Most Expensive House In Chicago (2022 Update)

Chicago Richest Residents

Chicago is the third-largest city in the United States, with over 2.7 million people.

Every city has its own distinct attractions, and Chicago is no exception. If you have a lot of money to spend, a city like Chicago will provide you with many housing options.

In this article, we’ll discover the best and high-end properties ever sold in the city and will later share how you can afford these houses too.

But before we go deeper…


This Most Expensive House In Chicago review has been thoroughly researched with information and testimonials that are available online to anyone in the public. Any conclusions drawn by myself are opinions.

1432 N. State Parkway
N State Pkwy Chicago Residence
Price: $7,499,000

Another Gold Coast property on the list is just down the street. The 9,100-square-foot, double-lot property has some of the original 1883 elements. A marble bathroom, a full-floor master bedroom, a guest suite in the coach house, and a planted side yard are one of the features.

68 Locust Rd In Winnetka
Locust Rd Mansion In Winnetka
Price: 8.75 million

Le Grand Reve is Chicago’s largest residence. This six-bedroom, ten-bathroom home spans 27,000 square feet. It has a 9-car garage, fitness center, wine cellar, spa, and theater.

It is also the only residence created by the famous architect Richard Landry located east of Beverly Hills, California.

924 N Clark St.
Price: $10.9 million

1916 substation transformed into a 15,000 square foot mansion with 6 bedrooms and 9 bathrooms on 4 levels. The house has a chef’s kitchen, wine cellar, rooftop deck, greenhouse, rec room, luxury bathrooms with large tubs, steam showers, and a meditation room.

199 E. Lake Shore Drive, Unit 10-11E
Price: $11,500,000

This 9,600-square-foot Benjamin Marshall-designed home is for auction after 25 years. It has a grand rec room with pool table, huge kitchen with fireplace, magnificent dining room, skylights, and conservatory attached to a large terrace.

11 E Walton St, Unit 5200
Price: $11.7 million

A 4-and-a-half-bathroom condo occupies the Waldorf Astoria’s entire 52nd floor.

Floor to ceiling windows and various terraces provide unrivaled city views. Inside, there’s a glass-enclosed wine cellar, bar, home theater, and master suite with a bathroom and closet larger than most living rooms. This multi million dollar home has a private indoor pool. Residents also enjoy concierge services, 24-hour room service, and valet parking.

9 W. Walton St. in Gold Coast 2018
Gold Coast W Walton St
Price: $12.1 million

When Ilan Shalit, co-founder of Consolidated Trading LLC, bought a full-floor unit, he paid the second-most for a condo in that building behind Ken Griffin, Illinois’ richest person and founder of hedge fund Citadel. Ken Griffin bought the top four floors of a newly finished luxury complex in four consecutive transactions. Ken Griffin bought 35-38 as raw space. In total, Griffin’s lair is 25,000 square feet of living space

415 E North Water ST PH 5
E North Water St Ph Chicago
Price: $12.95 million

This 9,300-square-foot 2-story penthouse is called the “ultimate Chicago penthouse”

It has a gourmet kitchen, floor-to-ceiling windows, a 2-story lobby with a glass and granite staircase, and $1 million in exotic stone. This mansion has a private indoor basketball/squash court, three 500-gallon saltwater fish tanks, a steam room, and a hot tub with a popup TV. Its five balconies and wraparound porch provide spectacular city views.

159 E Walton Place PH
East Walton Place Michigan Ave Chicago
Price: $13.9 million

This 12,000-square-foot penthouse overlooks Michigan Ave. Magnificent Mile. Vaughn held it until 2016. The penthouse contains 5 bedrooms, 5 bathrooms, a theater, card room, billiard room, private terrace, and 360-degree city views. Monthly condo costs are $12,155. This includes 24-hour concierge service, a gym, and a private party room.

1909 N Orchard St.
N Orchard Street Lincoln Park Chicago
Price: $15.5 million

This Lincoln Park address has 11 condos. Give the developer the globe, and he’ll build a 14,500 square-foot giant mansion. The current plan calls for 6 bedrooms, 6 bathrooms, and open main living space with state-of-the-art finishes and craftsmanship. Indoor and rooftop pools with sundecks and dining room. Don’t worry if you’re interested but require a slightly larger item. The builder may add 28,000 square feet.

11 E. Walton St. In Gold Coast 2014
Price: $16 million

This full-floor condo on the Waldorf Astoria’s 46th floor was one of two units owned by millionaire Ken Griffin. Ken Griffin held it for quite a year and a half before selling it to Jude Reyes, co-chairman of Reyes Holdings, for the same price he paid for it.

56-60 E Chicago Ave.
E Chicago Ave
Price: $19.5 million

This 5,500 square foot mansion in Chicago, needs extensive renovation. Chicago sells the abandoned building. Despite the building’s good position and Victorian appearance, the interior is in serious disrepair.

50 Glade Rd In Glencoe
Chicagos Ritzy North Shore Glade Rd Glencoe
Price: $19.5 million

Some of Chicago’s expensive houses are on Lake Shore Drive and Burling Street.

There are also many luxurious homes in the suburbs, and one of these most expensive areas is Glencoe’s 50 Glade Rd. It is located in Chicago’s ritzy North Shore and features 8 bedrooms and 6.5 baths. It’s 15,800 square feet of living space and was built in 1917.

1516 N Lake Shore Dr.
N Lake Shore Dr
Price: $22 million

Until recently, the International College of Surgeons owned this historic Chicago mansion, but it’s now back on the market as a residential property.

The 12,000 square foot mansion was inspired by French chateaux and completed in 1916. It has stained glass windows, marble stairs, stone walls, intricate molding, herringbone-laid wooden floors, nine fireplaces, and a 10-foot wrought iron double door. The property includes a 2,400-square- foot coach house.

401 N Wabash Ave Unit 89A In River North
North Wabash Avenue Lake Michigan View
Price: $30 million

The highest price per square foot isn’t at 9 W. Walton St. or 1932 N. Burling St.

This is 401 N Wabash Ave, Trump Tower’s $30 million listings. This condo is listed at $2,103 per square foot by Coldwell Banker Realty. With 360-degree views of Lake Michigan and a private elevator, this 14,260-square-foot property has infinite potential. There’s also a 14,000 square foot fitness center and four penthouse-level parking spaces.

1926 N. Burling Street
N Burling Mansion Street Chicago Lincoln Park
Price: $45 million

This Lincoln Park mansion has been the most expensive property in the city since its 2016 listing. The 25,000 square-foot mansion features ornate fountains, a reflecting pool, chandeliers, a grand staircase, marble inlays, and manicured gardens.

How To Live Your Very Own “Expensive” Lifestyle In 2022

If you’re still wondering how anyone can afford these things, here’s a little secret:

You can finance ANYTHING!

Which means most folks aren’t actually paying cash for their expensive house.

They’re financing their purchase over a number of years, and paying a much smaller monthly payment. Even better, in a lot of cases, these people can actually write off this monthly payment as a business expense!

Can you imagine that?

Having the best of everything, living your ideal lifestyle, and getting to do it virtually for free?

Well, now you can!

With Digital Real Estate, you can generate enough monthly passive income to make the monthly payments on your new house, have enough time to actually enjoy it, and maybe even write it off completely!

Even if you’ve never made a single dollar online, Digital Real Estate may just be for you.


1) It’s Flexible: got an hour a day? You can do this. Ready to drop everything else and dive in full time? You can do this. Yes, the more time you put in, the faster you see results. But even with a little time each day, you can move the needle in a Digital Real Estate business.

And because this system is so flexible, you don’t have to constantly be working to make more money. It’s called PASSIVE INCOME because if you stop working, the money doesn’t.

Imagine taking 3 months off to just tour around Europe, rent a cabin in the woods to write a book, hike the Appalachian Trail, or live on the beach and surf all day. This is only possible if you have an income stream that’s not tied to your time.

Jump All In

2) You Own & Control EVERYTHING: Now, when you walk into a room looking and feeling like a boss, your bank account and lifestyle will agree. With Digital Real Estate, you own the assets, which means you have all the power and all the control.

Feeling Blessed

3) Little To No Startup Costs: It’s possible to get into Digital Real Estate with zero dollars upfront. Because, using the strategies outlined in this program, you can get a client to pay you BEFORE spending a penny out of your own pocket…even before you do any work.

Even without getting paid in advance, you can have your first Digital Rental Property up, running, and generating profits for less than $100.

Lance Lead Gen

4) Easy To Duplicate: Ok, here’s the best part: once you have your first Digital Rental Property up and running, you can literally DOUBLE your income with a few clicks, a couple keystrokes, and a single phone call (and you don’t actually need the phone call).

Remember: each Digital Rental Property is worth $500 to $2,000 a month in semi-passive income (over 95% profit). Every time you decide to create another one and increase your income, it gets easier. Because you have more knowledge, more experience, more results, and more momentum.


5) Make Money Helping Real People: With Digital Real Estate, you’re actually helping people by solving your clients’ biggest problem: Small, local businesses need more customers, and with Digital Real Estate, you are unleashing a flood of happy, paying customers for these businesses.

You make money by helping them make money.

Not a big, faceless corporation either…a small business owner who’s using that money to put food on the table for their family, start a college fund for their kids, or take care of a sick parent. Once you see how Digital Real Estate makes a real impact in the lives of real people, you’ll sleep like a baby with a big smile on your face.

Boss of My Own Future

Now, the choice is yours. You could continue looking at articles for the most expensive house in chicago, or you can start taking steps so one day YOU can actually afford them!

At the same time, you’ll join a community of over 2,000 successful students that are living life on their own terms thanks to Digital Real Estate. A consistent, reliable, semi-passive stream of income that doesn’t depend on you or your time to keep producing profits.

All while genuinely helping real people who are grateful and happy to pay for it.

If this sounds more like what you want out of life (or if you just want some nice side income), click here to learn more about Digital Real Estate.


Chicago is also well-known for its numerous and historically significant community areas.

Now that you’re all clued up on the most expensive house in Chicago, have you decided which Chicago neighborhood is best to live in?

Here’s a quick review of the most expensive Chicago:

  1. 1926 N. Burling Street – $45 million
  2. 401 N Wabash Ave Unit 89A In River North – $30 million
  3. 1516 N Lake Shore Dr. – $22 million
  4. 50 Glade Rd In Glencoe – $19.5 million
  5. 56-60 E Chicago Ave. – $19.5 million
  6. 11 E. Walton St. in Gold Coast 2014 – $16 million
  7. 1909 N Orchard St. – $15.5 million
  8. 159 E Walton Place PH – $13.9 million
  9. 415 E North Water ST PH 5 – $12.95 million
  10. 9 W. Walton St. in Gold Coast 2018 – $12.1 million
  11. 11 E Walton St, Unit 5200 – $11.7 million
  12. 199 E. Lake Shore Drive, Unit 10-11E – $11,500,000
  13. 924 N Clark St. – $10.9 million
  14. 68 Locust Rd In Winnetka – 8.75 million
  15. 1432 N. State Parkway – $7,499,000
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