Most Expensive Homes for Sale in Chicago, IL Right Now
Last updated: April 24, 2025
Homes for sale in Chicago have a median list price of $370K, but luxury homes can be listed for much more. Here are the ten most expensive homes for sale in Chicago right now.
About this home
Once-in-a-life time opportunity to own one of Chicago's iconic estates, showcasing over 25,000 Sq. Ft. of combined living spaces and situated on nearly a third of an acre on Gold Coast's most coveted Astor street. This palatial architectural masterpiece designed by Howard Van Doren Shaw for the Goodman Family graces the market for the first time in 40 years, promising to leave you speechless. A true hallmark of Chicago's rich history, Astor Court has long captivated passersby with its magnificent neo-classical/Georgian Revival architecture spanning an impressive 80' feet across. This distinguished estate is centered around a one-of-a-kind tremendous courtyard, meticulously landscaped with lush gardens and flowing fountains, transporting you to the tranquil Italian countryside, creating a peaceful sanctuary in the vibrant urban setting. The main residence of the estate features over 10,000 sq. ft. of exquisitely renovated grand spaces blending timeless elegance with modern luxury. No expense was spared in creating this treasure, presenting a rare opportunity to own a coveted piece of Chicago's history. Every inch of the home exudes sophistication and grandeur offering unparalleled living experience featuring 13' ceilings, venetian plaster walls, incredible intricate millwork and hardwood oak flooring throughout, fireplaces with magnificent original marble mantles, and gold plated fixtures. As you enter the home, you are immediately captivated by the grand sense of space, elegant design and a sweeping curved staircase that ascends to the expansive main living areas. Every room exudes scale and sophistication offering both beauty and functionality. There are five en-suite bedrooms, each with its own style and personality. The luxurious primary suite features beautiful lake views and a grand primary spa bath adorned with exquisite Italian marble. In addition to the main residence, Astor Court showcases six gorgeous unique rental units, each with its own distinct charm and character, generating significant income. The entire estate encompasses 45 rooms, 16 bedrooms, 17 baths and 18 fireplaces offering endless opportunities to expand the main residence or transform it into a sprawling multi-generational family compound. Currently, there are two parking spaces located directly behind the property with the option to convert the coach house into a garage for additional parking. This extraordinary estate is perfectly situated just steps from Michigan Avenue, the lakefront, parks, premier shops, favorite restaurants, and world-class entertainment.
About this home
A rare piece of Chicago's history, the Thompson House at 915 N. Dearborn stands as one of the Gold Coast's original architectural treasures. Designed in 1888 by Cobb & Frost, the renowned architects behind the Newberry Library and University of Chicago, this grand residence was among the first to define the Gold Coast neighborhood after the Great Chicago Fire. For the next century, it was owned and used by the Scottish Rite. The property was meticulously restored by its current owner beginning in 2009, blending 19th-century grandeur with modern luxury. The Thompson House is now a nationally registered Historic Landmark. This masterpiece preserves its rich past while offering a remarkably livable floor plan where history, elegance, and everyday comfort coexist effortlessly. Constructed from solid red rock, this 5-bedroom, 4.2-bathroom home spans 13,400 square feet, with an additional 1-bedroom, 1-bathroom carriage house above the 3-car garage. This home showcases exceptional craftsmanship with one-of-a-kind finishes and details throughout. Some of the elements include a refurbished original mosaic floor, custom millwork, hand-carved marble fireplaces from Italy, and custom stained glass. Throughout the home, all wood features, including beams, doors, and trim, are custom made from solid Honduras Mahogany, with intricate touches such as paneling and carving. The staircase, also Honduras Mahogany, was hand crafted to mimic the home's original balusters. Modern features include an elevator servicing all levels, a Control4 system, integrated audio and speaker systems, smart HVAC controls, and full smart home capabilities, making this home as functional as it is beautiful. Enter the home to a large parlor paneled in mahogany. The details greet you right away - hand carved columns, custom stained glass windows and doors, marble floors imported from Turkey, and a hand carved marble fireplace. The adjacent great room is full of natural light from the large, curved windows and south and west exposures. The great room has earned its name sake with a Swarovski crystal chandelier, a hand-carved, book-matched onyx fireplace from Pakistan, and exquisite mahogany woodwork with in-wall cabinetry. Silk wall coverings and marble flooring add to the grandeur. On the opposite side of the foyer you will find the kitchen overlooking the walled courtyard with fountains and fireplace. The kitchen area features two dining areas, high-end appliances, a large island, custom cabinetry, and a laundry room tucked away. The second level landing showcases a stunning library framed by an intricate hand carved arch. You will also see the custom stained glass dome skylight up above. The second floor features the luxurious primary suite, complete with a wet bar, and en-suite bath, and a second bedroom or office with an en-suite bath. You will also find a screened in 3-season porch. On the top floor, there is a sitting room, three additional bedrooms, including two rooms sharing a Jack-and-Jill bathroom, and a third large bedroom with its own en-suite bath. The lower level is designed for relaxation and entertainment, featuring two seating areas, a bar, and a spa. The media area includes a hand-carved Italian Botticino marble fireplace and marble floors with bronze inlay. The galley bar offers an in-wall wine display, and the spa features a sauna, jacuzzi, steam suite, spa dressing rooms, a massage and zen room, and an additional laundry area. A Murano glass mural with an integrated waterfall and glass-blown ceilings add unique artistic elements rarely found in modern homes. Across the courtyard, you will find the cozy coach house, perfect for guests or additional living space. The home includes a heated 3-car garage. The Thompson House is more than just a home; it's a timeless work of art that embodies elegance, craftsmanship, and luxury living in the heart of Chicago.
About this home
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 in this timeless home with an excellent floor plan. 360 degree panoramic views and a grand foyer with private elevator entrance welcome you in this Penthouse. Entertain in your formal living and dining rooms with unobstructed East views of Lake Michigan. Custom millwork throughout the home. Chef's kitchen with large eat-in area as well as a family room with spectacular views of Lake Shore Drive. Abundant sunlight in the South-facing primary suite, large luxurious en-suite bath with his/her vanities, and a massive walk-in closet. Three private outdoor spaces - custom jacuzzi on one deck, semi-enclosed balcony, and a 400sf roof deck with custom kitchen on the top of Park Tower overlooking the entire City. Five bedrooms on the main floor and two additional upstairs. The home is flooded with natural light. Added security features include facial recognition technology, lockdown mode, private elevator foyer locked for privacy, and 24hr building security. Renowned Park Hyatt Hotel amenities at your disposal - 24 hour fitness center, indoor pool, spa, in-room dining, and the acclaimed NoMi restaurant. 4 parking spaces included.
About this home
An oasis above the clouds, this one-of-a-kind penthouse comprises the entire 64th floor at the prestigious Park Tower on North Michigan Avenue. Spanning 8,500 SQFT, this 15-room apartment was meticulously crafted by the renowned architectural firm Marvin Herman & Associates and Interior Designer, Mitchell Turnbough. With a 360-degree view of the city, this unique residence is designed to provide an unobstructed panorama of Chicago's skyline. Access this penthouse via one of three elevators and a private elevator foyer, secured with custom designed filigree metal doors and state-of-the-art controls. Herman and Turnbough created a bold sense of exhilaration and drama as you step into the home. The entrance introduces the apartment's 12' ceiling grandeur with an allee of elegant, fluted columns wrapped in cream shagreen. Each space within the home has been purposefully designed to create a sense of majesty without traditional barriers, offering a fluid, uninterrupted walk around the apartment. The living spaces are open and conducive to modern family living, featuring high-level, durable finishes, and bespoke anegre wood paneling. The custom plaster cornice and walls were crafted by hand. Inspired by a vivid Ferragamo scarf, Turnbough enveloped the 2,400 SQFT grand living room and dining room walls in salmon-pink velvet. The space is further enriched with polished black granite floors and lacquered baseboards. The choice of red hues throughout the room enhances the natural light, creating a dynamic interplay of colors that shift with the day's arc, adding a sense of luxury and softness. This ensures the space is equally suited for stately celebrations and intimate gatherings, maintaining a sense of warmth and inclusion regardless of the event size. The dream kitchen features sprawling granite counterspace, top-of-the-line appliances, and is clad in impressive quarter cut figured anegre custom cabinets and wall paneling. A butler's pantry, a unique ovular island, and abundant storage complete the space. The kitchen opens to a great room showcasing spectacular lake and city views with north, east, and west exposures. This gracious space accommodates a breakfast room, a large family room, and a playful 8-person "porch swing, " at the west corner of the family room, which floats gracefully from the 12 ft ceilings. The corner primary suite occupies the entire south wing and enjoys abundant sun from southeast exposures and views of the lake and the city down Michigan Avenue. Clad in quarter cut figured English sycamore paneling, no expense was spared in the custom closet & dressing room where you will find copious hanging space, a three-way mirror and a center island. The closet also doubles as a panic room. A luxurious ensuite bathroom, accoutered entirely in a soft golden-green onyx with book matched creamy marbling and gilded gold fittings, enjoys southwest corner views & features heated floors, a steam shower & tub with west-facing views. A sizeable home office paneled in quarter cut figured English sycamore flanks one side of the primary suite while a large exercise room flanks the other side and leads to the west wing of the residence, which is dedicated entirely to four ensuite guest rooms. The owner paid special attention to structural integrity and sound insulation, ensuring a reposeful living environment amidst the bustling city. From an aesthetic perspective, even the door hardware was exclusively designed by Marvin Herman for this penthouse, creating a high level of customization. The home is equipped with automated shades, smart Control 4 integrated surround sound & TV system. This residence offers a rare opportunity to own a significant piece of Chicago's architectural innovation, where every detail has been crafted to ensure unparalleled elegance & comfort. Enjoy Renowned Park Hyatt Hotel amenities at your disposal - 24 hour fitness center, indoor pool, spa, in-room dining, and the acclaimed NoMi restaurant
About this home
AAA+++ location on a 50x131 lot !!! The Savane Design + Build team presents the opportunity to create an exceptional custom new construction home on THE most desirable block in Chicago on a ultra rare double lot. This home offers 5 to 8 Bedrooms, 5 plus baths, state-of-the-art luxury finishes, expansive indoor/outdoor living spaces, lavish master suite, Front driveway access to your 4 plus car attached heated garage, and highlighted with a penthouse great room with walk-out terrace with unrivaled city views. Options include a 50 x 70 private "suburban sized" sanctuary like raised rear yard, sport court, in ground pool, and 5-stop elevator. Build from 6,000 sq ft to 14,000 sq ft. The integrated Savane Design + Build team, with their experienced in-house staff, provides a turnkey process to assist with putting your individual personal aesthetic on the home. Designs from Traditional to Contemporary. Photos are from a previous project and are for illustrative purposes.
About this home
Unique opportunity for the luxury homeowner who wants to provide an opportunity for an extended family habitat, live in nanny, or even business associates to be close in the huge coach house over the attached 5 car garage. The coach house also could be a huge basketball court with not much effort. This outstanding renovation was customized to perfection by Soucie Horner for this current owner who wanted grandparents to be close to kids for the ultimate family experience. The coach house is connected to the main home via a glass enclosed masterpiece of a vestibule. The seller wants to share they used the coach house for grandma, and she has watched her four grandkids grow from birth to heading off to college, while keeping grandmother vital to the daily activities, using the home as multi-generational space. This will become your homestead for all relatives for all holidays. The current owners have had "celebrations of life", baptisms, graduation, marriage proposals, birthdays, and all holidays, whether it's in the side yard or the wine cellar that holds 20-30. It's one of the best entertaining home in Lincoln Park. Yes, the house has beautiful design, but the absolute specialness of living in this home is who is in it with you, and with the coach house, the choice is yours. From the moment you enter the classic, original gate, the house has a feeling of being a home with an oversized front porch, beautiful original detailing, massive windows and beautiful front door which showcases the grand foyer and ultimate wide staircase the moment you enter. The coach house also has the most outstanding wine cellar perfect complete with a dining table! The house itself is incredibly special. High end finishes throughout on this extra wide lot which also includes an entire side lot with a sport court, a separate private office and amazing grass and terracing which gets all day sun. The modern kitchen and great room all overlook this gorgeous outdoor space and provide the most amazing entertaining space; the home has been the backdrop to multitudes of parties. The second and third floors have an amazing 6 bedrooms with a huge top floor playroom/hang out space with a huge skylight. The primary bedroom is ultra luxe and has a full slab Violeta marble bathroom straight out of a magazine. This house can be the ultimate city home for the person who wants it all!
About this home
Set on an expansive 44-ft-wide lot on the most coveted block of one of Chicago's most prestigious streets, 1853 N Burling is an exceptional custom-built estate. Situated in the heart of Lincoln Park, this architectural tour de force seamlessly combines masterful craftsmanship & refined modern living. Designed for extraordinary living, every element of this home has been carefully curated to reflect enduring quality & timeless elegance. The home's distinguished facade is defined by hand-selected, water-struck custom brick, triple-hung windows, & a grand arched entry crowned by a handcrafted S. A. Baxter decorative doorknob. Upon entering, an elegant foyer & gallery hall unfold, w/ generous wall space ideal for showcasing a fine art collection. Designed for effortless living, the home includes a full-service elevator that provides seamless access to all levels. A graciously sized formal living room impresses w/ soaring 11-ft ceilings & a gas fireplace. Floor-to-ceiling windows frame picturesque tree-lined views, bathing the space in natural light. An adjacent formal dining room provides the perfect setting for both intimate dinners & large-scale entertaining. A jewel box of design, a powder room stuns w/ Venetian plaster walls & a custom Macassar ebony vanity topped in glass. At the heart of the home is a Christopher Peacock-designed kitchen, a true statement in luxury and functionality. Outfitted w/ marble slab countertops, Wolf, Sub-Zero, Bosch, & Broan appliances, & an oversized breakfast bar, the space is complemented by a fully appointed butler's pantry, featuring a 2nd dishwasher, Wolf warming drawer, Miele coffee station, & steam oven. The adjoining family room centers around a gas fireplace & opens to a light-filled breakfast room framed by French doors. These doors lead to a Saint Andrew's stone terrace with a built-in grill, overlooking the professionally landscaped grounds by J. W. Landscapes, complete w/ custom sport court. A sculptural, curved staircase connects the upper levels, crowned by a domed skylight w/ custom lens & a Bocci chandelier, casting a soft glow. The artisan-forged metal balustrade introduces architectural rhythm to the space. The primary suite is a serene retreat wrapped in fine millwork & thoughtful detail. The paneled sitting room w/ custom cabinetry doubles as a sophisticated home office. In the bedroom, a gas fireplace & high ceilings create a sense of grandeur, while French doors open to a private terrace overlooking a manicured garden. Bathed in natural light, the spa-inspired bath features an oversized steam shower, soaking tub, mahogany vanity w/ Calcutta marble, Lefroy Brooks fixtures, heated marble floors, & pocket doors. A richly appointed mahogany dressing room w/ integrated cabinetry & a dedicated packing station completes the suite. A professionally outfitted exercise room completes this level with full-height mirrors & reinforced rubber flooring for sound & stability protection. The 3rd level hosts 3 ensuite bedrooms, each filled w/ natural light & custom built-ins. A charming library w/ built-in shelving, a rolling ladder, & a large walk-in closet-already plumbed for a future bath-provides flexibility for a creative space or an additional bedroom. The laundry room features Electrolux washer & dryer, ample cabinetry, & marble countertop workspace. Ascend to the rooftop to take in panoramic skyline views, where a firepit, lounge seating, & outdoor dining space create the ultimate setting for alfresco living. The lower level offers radiant heated floors, a spacious recreation room, a custom wet bar, climate-controlled wine cellar, guest suite, full bath, & a mudroom that connects directly to the attached, heated 2.5-car garage. Enhancing daily comfort, the home is equipped w/ snowmelt system for the driveway, steps, & sidewalks. Designed to enhance everyday living, this residence includes a full irrigation system, outdoor landscape lighting, a state-of-the-art security system, & built-in speakers.
About this home
Once in a lifetime opportunity to live in the iconic duplex penthouse in The Palmolive. This unit covers approximately 7880 interior sq feet over two floors and a combined 660 sq ft of three exterior terraces. The second floor has 14ft ceilings, dental molding, wood paneling in original office which is now the master bedroom, closet space galore, exquisite master bathroom, office, game room and much more. Encompassed on the first floor is an enormous chef's kitchen, living room, dining room and 1 bedroom with ensuite bathroom. Not to mention a beautiful temperature controlled wine room the present owner installed in their multi million dollar renovation since they purchased it. Forever views abound from every direction. Also this unit comes with its own private elevator and 2 parking spaces. Brand new infrastructure for the entire unit, new hardwood floors, new finishes and the list goes on and on. Qualified buyers only please.
About this home
The Savane Design + Build team presents an exceptional turnkey custom new construction home on THE most desirable block in Chicago on an ultra-rare double 50' x 125' lot. This home offers 5 to 8 Bedrooms, 5 plus baths, state-of-the-art luxury finishes, expansive indoor/outdoor living spaces, lavish master suite, 5 plus car attached heated garage, and highlighted with a penthouse great room with walk-out terrace with unrivaled city views. Options include raised rear yard, sport court, in ground pool, and 5-stop elevator. Build from 6,000 sq ft to 14,000 sq ft. The integrated Savane Design + Build team, with their experienced in-house staff, provides a turnkey process to assist with putting your individual personal aesthetic on the home. Designs from Traditional to Contemporary.
About this home
Unparalleled 360 degree views from a full floor penthouse at The St. Regis Chicago. 11'4" foot ceilings and motorized window treatments throughout. Chef's kitchen boasts Snaidero cabinets, Quartzite counters, and Gaggenau appliances. Primary suite with spa-caliber bath. Generously sized secondary bedrooms with en-suite baths. Stunning views from all rooms with floor to ceiling windows of Lake Michigan, Navy Pier, Monroe Harbor and the City. East and West facing terraces. Ample storage throughout. Luxury 5-star amenities include indoor & outdoor pools, hot tub, fire pit, fitness & training rooms, private dining room, demo kitchen, private wine storage & wine tasting room, enclosed dog exercise area.
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