental Homes Called The Penthouse Collection, These Homes Offer The Very Best Of Downtown Living With Spacious 3-4 Bedrooms Elegantly Equipped With A Gourmet Appliance Package (cove, Sub-zero, Wolf), ...
635 North Dearborn Street 2803, Chicago, IL - $12,000
You Will Love Living In This Stunning Two Story Penthouse With Floor To Ceiling Windows And Panoramic Views At The Caravel In The Heart Of River North. Newly Refinished Floors , Brand New Kitchen, New Lighting Throughout. Master And Second Bedr...
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60 East Randolph Street 25c, Chicago, IL - $10,874
Top Six Floors Are Available As Ultra High End Rental Homes Called The Penthouse Collection, These Homes Offer The Very Best Of Downtown Living With Spacious 3-4 Bedrooms Elegantly Equipped With A Gourmet Appliance Package (cove, Sub-zero, Wolf), ...
60 East Randolph Street 20d, Chicago, IL - $10,850
Top Six Floors Are Available As Ultra High End Rental Homes Called The Penthouse Collection, These Homes Offer The Very Best Of Downtown Living With Spacious 3-4 Bedrooms Elegantly Equipped With A Gourmet Appliance Package (cove, Sub-zero, Wolf), ...
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 4th, 2025 at 11:08pm CST.