Most Expensive Homes in Chicago IL

Interested in Chicago's most expensive homes for sale? If a luxury condo isn't your thing, you've probably noticed quite a few amazing single-family homes listed on the market at any given time. Neighborhoods like Lakeview, Roscoe Village, and Lincoln Park are where you'll find some of the city's largest and most expensive homes, but multi-million dollar homes and estates can also be found all over the city, as you'll see below. 

If you would like more information on any of the most expensive homes for sale in Chicago, our team can provide with with additional details, up-to-the-minute market data, disclosures associated with a property, and also a list of recently sold luxury homes to help you better determine an appropriate offer. And as always, we also encourage all luxury home buyers in Chicago to register for a free account, allowing you to stay one-step ahead of other home buyers considering a luxury home in the Chicago area. 

Search Chicago's Most Expensive Homes For Sale

Sort by:
New
338 West Oakdale Avenue, Chicago, 60657

$3,245,000

338 West Oakdale Avenue, Chicago, 60657

7 Beds 7 Baths 7,650 SqFt Residential MLS® # 12108972

Midwest Real Estate Data LLC Logo

New
1444 West Cuyler Avenue, Chicago, 60613

$3,400,000

1444 West Cuyler Avenue, Chicago, 60613

6 Beds 7 Baths 5,000 SqFt Residential MLS® # 12078803

Midwest Real Estate Data LLC Logo

New
111 East Bellevue Place, Chicago, 60611

$3,495,000

111 East Bellevue Place, Chicago, 60611

3 Beds 4 Baths 5,460 SqFt Residential MLS® # 12102315

Midwest Real Estate Data LLC Logo

New
3533 North Greenview Avenue, Chicago, 60657

$3,800,000

3533 North Greenview Avenue, Chicago, 60657

6 Beds 5 Baths 6,600 SqFt Residential MLS® # 12104294

Midwest Real Estate Data LLC Logo

2015 West Shakespeare Avenue, Chicago, 60647

$3,295,000

2015 West Shakespeare Avenue, Chicago, 60647

5 Beds 5 Baths 6,139 SqFt Residential MLS® # 12096530

Midwest Real Estate Data LLC Logo

53 East Bellevue Place, Chicago, 60611

$4,995,000

53 East Bellevue Place, Chicago, 60611

4 Beds 6 Baths 6,500 SqFt Residential MLS® # 12092144

Midwest Real Estate Data LLC Logo

3504 North Janssen Avenue, Chicago, 60657

$4,400,000

3504 North Janssen Avenue, Chicago, 60657

7 Beds 8 Baths 6,965 SqFt Residential MLS® # 12092351

Midwest Real Estate Data LLC Logo

1540 North Dearborn Parkway, Chicago, 60610

$5,950,000

1540 North Dearborn Parkway, Chicago, 60610

4 Beds 9 Baths 7,600 SqFt Residential MLS® # 11976280

Midwest Real Estate Data LLC Logo

Contingent
1806 North Wood Street, Chicago, 60622

$3,500,000

1806 North Wood Street, Chicago, 60622

6 Beds 6 Baths 8,960 SqFt Residential MLS® # 12088947

Midwest Real Estate Data LLC Logo

325 West Wellington Avenue, Chicago, 60657

$4,995,000

325 West Wellington Avenue, Chicago, 60657

11 Beds 10 Baths 14,000 SqFt Residential MLS® # 12076026

Midwest Real Estate Data LLC Logo

1308 North Astor Street, Chicago, 60610

$3,395,000

1308 North Astor Street, Chicago, 60610

4 Beds 5 Baths 4,717 SqFt Residential MLS® # 12078801

Midwest Real Estate Data LLC Logo

537 West Grant Place, Chicago, 60614

$3,500,000

↓ $195,000

537 West Grant Place, Chicago, 60614

5 Beds 6 Baths 5,500 SqFt Residential MLS® # 12084973

Midwest Real Estate Data LLC Logo

401 West Dickens Avenue, Chicago, 60614

$6,590,000

401 West Dickens Avenue, Chicago, 60614

4 Beds 7 Baths 7,252 SqFt Residential MLS® # 12084770

Midwest Real Estate Data LLC Logo

1432 North Astor Street, Chicago, 60610

$3,300,000

1432 North Astor Street, Chicago, 60610

5 Beds 6 Baths 6,300 SqFt Residential MLS® # 12079728

Midwest Real Estate Data LLC Logo

Contingent
2010 North Mohawk Street, Chicago, 60614

$3,450,000

2010 North Mohawk Street, Chicago, 60614

5 Beds 8 Baths 7,176 SqFt Residential MLS® # 12074350

Midwest Real Estate Data LLC Logo

861 North Lasalle Street, Chicago, 60610

$3,249,995

861 North Lasalle Street, Chicago, 60610

5 Beds 7 Baths 7,480 SqFt Residential MLS® # 12079723

Midwest Real Estate Data LLC Logo

3623 North Wayne Avenue, Chicago, 60613

$3,750,000

3623 North Wayne Avenue, Chicago, 60613

6 Beds 7 Baths 7,000 SqFt Residential MLS® # 12075104

Midwest Real Estate Data LLC Logo

1502 North Dearborn Parkway, Chicago, 60610

$3,499,999

1502 North Dearborn Parkway, Chicago, 60610

4 Beds 6 Baths 5,660 SqFt Residential MLS® # 12077470

Midwest Real Estate Data LLC Logo

2020 North Dayton Street, Chicago, 60614

$3,299,000

2020 North Dayton Street, Chicago, 60614

6 Beds 6 Baths 5,200 SqFt Residential MLS® # 12074262

Midwest Real Estate Data LLC Logo

229 West Eugenie Street, Chicago, 60614

$5,994,400

229 West Eugenie Street, Chicago, 60614

5 Beds 6 Baths 7,528 SqFt Residential MLS® # 12073203

Midwest Real Estate Data LLC Logo

1848 North Howe Street, Chicago, 60614

$4,780,000

1848 North Howe Street, Chicago, 60614

5 Beds 7 Baths 6,450 SqFt Residential MLS® # 12072917

Midwest Real Estate Data LLC Logo

1805 North Sedgwick Street, Chicago, 60614

$3,550,000

1805 North Sedgwick Street, Chicago, 60614

5 Beds 7 Baths 6,000 SqFt Residential MLS® # 12068952

Midwest Real Estate Data LLC Logo

77 East Cedar Street, Chicago, 60611

$4,499,000

77 East Cedar Street, Chicago, 60611

4 Beds 6 Baths 6,000 SqFt Residential MLS® # 12070227

Midwest Real Estate Data LLC Logo

2015 North Dayton Street, Chicago, 60614

$5,000,000

2015 North Dayton Street, Chicago, 60614

7 Beds 8 Baths 7,000 SqFt Residential MLS® # 12063481

Midwest Real Estate Data LLC Logo

Are you planning to buy or sell a home or condo in Chicago? Contact the Chicago Condo Finder Team, Chicago's local condo experts, for help navigating the current market conditions. Call or text (312) 953-0961 now to schedule a showing for a unit you'd like to preview!

Contact Us For more Info About Luxury Homes & Real Estate in Chicago

Chicago is home to a number of world-class luxury homes and condominiums. To schedule a private tour of your preferred properties, please contact our team of real estate specialists.