Most Expensive House in Chicago: Top 5 Luxury Homes Ranked by Price

Chicago is home to some of the Most Expensive House in Chicago. The city’s current record-holder is a 25,000-square-foot mansion at 1932 N. Burling Street in Lincoln Park, which sold for $15.25 million in 2024. Beyond the city, a lakefront estate in Winnetka surpassed $31 million, highlighting the region’s thriving ultra-luxury market alongside historic mansions, modern estates, and exclusive penthouses.The biggest house here is 1932 N. Burling Street, spanning 25,000 square feet across eight city lots in Lincoln Park. Built in 2010 by Richard and Michaela Parrillo, it dwarfs every other property, including Windsor House, on this entire list.

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Most Expensive House in Chicago Priciest Mansion Quick Facts

The most expensive house in Chicago is the mansion at 1932 N. Burling Street in the Lincoln Park neighborhood. It sold for $15.25 million in August 2024, making it the highest-priced single-family home sale ever recorded within the city of Chicago itself.

Richard Parrillo, CEO of United Automobile Insurance Group, and his wife Michaela bought the land for $12.5 million in 2005, then spent $65 million building it. Architect Thomas Beeby, who designed the Harold Washington Library, created this custom statement piece.

Where Are These Most Expensive House in Chicago Located?

These six homes span Chicago’s top neighborhoods. Burling Street sits in Lincoln Park near Lake Michigan. Windsor House is in Winnetka. Ken Griffin’s floors and the Thompson House sit in the Gold Coast. Both penthouses are in Streeterville, near downtown.

My Personal Tour of Most Expensive House in Chicago

As Stefano Schiavon from RivonHome, touring these remarkable Most Expensive House in Chicago gave me a deep appreciation for their unique character. From grand staircases and historic gardens to elegant marble fireplaces and breathtaking penthouses, each residence reflected exceptional craftsmanship and thoughtful design.

What impressed me most was that every home had its own personality, proving that true luxury is created through timeless architecture, attention to detail, and genuine passion.

5 More of the Most Expensive Homes In and Around Chicago

The Burling Street Most Expensive House in Chicago holds the record for the city of Chicago. But if you widen the lens to the greater Chicago area — and include condos, not just houses — a few other properties are just as impressive.

1. The Windsor House, Winnetka — $31.25 Million

• Location: 419 Sheridan Road, Winnetka, behind a gated entrance on Lake Michigan
• Bedrooms: 7 bedrooms, plus a separate 2-bedroom coach house
• Bathrooms: 9 full bathrooms and 4 half bathrooms

This is technically the highest price ever paid for a home anywhere in the Most Expensive House in Chicago, though it sits in the North Shore suburb of Winnetka, not the city itself. Built in 1928 for Popular Mechanics publisher Henry H. Windsor Jr., the French Renaissance Revival estate sold in 2025 for $31.25 million.

It has 22 rooms, 223 feet of private Lake Michigan beachfront, a boathouse, and an infinity pool. The sellers, former Goldman Sachs partner Muneer Satter and his wife Kristen Hertel, had spent between $65 million and $72 million restoring it.

2. Ken Griffin’s Gold Coast Penthouses — $58.8 Million

• Location: 9 W. Walton Street, Gold Coast, Chicago
• Bedrooms: Not publicly disclosed — spans multiple combined floors
• Bathrooms: Not publicly disclosed — customized across combined units

Billionaire Ken Griffin holds the record for the single largest residential purchase in Chicago’s history, spending $58.8 million to combine multiple floors at 9 W. Walton St. in the Gold Coast back in 2017. It’s not one traditional house — it’s a stacked, custom-combined penthouse — but no other residential deal in the city has topped that dollar figure.

3. The Thompson House, Gold Coast — Currently Listed

• Location: 915 N. Dearborn Street, Gold Coast, across from Washington Square Park
• Bedrooms: 6 bedrooms
• Bathrooms: 6.5 bathrooms, plus a full lower-level spa suite

Built in 1888 by architects Cobb & Frost (the firm behind the Newberry Library), this 13,400-square-foot home on N. Dearborn is one of the original architectural landmarks of the Gold Coast.

It’s now a registered historic landmark, restored with hand-carved Italian marble fireplaces, Honduras mahogany woodwork, and a fully equipped lower-level spa. It’s a rare example of a 19th-century mansion brought fully up to modern living standards without losing its character.

4. Park Tower Penthouse, Streeterville — Full 64th Floor

• Location: 800 N. Michigan Avenue, Streeterville, Chicago
• Bedrooms: 5 bedrooms
• Bathrooms: 5 full bathrooms and 1 half bathroom

This 8,500-square-foot penthouse takes up the entire 64th floor of Park Tower on North Michigan Avenue. Designed by Marvin Herman & Associates, it has 360-degree skyline views, a private elevator foyer with custom filigree bronze doors, and access to Park Hyatt hotel amenities like an indoor pool and spa. It’s proof that Chicago’s most expensive homes aren’t limited to houses — some of the priciest addresses are in the sky.

5. Penthouse 66, One Bennett Park — Raw Full-Floor Residence

• Bathrooms: Not fixed — configured by the buyer during build-out
• Location: 451 E. Grand Avenue, Streeterville, Chicago
• Bedrooms: Not fixed — sold as raw space for the buyer to design

Sitting atop Robert A.M. Stern’s One Bennett Park tower, this 7,147-square-foot raw penthouse gives buyers a blank canvas with 13 to 20-foot ceilings and unobstructed lake and skyline views.

With only 69 total condos in the building, owners get access to a private lounge, fitness center, and dedicated valet — the kind of amenities you’d expect from a five-star hotel, not a condo building.

Comparing All 5 Most Expensive House in Chicago by Price

Windsor House is priciest here, yet smaller than Burling Street, which cost less. Ken Griffin’s combined floors cost more but aren’t one traditional footprint. Penthouses are smallest, yet priciest per square foot. Location and history drive price more than size.

Inside the Most Expensive House in Chicago Priciest Mansion: Interior And Other Features

As someone who has spent years studying materials, proportions, and craftsmanship, I can tell you — this house does not cut corners anywhere.

• A 25-foot by 25-foot foyer floored in marble imported from the French Pyrenees
• Custom-designed bronze entry doors weighing 1,000 pounds each
• A grand rotunda staircase finished in 22-karat gold repoussé
• A primary suite with a hand-carved marble fireplace
• A custom dressing room and private refreshment center
• Two guest bedrooms overlooking the private gardens
• A butler’s pantry connecting to the formal dining room
• A game room, media room, and library on the main level

Every room on the main and upper levels — the game room, media room, library, music room, formal dining room, and chef’s kitchen — was built to entertain on a grand scale. This isn’t a house you grow into. It’s a house designed from day one to impress.

Any Recent News on These Most Expensive House in Chicago?

Yes, there’s fresh news. Windsor House officially sold for $31.25 million in August 2025, setting a Chicago-area record. One Bennett Park’s Penthouse 64 recently relisted, fully finished, at $12.25 million.

The Thompson House remains actively listed in the Gold Coast. Burling Street and Ken Griffin’s floors haven’t resurfaced publicly since their sales. Chicago’s luxury market keeps shifting fast this year.

The Celebs and CEOs Own Most Expensive House in Chicago

A handful of well-known names have owned some of these trophy properties over the years:

• George Lucas & Mellody Hobson — The Star Wars creator and his wife bought a Park Tower penthouse for $18.75 million in 2015
• Ken Griffin — The billionaire hedge fund founder once owned the combined Gold Coast floors at 9 W. Walton before relocating to Miami
• JB Pritzker — Illinois’s governor paid $14.5 million for his Gold Coast mansion in 2006, the city’s price record before Burling Street
• Muneer Satter — The retired Goldman Sachs partner sold the Windsor House in Winnetka for a Chicago-area record $31.25 million

What Makes These Most Expensive House in Chicago So Expensive?

After studying buildings for most of my career, I can tell you the price of a home almost never comes down to just size. It’s a combination of a few specific things:

• Land scarcity — A parcel spanning eight city lots, like the one on Burling Street, almost never becomes available in a dense neighborhood like Lincoln Park.
• Custom architecture — Homes designed by a named architect, rather than built from a standard plan, cost significantly more and hold more long-term value.
• Rare materials — Imported marble, hand-carved stonework, and gold or platinum hardware are not mass-produced. Every piece is custom-made and installed by hand.
• Historic pedigree — Homes tied to a well-known architect or a notable original owner, like the Thompson House, carry value that has nothing to do with square footage.
• Views and location — Lakefront frontage, private beaches, and full-floor city views are physically limited resources. There’s only so much shoreline and so many top floors to go around.

Final Thoughts

What strikes me most about Most Expensive House in Chicago isn’t the price — it’s the craftsmanship behind them. A house like the one on Burling Street took years to plan and build, and every material inside it was chosen with intention. That’s the kind of thinking I try to bring into every project I write about, whether it’s a $15 million mansion or a small home renovation.

If you want to see how good design shows up in Most Expensive House in Chicago at every price point, take a look through our Home Decor section — there’s a lot to learn from how the best homes are put together, no matter their size.

FAQ About Most Expensive House in Chicago

Is the most expensive house in Chicago the same as the most expensive home in the Chicago area?

No. The most expensive house within Chicago’s city limits is the Burling Street mansion at $15.25 million. The most expensive home in the wider Chicago area, including suburbs, is the Windsor House in Winnetka at $31.25 million.

Where is the most expensive house in Chicago downtown?

The priciest downtown residences tend to be penthouses rather than houses, since downtown Chicago is dominated by high-rises. The full-floor penthouses at Park Tower and One Bennett Park are among the most expensive downtown residential properties.

What is the most expensive house in Chicago Gold Coast?

The Thompson House on N. Dearborn Street is one of the most valuable historic homes in the Gold Coast, along with Ken Griffin’s combined penthouse floors at 9 W. Walton St.

Are any of these Most Expensive House in Chicago still for sale?

The Thompson House, along with several penthouses at Park Tower, One Bennett Park, and the St. Regis Chicago, are currently listed. Prices and availability change often, so always check current listings before relying on a specific figure.