The 20 Most Expensive Homes in Chicago

If you have plenty of money to spend, you definitely have plenty of housing options to choose from in a city like Chicago. In fact, there are currently more than 1,000 homes on the market with a listing price well over $1 million in Chicago alone. As a result, it shouldn’t be too hard to believe that several Chicago properties, both single-family residences and condos, are nothing short of spectacular. The homes on this list certainly fit the bill.

Whether it’s in the suburbs or in a fancy high rise that looks like something a Manhattan resident would buy, there’s usually something for everyone in the Windy City.  But only a select few can distinguish themselves from the rest by being the priciest.

Here are the 20 most expensive homes in Chicago.

363 E Wacker Dr. #8501 – $10.369 million

Let me start by saying that even if you buy this 6,521 sq. ft. condo today, you’ll have to wait until 2020 to move in. However, it may be well worth the wait as it is being built. It will sit atop Chicago’s newest luxury building, Sky 360 Residences, where absolutely no detail has been overlooked. The condo will include 5 bedrooms, 5 bathrooms, 11’ ceilings with recessed lighting, motorized window treatments covering the floor-to-ceiling windows, stone walls, heated floors, and top-of-the-line fixtures and appliances. The building will offer plenty of amenities, such as an indoor and outdoor pool, hot tub, enclosed dog exercise area, fitness room, and a private win tasting and storage room. Of course, these luxury amenities are going to cost you. The monthly condo fee is set to be $5,638.

924 N Clark St. – $10.9 million

Built as a substation in 1916, this property has undergone a huge transformation to become a 15,000 sq. ft. home with 6 bedrooms and 9 bathrooms spread over 4 levels. The home includes everything from a chef’s kitchen and wine cellar to a rooftop deck, greenhouse, rec room, and luxury bathrooms with huge tubs, separate steam showers, and a meditation room. Also on the property is a pool house that creates an enclosed courtyard complete with pool, fireplace, plenty of green space, and a huge patio for entertaining. At one point, this house was listed for $13.9 million, which makes the current asking price a bargain


1547 Dearborn Parkway – $11 million

Situated on a highly coveted oversized lot, this 18,950 sq. ft. Victorian limestone mansion was at one point on the market for $18.75 million. (There is not a comparable property on the market, making it hard to confirm the home’s value, which ranges from $18 million to $11 million depending on where you look.) Built in 1891, the 12-bedroom, 13-bathroom house was serious disrepair when purchased by the current owner, Ann Lurie. Since then, a huge amount of work has gone into restoring it, while paying careful attention to preserving its original built-ins and architectural finishes. Additionally, a huge sunroom was added, along with a basement that includes a billiards room and lounge.

11 E Walton St, Unit 5200 – $11.7 million

Built in 2009 and last sold in 2016, this custom built  4-bedroom, 4 ½-bathroom condo takes up the Waldorf Astoria’s entire 52nd floor, where the floor-to-ceiling windows and multiple terraces provide unrivalled views of the city. Inside, it’s easy to see that no expense was spared, thanks to the glass enclosed wine cellar, bar, home theater, and master suite complete with an over-the-top bathroom and closet that is significantly larger than most living rooms in your average home. And, being a multi-million dollar property, there’s a private, indoor pool . As an added bonus, residents get to enjoy all the luxury amenities associated with condo living, including concierge services, 24-hour room service courtesy of the hotel, and valet parking. Of course, the monthly HOA fee is $5,979.

800 N Michigan Ave. #60PHN – $12 million

This 4,000 sq. ft. Park Hyatt penthouse is nothing short of spectacular. Custom designed and built in 2000, the 2-bedroom, 2.5 –bathroom Crestron smarthome includes 12 ft. ceilings, a state-of-the-art kitchen, heated marble floors, private elevator access, huge windows, and multiple balconies that make it easy to enjoy the indescribable views of Lake Michigan. It features only the finest fixtures and appliances, as well as custom millwork. Plenty of amenities are available, including all of the Park Hyatt’s services, a health club, indoor pool, concierge services, and more. Best of all, the monthly condo fees are just $3139 and the condo is currently on the market, meaning you could make it your own.

1336 N State Pkwy. – $12.5 million

Built in 1897, this 5-bedroom, 7-bathroom home has been completely renovated using only the finest materials to ensure it maintains its original charm, yet offers all of today’s modern conveniences. Spanning 9,000 sq. ft. and four levels, the Georgian-style home features a dramatic entryway with a gorgeous spiral staircase, cathedral ceilings with skylights, five fireplaces, and intricate molding. It includes terraces on every level and the rooftop, a home gym, home theater, library, garden room, separate catering kitchen, billiards room, and an attached garage.

1443 N Astor St. – $12.59 million

Built in 1891, this 11,000 sq. ft. home is a unique mixture of old and new. The old refers to expertly restored original light fixtures and detailed millwork, nine fireplaces, and two dramatic staircases, while the new refers to the gourmet kitchen, 12 spa-like bathrooms, skylights, and elevator that make it easy to move between the five levels. The bottom floor is home to a large movie theater, wine cellar and separate tasting room, fitness center, and spa. There are tons of extra touches in this house, such as the leaded glass window alongside the main staircase, handcrafted white oak floors with a brass and stone inlay, and custom cabinets with hand-tooled wood details.

401 N. Wabash Ave #87A – $12.7 million

Yet another penthouse with a breathtaking view, this 6,850 sq. ft. unit is situated on the 87th floor of the Trump Tower. It features huge floor-to-ceiling windows, 16 ft. ceilings, handcrafted hardwood fixtures, rift sawn oak floors, custom stonework, fabric wall coverings, and exquisite build-ins. A top-of-the-line kitchen with a butler’s pantry and wine cellar and open floorplan make it perfect for entertaining. It almost goes without saying that the amenities it comes with are nothing short of 5-star and include an onsite world-class spa and Michelin-rated French restaurant. While the monthly condo fee is $8,851, the asking price did just drop to $9.95 million, meaning your mortgage won’t be quite as high.

415 E North Water ST PH#5 – $12.95 million

Touted as the “ultimate Chicago penthouse, “ this 9,300 sq. ft. 2-story penthouse has everything you could possibly want in a house and more. It features a gourmet kitchen, floor-to-ceiling windows, a magnificent 2-story foyer with a floating glass and granite staircase, and over $1 million worth of exotic stone. In addition to the amenities that come with living in Riverview Condominiums, this house includes a private indoor basketball/ squash court, three 500-gallon saltwater fish tanks, steam room, and hot tub with a popup TV. It offers panoramic views of the city, which can easily be seen from one of the five balconies or the wraparound porch. It’s currently on the market and recently had the asking price reduced to $8.990 million, if you’re interested.

9 W Walton St. Unit 3500 – $12.95 million

Located in one of Chicago’s newest luxury buildings, No. 9 Walton, this 5-bedroom, 5 ½-bathroom penthouse offers 7100 sq. ft. of indoor living space and 1100 sq. ft. of private outdoor living space. It’s not quite finished yet, giving any interested buyers the opportunity to customize the interior. (There is an offer pending.) The building, of course, offers 5-star amenities, including a doorman, valet parking, indoor pool, fitness center, and much more. Based on the plans submitted by the builder, it looks like this unit may include a private swimming pool when it is completed in spring 2018.

1819 N. Howe St. – $13 million

Here’s the thing. This home hasn’t actually been built, but the plans have been loosely drawn up by one of Chicago’s most esteemed builders, Environs Development. The plans include a 13,000 sq. ft. home with 7 bedrooms, 7 ½ bathrooms, a 6-car heated garage, and a gorgeous rooftop deck. Based on the information available, it appears that someone will have to shell out the money for the house before the builders will break grown. On the plus side, whoever buys it will have the opportunity to customize everything from the style and floorplan to all the finishes.

1955 N Burling St. – $13.345 million

Although this gorgeous 20,000 sq. ft. brick and limestone mansion had an asking price of $18.75 million, the lucky owners were able to purchase it for a mere $13.345 million in December 2015. The home, which sits on 5 city lots, was built in 2004 and includes 7 bedrooms and 9 full bathrooms, as well as a 6-car garage and all the other necessities that come with living in a multi-million dollar home, such as a gourmet kitchen, custom home theater, billiards room, and spectacular indoor pool and hot tub. The outside is just as amazing, thanks to the multiple patios, dining area with a huge fireplace, sculptures, and meticulously kept gardens. By the way, there are also 2 detached guest houses on the property.

159 E Walton Place PH – $13.9 million

Overlooking Michigan Avenue’s Magnificent Mile, this 12,000 sq. ft. triplex penthouse is located in the prestigious Palmolive Building and was owned by Vince Vaughn until 2016. It’s considered one of Chicago’s best examples of art deco architecture. In addition to 5 huge bedrooms and 5 bathrooms, the penthouse features a screening room, card room, billiard room, several private terraces, and an outdoor living space with 360-degree views of the city. On a side note, the monthly condo fee is an outrageous $12,155. This gets you 24-hour concierge service, as well as access to an exercise facility and a private party room that you probably don’t need if you happen to live in this particular condo.

1909 N Orchard St. – $15.5 million

Currently a building with 11 condos sits at this coveted Lincoln Park address. However, all you have to do is give the developer the world and he’ll tear it down and replace it with this 14,500 sq. ft. mega mansion. Although it can be customized to the buyer’s specifications, the current plan calls for 6 bedrooms, 6 bathrooms, and an open main living space complete with state-of-the-art kitchen and only the finest finishes and craftsmanship. An indoor pool is included, as is a rooftop pool with a sundeck and outdoor dining area. If you are interested, but need something a tad bigger, don’t worry. The developer can expand the home to as much as 28,000 sq. ft.

11 E. Walton St. – $16 million

Situated on the 46th floor of the Waldorf Astoria tower, very little is known about this full-floor condo that was last sold in December 2015 by Ken Griffin, a billionaire hedge fund manager who founded Citadel. He had only purchased the condo a year earlier for the same price. The listing was never made public, so interior details are unknown.

401 N. Wabash Ave #89A – $17 million

One of the western hemisphere’s highest residences, this 14,260 sq. ft. penthouse sits on the 89th floor of Trump Towers. Despite paying $17 million for the property in 2014, the owner Sanjay Shah reported that he expected to spend an additional $15 million to finish up the 5-bedroom, 7-bathroom home. (Today, there’s no telling just how much it is worth.) There’s no information available regarding what Shah did to the home, but we do know that he gets to enjoy all the Trump Towers amenities, including 24-hour room service, a pool, security, and more.

800 N. Michigan Ave. 65PH – $18.75 million

This condo sold for $18.75 in May 2015 and is believed to have been purchased by “Star Wars” creator George Lucas, who already owned a 48th floor condo in the prestigious Park Tower building Surprisingly little information is available about the unit, though we do know it sits on the 65th floor and boasts breathtaking views, thanks to the floor-to-ceiling windows.

56-60 E Chicago Ave. – $19.5 million

Located in the historical Amanda Apartments, this 5,500 sq. ft. residential property is need of extensive renovation, as are all the other properties (25 residential and 3 commercial) for sale in the building, which was built in 1891 and is home to Chicago’s second oldest elevator. It appears that the entire building has been left abandoned and is currently being sold by the City of Chicago. Unfortunately, there is no specific interior information or photos, but you can almost be certain that it is serious disrepair, despite the huge price tag, which is largely the result of the building’s prime location and its unique Victorian exterior.

1516 N Lake Shore Dr. – $22 million

Until recently, this historic Chicago mansion was owned by the International College of Surgeons, but now it is back on the market as a residential property and looking for a new owner who isn’t afraid of renovations. Inspired by French chateaus, the 12,000 sq. ft. home was built in 1916 and is listed on the National Register of Historic Places. It still maintains numerous classic details, including stained glass windows, marble staircases, stone walls, detailed molding, herringbone laid hardwood flowers, nine fireplaces, and a 10 ft. wrought iron double door at the entrance. A 2,400 sq. ft. coach house is included on the property.

1932 N Burling St. – $50 million

With a price tag that is more than double the second most expensive home in Chicago, this 25,000 sq. ft. mansion is in a class all its own. Custom-built by the current owners in 2010 on 8 city lots on what many consider to be the Chicago’s finest street, the home’s manicured grounds include a reflecting pool, multiple fountains, and a hand-forged antique pavilion provide plenty of outdoor privacy in spite of all the city’s hustle and bustle. Inside, the 6-bedroom, 7-bathroom home includes a spectacular foyer complete with spiral staircase and intricately detailed molding and ceiling tiles, as well as a gourmet kitchen, music room, craft room, wine cellar with separate tasting room, gallery areas for displaying priceless works of art, and way too much more to name.

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