Most Expensive Homes for Sale in Chicago, IL Right Now
Last updated: October 7, 2026
Homes for sale in Chicago have a median list price of $385K, 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
Presenting an unparalleled opportunity to acquire one of Chicago's most distinguished estates - an historic residence offering over 25,000 square feet of total living space, set on nearly one-third of an acre along the Gold Coast's prestigious Astor Street. This is an exceptionally wide and long lot like no other. Originally designed by acclaimed architect Howard Van Doren Shaw for the Goodman Family, this extraordinary property is being offered for the first time in 40 years. A true masterpiece, this estate stands as a defining example of neo-classical and Georgian Revival design and spans an impressive 80 feet across and embodying Chicago's rich architectural heritage. At the center of the estate lies an exceptional private courtyard meticulously landscaped with formal gardens and fountains. This serene outdoor space evokes the tranquility of the Italian countryside, creating a private sanctuary within one of the city's most vibrant neighborhoods. Originally a single-family home, now an owner's home plus high end leased residences, is easily reverted back to a single-family home with a garage. The main residence encompasses more than 10,000 square feet of elegantly renovated interiors, combining timeless sophistication with modern luxury. Every detail reflects impeccable craftsmanship - from the soaring 13-foot ceilings and Venetian plaster walls to the intricate millwork, oak hardwood floors, and original marble fireplaces. A grand curved staircase welcomes you upon entry, setting the tone for the refined living spaces beyond. The home offers five en-suite bedrooms, each with its own unique design and character. The primary suite provides sweeping lake views and a luxurious spa-inspired bath finished with exquisite Italian marble. Complementing the main residence are six distinctive units that are currently leased -each offering individual charm and contributing significant income potential. In total, the estate comprises 45 rooms, 16 bedrooms, 17 baths, and 18 fireplaces, offering endless possibilities - from an expanded private residence to a magnificent multi-generational estate. Additional features include two parking spaces located directly behind the property, with the option of converting the existing coach house into a garage for further parking accommodations. Ideally positioned just steps from Michigan Avenue, the lakefront, parks, fine dining, luxury boutiques, and cultural attractions, this remarkable estate represents a rare opportunity to own a truly iconic piece of Chicago's history and architectural legacy.
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 refurbished exterior sgraffito walls and granite mosaic, 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
This is an exceptional opportunity for a completely custom home in one of the most desirable Gold Coast buildings. Spanning nearly 12,000 square feet across two levels with three beautiful exposures, this estate-like property is the perfect city home. Enjoy boutique style living in a building with first class service. Designed by the late David Easton in collaboration with Eric J. Smith, this home was built to easily host large gatherings while still enjoying the comforts of day-to-day living. The gracious limestone foyer is a most beautiful receiving area, with gorgeous and intricately designed moldings and lighting all which leads to an amazingly sunny gallery and rotunda. The professional grade kitchen features the highest quality appliances, ample prep space, plus a separate butler pantry and catering space. Flanking either side of the kitchen are a breakfast room to the east for everyday dining, and an oversized dining room to the west for hosting more formal gatherings. The breakfast room features a custom, dual sided aquarium for living art and opens into the family room with rounded windows overlooking Lake Michigan. The formal living and library spaces are clad in Nordic pine and face east for spectacular lake views. Two exceptional bedroom suites, a well outfitted mudroom/family entrance, an art studio/project room, and an extra-large laundry room complete the east side of the home. A private fitness center, a media room, multiple wet bars/kitchenettes, and an extensive wine cellar all add to the main level of the home. Each room has details that one only finds in the most custom and detailed of properties. A classic staircase leads to the second level of the home, which is dedicated solely to bedroom suites, allowing for the utmost in privacy. The expansive primary suite offers a generously sized east-facing bedroom with privacy sound glass, dual baths and dressing rooms, as well as a separate study or sitting room. Three additional bedroom suites all offer wonderful closet space and nicely appointed incredibly detailed ensuite bathrooms. Enjoy six private terraces, state of the art audio visual, and sensational storage throughout in addition to seven premium garage parking spaces and three storage spaces. This is truly a one-of-a-kind home with too many details to list! 65 E Goethe features 24-hour door-staff and a beautifully designed rooftop terrace with spectacular city views.
About this home
Presenting an unparalleled opportunity to own a significant residence within one of Chicago's most distinguished historic estates, ideally situated along prestigious Astor Street in the heart of the Gold Coast. Originally designed by acclaimed architect Howard Van Doren Shaw for the Goodman family, this extraordinary property is a defining example of Neoclassical and Georgian Revival architecture and an enduring piece of Chicago's architectural legacy. Offered for the first time in 40 years, this remarkable condominium residence encompasses more than 14,000 square feet of total living space, including the main residence, a private one-bedroom service apartment, and a stand-alone one-bedroom coach house which easily accommodates 4 cars if turned back into a garage. This is an extraordinary combination of scale, flexibility, and privacy rarely found in condominium living. The historic estate spans an impressive 80 feet along Astor Street and is centered around an exquisite private yard, meticulously landscaped with formal gardens and fountains. Evocative of the Italian countryside, this enchanting outdoor sanctuary provides an exceptional sense of serenity and seclusion in the heart of the city. This main residence condominium alone encompasses more than 13,000 square feet of beautifully renovated interiors, where historic grandeur is seamlessly balanced with sophisticated modern luxury. Soaring 13-foot ceilings, Venetian plaster walls, intricate millwork, oak hardwood floors, and original marble fireplaces speak to the exceptional craftsmanship and architectural pedigree found throughout. A magnificent curved staircase creates a dramatic first impression and sets the tone for the gracious living and entertaining spaces beyond. The home offers five beautifully appointed en-suite bedrooms, each with its own distinctive character. The exceptional primary suite enjoys sweeping views toward Lake Michigan and features a luxurious spa-inspired bath finished in exquisite Italian marble. Adding to the rarity of the offering is a private one-bedroom service apartment, providing ideal accommodations for staff, guests, or extended stays. A separate approximately 1,300-square-foot, one-bedroom coach house offers yet another level of flexibility and privacy and may also present the opportunity to be reimagined as an exceptionally rare four-car garage. This is condominium ownership on an entirely different scale, the grandeur, privacy, and architectural significance of an Astor Street estate combined with the ease and convenience of condominium living. Perfectly positioned just moments from Michigan Avenue, the lakefront, neighborhood parks, celebrated restaurants, luxury boutiques, and Chicago's world-class cultural institutions, this extraordinary residence represents a rare opportunity to own a piece of Chicago history within one of the Gold Coast's most iconic architectural settings.
About this home
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-foot ceilings, 5-Star Hotel amenities, 700sf of private outdoor space atop the duplex, NoMi Club, and access to the best shopping and dining the Gold Coast has to offer. The crown jewel of Chicago is waiting for a buyer with discerning taste to create the most exceptional home in the City. Four dedicated parking spaces included.
About this home
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 bedrooms, 5 full bathrooms, and 2 powder rooms, this residence is thoughtfully composed and reflects the quiet confidence and refined detailing for which One Bennett Park is known. Designed with a seamless balance of sophistication and ease, the interiors by Soucie Horner Design Collective feature bespoke elements and an elegant material palette. The entry foyer with vaulted ceilings and direct elevator access makes a striking first impression. The custom-designed kitchen by 210 Design House effortlessly connects to the family room and is appointed with Italian cabinetry and a full suite of premium appliances, including Wolf, Sub-Zero, and Miele. A butler's pantry enhances functionality with a wine refrigerator, ice machine, and warming drawer. The combined living and dining areas are anchored by a ventless gas fireplace and framed by unmatched views. A separate family room with built-in millwork opens to a private north-facing terrace, while an additional terrace with southern exposure offers multiple outdoor living options. The expansive primary suite is a private retreat, complete with dual en-suite bathrooms, a walk-in dressing room, and multiple walk-in closets. A dedicated library with built-in alcoves provides the ideal setting for a home office or study. Interior finishes include rift and quartered white oak hardwood flooring throughout, prewiring for motorized shades with blackout capabilities in bedrooms, and thoughtfully designed lighting, including recessed art lighting and Lutron-controlled systems with customizable settings. Additional features include a utility room with full-size washer and dryer, laundry sink, and storage. Residents enjoy personalized 24-hour concierge services, and valet parking via a discreet porte-cochere, designed for both convenience and privacy. Our full suite of building amenities is unrivaled in Chicago and includes a world-class fitness center, yoga room, Pilates studio, salon and massage suite. The inviting 41st floor owner's lounge also offers residents a gracious gathering space with beautiful outdoor terraces, lounge area with fireplace, billiards room, private dining and cordial room. This highly anticipated penthouse is currently under construction and expected to deliver August 2026. Reach out to learn more about this unique offering. Two garage parking spaces with valet service included. An additional parking space available for purchase.
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
A full-floor penthouse of rare distinction, this residence at The St. Regis Chicago has been completely reimagined and elevated beyond its original delivery, emerging as a truly one-of-one offering within the Chicago market. Framed by sweeping 360-degree views, every room is immersed in a cinematic panorama of Lake Michigan, Navy Pier, Monroe Harbor, and the ever-evolving skyline-an uninterrupted dialogue between architecture and horizon. Arrive via a private elevator entry that opens directly into the residence, setting the tone for a level of privacy and exclusivity reserved for only the most exceptional homes. The interiors reflect a refined, globally inspired vision brought to life over the course of more than a year. This is not simply a developer-delivered residence, but a home that has been extensively transformed with custom architectural enhancements, bespoke finishes, and a meticulous attention to detail throughout. The residence is defined by a series of thoughtful architectural interventions that bring depth, structure, and cohesion to the interiors. The parlor has been fully built out with floor-to-ceiling steel-framed glass, creating a sense of intimacy while preserving openness and natural light. A dramatic full slab of imported Italian marble anchors the space, framed by integrated custom built-ins that add both scale and balance. In the dining area, a custom wine cellar has been thoughtfully incorporated, while floor-to-ceiling mirrored walls on the opposite side reflect Lake Michigan, allowing the presence of the water to be experienced from deeper within the residence. The family room is equally considered, anchored by a fully realized entertainment wall that brings both function and visual continuity to the space. Soaring 11-foot-4-inch ceilings and floor-to-ceiling glass enhance the extraordinary sense of volume and light throughout, while Lutron motorized window treatments provide effortless control and privacy. The chef's kitchen is both sculptural and highly functional, featuring Snaidero cabinetry, stone countertops and backsplash, a built-in coffee and espresso machine, and a full suite of Gaggenau appliances. The primary suite offers a serene, spa-like retreat, while each additional bedroom is generously scaled with its own en-suite bath, ensuring exceptional comfort and privacy throughout. Expansive east- and west-facing terraces extend the living experience outdoors, capturing sunrise over Lake Michigan and sunset across Chicago's iconic skyline-an extraordinary vantage point from which to experience the city throughout the day. Residents enjoy access to an exceptional collection of amenities, including the private residents' amenity floor on the 47th level-an elevated retreat featuring indoor and outdoor pools, a hot tub, state-of-the-art fitness and training facilities, private dining and demonstration kitchens, a wine storage and tasting room, golf simulator, and private cinema. Complementing the residential experience is The St. Regis Chicago hotel, home to Miru and Tre Dita, two of Chicago's most sought-after dining destinations, bringing world-class hospitality and culinary experiences just an elevator ride away. This is more than a residence-it is a true masterpiece in the sky, offering a level of design, craftsmanship, privacy, and lifestyle rarely seen in Chicago. A home that must be experienced to be fully understood, equally suited as a primary residence or an exceptional pied-a-terre within one of the world's great cities. The residence is offered unfurnished, with the opportunity to purchase the existing designer furnishings separately.
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
Introducing one of Chicago's most extraordinary trophy penthouse residences, a remarkable 92nd-floor home in the legendary John Hancock Center commanding uninterrupted 360-degree views of Lake Michigan, the skyline, and beyond. There is simply no other home in Chicago like this. Rising 1,010 feet above Michigan Avenue within one of the world's most architecturally significant buildings, originally designed by Skidmore, Owings & Merrill and forever woven into the identity of the city itself, this extraordinary penthouse delivers a living experience that very few homes in the world can replicate. Spanning approximately 7,700 square feet, this is not simply a high-rise condominium. It is a true landmark in the sky. Wrapped in dramatic walls of glass and framed by the Hancock's iconic architectural structure, the residence masterfully blends striking contemporary design with warm, refined interiors. Expansive living and entertaining spaces unfold with extraordinary scale and sophistication, creating an atmosphere that feels globally inspired, architecturally significant, and unmistakably luxurious. The formal living spaces transition effortlessly into a dramatic dining room anchored by a bespoke waterfall wall, an unforgettable statement piece designed to elevate entertaining at every level. Nearby, the expansive family room and sophisticated custom bar create a setting equally suited for intimate evenings or large-scale gatherings, while a discreetly positioned private office offers a quiet retreat above the city. Curated for elevated living, the residence also features a private theater with nine-person leather seating, a dedicated fitness studio, multiple lounge spaces, and thoughtful amenities seamlessly integrated throughout the home's remarkable floor plan. At the center of the home, the chef's kitchen is both sculptural and exceptionally functional, appointed with custom cabinetry, premium appliances including Sub-Zero, Wolf, and Miele, oversized stone surfaces, breakfast bar seating, and breathtaking panoramic views that transform everyday living into an extraordinary experience. Nearby, a beautifully integrated 61-bottle wine vault adds yet another layer of sophistication. The primary suite serves as a private sanctuary in the sky, a world unto itself. Designed with the comfort and refinement of a five-star hotel, the suite features its own sitting lounge and morning kitchen complete with Miele, Wolf, and Sub-Zero appliances, expansive custom-designed closets, and a luxurious spa-inspired bath overlooking the skyline. Heated floors, steam shower with body sprays and rainfall feature, towel warming drawer, designer vanity mirrors, and a dramatic waterfall-edge soaking tub framed by endless city views create an experience unlike anything else in the market. Additional bedroom suites offer exceptional comfort and privacy for family and guests alike, each thoughtfully appointed with elevated finishes and spa-quality baths. Rich natural stone, architectural lighting, custom millwork, elevated contemporary finishes, and world-class amenities define every inch of this extraordinary residence. Located steps from Chicago's Magnificent Mile, Oak Street Beach, premier dining, luxury shopping, and the lakefront, residents enjoy access to full-service amenities including 24-hour door staff, indoor pool, fitness center, dry cleaner services, receiving room, on-site management, and more. This is more than a penthouse. It is one of Chicago's true trophy residences, a once-in-a-generation opportunity to own an extraordinary architectural statement above one of the world's great cities.
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