Looking for the most expensive houses in Chicago? From Lincoln Park to the Gold Coast, there are plenty of luxury homes, condos, and Chicago mansions that carry hefty price tags.

Not to mention, it’s 2024 and Chicago real estate prices are skyrocketing all around the city. But which Chicago homes for sale are the most expensive or priciest of them all?

most expensive houses chicago il

In this list of the highest-priced Chicago realty in recent memory, we’ll discover the most exciting and high-end properties ever sold in the city. We include giant city lots and massive penthouses with grand city views of Lake Michigan.

Likewise, we’ll compare Chicago living spaces and property prices to other major cities like Los Angeles and New York real estate. That in addition to learning the back story of Chicago’s richest residents like the Parrillo family and billionaire, Ken Griffin. Both of which own properties in Chicagoland that made our list this year.

Priciest Chicago Homes Criteria

Chicago’s incredible luxury real estate market provided more than enough to choose from when creating this list. From mansions to single-family homes, we’ll uncover the trend-setting living spaces that rank as the priciest in Chicagoland. In doing so, we’ll also uncover some of the most beautiful homes ever sold in the state of Illinois.

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Chicago Illinois Skyline

Instead of using sale price, square footage, or list price as the only criteria to rank Chicago’s most expensive homes, we decided to take another approach. Unlike Zillow, Curbed, or Redfin, we included multiple top categories.

Accordingly, this list includes the priciest homes sold, the most expensive Airbnb in Chicagoland, and the most expensive celebrity house sale.

Furthermore, we will venture outside of Chicago’s priciest areas like Lincoln Park and the Gold Coast. In particular, we cover neighborhoods like Englewood and an expensive Chicago suburban house in Glencoe.

Let’s start with the single most expensive house listing in Chicago history!

1. 1932 N Burling St In Lincoln Park

The most expensive Chicago home for sale ever is the Parrillo Mansion in Lincoln Park on Burling Street. Indeed, this “single-family” home spans 8 city lots and was custom built in 2010 by Richard and Michaela Parrillo for $65 million.

Most recently listed by Jameson Sotheby’s at $45 million, this sprawling estate is double the price of the next highest listing in the city of Chicago, IL.

Lincoln Park Mansion Burling

Even with record-low inventory levels, this luxury Lincoln Park Mansion has yet to attract even the most desperate buyer.

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2. 9 W Walton St In Gold Coast

The most expensive residence actually sold in Chicago is 9 W Walton St in the Gold Coast. This luxury property is a penthouse spanning the top four floors of a condo building downtown.

Originally four units, the four levels include 25,000 square feet of what was only raw space at the time of purchase. However, the purchase price reached $80 million when including remodeling costs.

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Luxury Penthouse Walton Gold Coast

A property this expensive could only be bought by a very wealthy individual. It’s no surprise that the owner of this uber-pricy pad is none other than billionaire Ken Griffin.

Indeed, he’s a serial luxury property collector notorious for some of the most expensive homes purchases in the United States. This includes 8 Star Island Drive, the most expensive house sold in Miami, Florida ever.

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3. 401 N Wabash Ave Unit 89A In River North

You might be surprised to learn that neither 9 W. Walton St. nor 1932 N. Burling St. holds the title for the highest price per square foot.

That belongs to this listing at 401 N Wabash Ave in the Trump Tower. Accordingly, Coldwell Banker Realty lists this condo at an extraordinary $2,103 per square foot.

Expensive Penthouse Wabash River North

Offering 360-degree views of Lake Michigan and a private elevator, this condo is 14,260 sq ft of endless potential. If that’s not impressive enough, some of the amenities include a 14,000 sq ft fitness center and four penthouse-level parking spaces.

4. 68 Locust Rd In Winnetka

Next on our list is Chicago’s largest mansion known as the Le Grand Reve Mansion. True to this list, 68 Locust Rd in Winnetka was once listed for a whopping $32 million dollars.

Correspondingly, this six-bedroom/ten-bathroom home spans 27,000 square feet. Likewise, it comes with a 9 car garage, fitness center, wine cellar, spa, and theater.

  • Address: 68 Locust Rd, Winnetka, IL 60093
  • House Price: Originally listed at $32 million, sold for 8.75 million in June 2020
  • Size: 27,000 sq ft, six-bedrooms, ten-bathrooms
Le Grand Reve Mansion Winnetka

Another key fact is that it’s the only home designed by famed-designer Richard Landry located east of Beverly Hills, California. After 11 years on the market, realtor Jena Radnay and her brokerage @properties sold this unbelievable property for $8.75 million in June of 2020.

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5. 5760 S Lafayette Ave In Chicago

Up next is one of Chicago’s oldest mansions, the John Raber House.

This historic home was constructed by John Raber in 1870 who was a prominent area businessman, real-estate developer, and politician. Furthermore, this two-story plus house is the only house on our list located in Englewood, a south side neighborhood in Chicago.

Historic Raber House Englewood

It’s famous for its once elaborate grounds and gardens as well as its rare pre-Chicago fire Italianate design. Additionally, the city-lot size is approximately 75’x100′ with the building size only reaching about 4,000 sq ft.

Though designated a Chicago city landmark in 1996, this once expensive home is in need of rehab. Unfortunately, this property may hold the title of the most forgotten Chicago mansion.

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6. 509 N Oak Park Ave (Oak Park, IL)

Number six on this list is the Hales Mansion located at 509 N Oak Park Ave. Actually, this opulent limestone castle is one of the most expensive Chicago homes to rent on Airbnb.

Its 9,500 square feet of living space includes six bedrooms and seven bathrooms, including the coach house.

Oak Park Hales Mansion Expensive Castle

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7. 50 Glade Rd In Glencoe

Built in 1903, the historic property was once a former chapel for the Jesuits and was later converted back to a single-family home. Amongst other accolades, this home was selected as the 29th Annual American Society of Interior Designers Showcase House.

Today, access to the entire castle is listed on Airbnb for around $5,500 a night.

It’s no surprise that Lake Shore Drive, and Burling Street are home to some of Chicago’s priciest residences. However, there are plenty of super expensive properties located in the suburbs as well.

In like manner, one of the most expensive suburban properties can actually be found at 50 Glade Rd in Glencoe.

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Northshore Glencoe Mansion

Located in Chicago’s ritzy North Shore the house overlooks the lake and has 8 bedrooms and 6.5 bathrooms. In addition, it was built in 1917 and boasts 15,800 square feet of living space.

Previous owners, David Helfand and Leslie Bluhm sold their beautiful property to Eric Lefkofsky in 2014 for a staggering $19.5 million.

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8. 159 E Walton St In Streeterville

Our next luxury home is considered the most expensive celebrity sale in the city. Located in Streeterville, 159 E Walton St was once owned by actor and Chicago native, Vince Vaughn. You can find this 12,000 square foot private penthouse atop the Palmolive building.

Vince Vaughn Walton Penthouse

Originally bought in 2006, the actor actually combined two separate penthouses to make a 12,000 sqft triplex.

In order to sell, he had to split up the property into two different listings again. As a result, one sold for $4.1 million and the other for $8 million. This made the collective total sales price $12.1 million, slightly more than it was bought for originally.

9. 1930 N Orchard St In Old Town

Let’s take a look at one Chicago home that recently set the record for the highest price tag of any residential sale in Lincoln Park. This newly built single-family mansion located at 1930 N Orchard St is a three-story row house with 10 bedrooms and six bathrooms.

Lincoln Park Record Expensive Home

It features large living spaces, with a notable dining room and living room that incorporate marble and hardwood floors.

What’s more, this expensive home sold in March of 2021 for $12.5 million in an off-market deal without being listed by any Chicago realtor or brokerage.

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10. 45 Lakeview Lane in Barrington, Illinois

We’ve seen some expensive homes with magnificent views of Lake Michigan, private elevators, and reflecting pools. Still, one luxury home in Barrington eclipses them all.

Indeed, this northwest suburban residential home was ranked by the Architectural Digest in 2017 as the most beautiful home in Illinois. According to Conlon/Christie’s International Real Estate, the booming 17,000 sqft home sits on 8 acres of land with a private terrace.

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Most Beautiful Home Barrington Hills

With an original list price of $9.95 million, it’s equipped with a built-in theater, floor-to-ceiling windows, a gorgeous family room, and plenty of old-world charm.

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High-Priced Property FAQs

Who is the richest person in Chicago?

Ken Griffin, the founder, and CEO of Citadel is the wealthiest resident of Illinois with a net worth of $27.5B. He is also the 54th richest person in the world.

What is the most expensive house in the United States?

A 105,000 square foot mansion in Bel Air, Los Angeles. The luxury house, known as “The One”, was listed for $295 million in January of 2022. This makes it the most expensive listing in the US.

More specifically, this megamansion has 21 bedrooms, 42 bathrooms, a 30-car garage, a 10,000-bottle wine cellar, and a 10,000 square foot sky deck.

A photograph of the author Andre Kazimierski
Written by
Andre Kazimierski
Founder, Improovy
Years Painting Experience
Houses Painted
More about the author
I have been building and scaling successful home service businesses for the past 17 years. Growing up in Chicago, I saw the struggles of contractors and small business owners first-hand. Having spent most of my life in home improvement, I founded Improovy to help bring trust back to the trades.

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