Chicago Homes with Penthouse Style

Welcome to the vibrant city of Chicago, Illinois, where the skyline is as iconic as the deep-dish pizza is delicious! Nestled in Cook County, Chicago is a bustling metropolis known for its rich history, diverse culture, and stunning architecture. From the majestic Art Institute to the picturesque Millennium Park, there’s always something to discover in this Windy City.

For those seeking a unique living experience, Chicago offers an exquisite selection of homes with penthouse-style living. Imagine waking up to breathtaking views of Lake Michigan, the Chicago River, and the famed skyline right from your own terrace. These luxurious penthouses are designed to provide an unparalleled lifestyle, featuring open floor plans, high ceilings, and modern amenities that cater to both comfort and elegance.

Whether you’re entertaining guests or enjoying a quiet evening, the spacious layouts and sophisticated finishes create an inviting atmosphere that feels like a personal retreat. Many penthouses also come equipped with private balconies, rooftop gardens, and access to exclusive building amenities such as fitness centers and lounges.

Living in a penthouse in Chicago means you’re not just investing in a home; you’re embracing a vibrant lifestyle. Enjoy the best of city living with easy access to world-class dining, shopping, and entertainment. From the bustling streets of the Loop to the artsy vibe of Wicker Park, every neighborhood has its own charm waiting to be explored.

Discover your dream penthouse in Chicago today and elevate your living experience to new heights!

Newest Chicago Homes with Penthouse Style

1001 W Madison Street Unit #710, Chicago image

1001 W Madison Street Unit #710, Chicago $975,000

Luxury corner penthouse in the heart of the West Loop, where breathtaking skyline views, designer finishes, deeded heated parking spot, and an exceptional floor plan crea...

3 Beds
3 Baths
12716485 MLS
NEW Status

1350 W Diversey Parkway Unit #3, Chicago image

1350 W Diversey Parkway Unit #3, Chicago $975,000

An exceptional 2 bed, 2 bath duplex UP set in an intimate, all-brick 3-unit building - where Lakeview and Lincoln Park connect. The WOW of this unit is the spacious famil...

2 Beds
2 Baths
12719308 MLS
NEW Status

2405 W Iowa Street Unit #402, Chicago image

2405 W Iowa Street Unit #402, Chicago $849,900

Better than new and hard to recreate at this price! This stunning penthouse residence at The Iowan combines the quality of luxury 2022 new construction with tens of thous...

3 Beds
2 Baths
12711917 MLS
NEW Status

1226 W Winnemac Avenue Unit #3S, Chicago image

1226 W Winnemac Avenue Unit #3S, Chicago — Andersonville $725,000

Modern, light-filled 2-bedroom penthouse in a beautiful historic Chicago greystone, tucked onto a quiet residential street in one of the city's most vibrant neighborhoods...

2 Beds
2 Baths
12716650 MLS
NEW Status
Andersonville Bldg.

4200 N Keystone Avenue Unit #3B, Chicago image

4200 N Keystone Avenue Unit #3B, Chicago $225,000

Charming and spacious top floor condo in the heart of Chicago's desirable Old Irving Park neighborhood! Separate living room and dining room with hardwood floors througho...

1 Beds
1 Baths
12717657 MLS
NEW Status

1523 N Western Avenue Unit #3A, Chicago image

1523 N Western Avenue Unit #3A, Chicago $770,000

Easy city living. Modern boutique elevator building. Walkable location. Bright, California-inspired design. This newer construction 3-bedroom, 2-bath home offers effortle...

3 Beds
2 Baths
12716745 MLS
NEW Status

611 N Noble Street Unit #3, Chicago image

611 N Noble Street Unit #3, Chicago $999,000

Rare full-floor duplex penthouse in West Town, crowned by an expansive private rooftop deck with spectacular unobstructed Chicago skyline views! Designed for indoor/outdo...

3 Beds
2 Baths
12716754 MLS
NEW Status

1919 S Prairie Avenue Unit #3, Chicago image

1919 S Prairie Avenue Unit #3, Chicago — Prairie District Homes $1,499,000

A true Chicago trophy residence, this extraordinary duplex penthouse crowns the legendary Marshall Field Jr. Mansion, one of the city's most historically significant esta...

3 Beds
3 Baths
12703203 MLS
NEW Status
Prairie District Homes Bldg.

2681 N Orchard Street Unit #3S, Chicago image

2681 N Orchard Street Unit #3S, Chicago $549,995

Welcome home to this beautifully updated top-floor residence on one of Lincoln Park's most picturesque, tree-lined streets. Blending timeless vintage character with thoug...

3 Beds
1 Baths
12715211 MLS
NEW Status

2072 N Western Avenue Unit #303, Chicago image

2072 N Western Avenue Unit #303, Chicago $950,000

*Construction Now Complete* Experience the pinnacle of modern luxury at THE ASH BUCKTOWN, one of the neighborhood's most exciting new developments. ***Unit 303 comes with...

4 Beds
3 Baths
12716618 MLS
NEW Status

2072 N Western Avenue Unit #PH-403, Chicago image

2072 N Western Avenue Unit #PH-403, Chicago $1,300,000

Experience the pinnacle of modern luxury at THE ASH BUCKTOWN, one of the neighborhood's most exciting new developments. This meticulously designed 4-bedroom, 2.5-bath pen...

4 Beds
3 Baths
12716549 MLS
NEW Status

2072 N Western Avenue Unit #PH-401, Chicago image

2072 N Western Avenue Unit #PH-401, Chicago $1,300,000

*Construction Now Complete* Come experience the pinnacle of modern luxury at THE ASH BUCKTOWN, one of the neighborhood's most exciting new developments. ***2 Indoor Heate...

3 Beds
3 Baths
12716479 MLS
NEW Status