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

• All Listings
• Over $1,000,000

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New

$3,375,000

1842 North Wolcott Avenue, Chicago, 60622

5 Beds 7 Baths 5,700 SqFt Residential MLS® # 12544187

New

$3,499,000

2034 West Sunnyside Avenue, Chicago, 60625

4 Beds 7 Baths 5,600 SqFt Residential MLS® # 12544149

New

$5,750,000

1019 North Wolcott Avenue, Chicago, 60622

6 Beds 8 Baths 9,740 SqFt Residential MLS® # 12542422

New

$3,750,000

446 West Huron Street, Chicago, 60654

6 Beds 9 Baths 0 SqFt Residential MLS® # 12541693

New

$3,250,000

3711 North Magnolia Avenue, Chicago, 60613

6 Beds 7 Baths 5,539 SqFt Residential MLS® # 12540531

New Contingent

$3,895,000

1520 North Dearborn Parkway, Chicago, 60610

5 Beds 5 Baths 7,065 SqFt Residential MLS® # 12533469

$4,400,000

2119 North Seminary Avenue, Chicago, 60614

6 Beds 7 Baths 5,200 SqFt Residential MLS® # 12536741

$5,250,000

3523 North Bosworth Avenue, Chicago, 60657

7 Beds 9 Baths 6,700 SqFt Residential MLS® # 12440024

$3,395,000

1401 North Astor Street, Chicago, 60610

5 Beds 7 Baths 5,500 SqFt Residential MLS® # 12535746

Contingent

$3,500,000

3336 North Oakley Avenue, Chicago, 60618

8 Beds 7 Baths 0 SqFt Residential MLS® # 12529088

$4,475,000

1434 North Dearborn Street, Chicago, 60610

5 Beds 7 Baths 6,815 SqFt Residential MLS® # 12445304

Contingent

$4,950,000

457 West Deming Place, Chicago, 60614

5 Beds 6 Baths 5,000 SqFt Residential MLS® # 12505890

$3,800,000

2209 North Seminary Avenue, Chicago, 60614

5 Beds 7 Baths 5,918 SqFt Residential MLS® # 12507680

$4,995,000

1407 North Hoyne Avenue, Chicago, 60622

5 Beds 7 Baths 8,250 SqFt Residential MLS® # 12505482

$3,658,000

907-909 West Webster Avenue, Chicago, 60614

7 Beds 6 Baths 7,404 SqFt Residential MLS® # 12493988

$3,595,000

1837 North Fremont Street, Chicago, 60614

5 Beds 4 Baths 4,662 SqFt Residential MLS® # 12494842

$3,995,000

536 West Barry Avenue, Chicago, 60657

5 Beds 6 Baths 10,580 SqFt Residential MLS® # 12463373

Contingent

$4,000,000

2719 North Dayton Avenue, Chicago, 60614

6 Beds 7 Baths 5,200 SqFt Residential MLS® # 12489324

Contingent

$3,250,000

2661 North Dayton Street, Chicago, 60614

6 Beds 5 Baths 5,850 SqFt Residential MLS® # 12484962

$7,995,000

1878 North Orchard Street, Chicago, 60614

5 Beds 8 Baths 9,512 SqFt Residential MLS® # 12481062

$6,950,000

1865 North Burling Street, Chicago, 60614

4 Beds 7 Baths 6,000 SqFt Residential MLS® # 12473105

Contingent

$3,100,000

5638 South Woodlawn Avenue, Chicago, 60637

6 Beds 9 Baths 8,000 SqFt Residential MLS® # 12446282

$6,500,000

↓ $400,000

1438 North Dearborn Street, Chicago, 60610

5 Beds 8 Baths 0 SqFt Residential MLS® # 12379566

$3,300,000

1823 North Bissell Street, Chicago, 60614

6 Beds 6 Baths 0 SqFt Residential MLS® # 12446176

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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.