Chicago Real Estate News & Neighborhood Notes

Since the record breaking sale of the penthouse at Trump Tower Chicago, it’s been a little while since we’ve checked in on some of downtown Chicago’s most expensive properties on the market.

As of today, just 10 listings are currently active on the Chicago real estate market for $10 million and over—appropriately enough—and as you can see below, some like the single-family mansion at 1547 N. Dearborn and the penthouse at 189 E. Lake Shore Drive are relatively familiar to those of us working in the industry every day, while others like the 7,100 square foot, full-floor condo at 9 W. Walton only just recently hit the MLS®.

Despite the luxury market being extremely hot right now in Chicago, when dealing with this sort of price level, it’s of course common for these and other ultra high-end properties to sit on the market a bit longer. But given the appeal, desirability, and overall spectacular nature that basically all of Chicago’s most expensive homes and condos offer, you never know when somebody might swoop in and make that life-changing investment.

For more information about luxury real estate in Downtown Chicago or to schedule a private showing for one the city’s elite property listings, contact one of our luxury home experts today at (312) 280-9600!

$10+ Million MLS® Listings Available in Chicago Right Now

Search $10+ Million MLS® Listings in Chicago, Over $1,000,000

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• Over $1,000,000

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New Open House

$2,395,000

616 W Willow Street, Chicago

5 Beds 3.5 Baths 0 SqFt Residential

Open House

Sat, Oct 10th, 2026 @ 11am - 1pm

MLS® # 12779844

$2,395,000

↓ $100,000

840 N Lake Shore Drive 201, Chicago

3 Beds 3.5 Baths 3,985 SqFt Residential MLS® # 12577539

New

$2,375,000

77 E Walton Street 24a, Chicago

3 Beds 3.5 Baths 3,834 SqFt Residential MLS® # 12776993

New

$2,375,000

363 E Wacker Drive 2106, Chicago

3 Beds 2.5 Baths 2,539 SqFt Residential MLS® # 12774343

Open House

$2,350,000

1620 W Pierce Avenue, Chicago

6 Beds 6 Baths 4,716 SqFt Residential

Open House

Sat, Oct 10th, 2026 @ 10am - 12pm

MLS® # 12700481

New

$2,350,000

3541 N Paulina Street, Chicago

3 Beds 4.5 Baths 4,100 SqFt Residential MLS® # 12698952

$2,350,000

↓ $100,000

401 N Wabash Avenue 86d, Chicago

3 Beds 3.5 Baths 3,000 SqFt Residential MLS® # 12690510

$2,350,000

333 W Hubbard Street 1006, Chicago

3 Beds 4 Baths 5,020 SqFt Residential MLS® # 12664153

$2,350,000

↓ $150,000

401 N Wabash Avenue 59a, Chicago

3 Beds 3.5 Baths 3,080 SqFt Residential MLS® # 12646153

$2,349,000

363 E Wacker Drive 6403, Chicago

3 Beds 3 Baths 2,333 SqFt Residential MLS® # 12557236

$2,325,000

↓ $46,500

4900 S Kimbark Avenue, Chicago

5 Beds 5.5 Baths 6,700 SqFt Residential MLS® # 12711888

$2,323,000

363 E Wacker Drive 6303, Chicago

3 Beds 3 Baths 2,334 SqFt Residential MLS® # 12557243

$2,300,000

1934 N Cleveland Avenue, Chicago

4 Beds 3.5 Baths 4,798 SqFt Residential MLS® # 12728875

New

$2,299,500

220 S Green Street 4s, Chicago

4 Beds 4 Baths 3,878 SqFt Residential MLS® # 12778065

$2,299,000

453 W Briar Place 3w, Chicago

3 Beds 3.5 Baths 0 SqFt Residential MLS® # 12575316

$2,295,000

1842 N Wood Street, Chicago

3 Beds 3.5 Baths 4,200 SqFt Residential MLS® # 12738388

$2,295,000

2029 N Hoyne Avenue, Chicago

4 Beds 3.5 Baths 3,400 SqFt Residential MLS® # 12732201

$2,295,000

363 E Wacker Drive 1906, Chicago

3 Beds 2.5 Baths 2,499 SqFt Residential MLS® # 12729205

New

$2,295,000

4901 S Kimbark Avenue, Chicago

8 Beds 5.5 Baths 6,500 SqFt Residential MLS® # 12702363

New

$2,280,000

363 E Wacker Drive 4209, Chicago

3 Beds 3.5 Baths 2,562 SqFt Residential MLS® # 12753493

New

$2,275,000

111 E Chestnut Street Ph-ab, Chicago

3 Beds 3 Baths 2,600 SqFt Residential MLS® # 12753365

New

$2,250,000

415 E North Water Street 2805, Chicago

3 Beds 3 Baths 4,705 SqFt Residential MLS® # 12744448

$2,250,000

↓ $125,000

4442 N Greenview Avenue, Chicago

4 Beds 4.5 Baths 4,560 SqFt Residential MLS® # 12685898

$2,250,000

403 N Wabash Avenue 12b, Chicago

3 Beds 3.5 Baths 2,517 SqFt Residential MLS® # 12561047

New Open House

$2,249,999

3041 N Leavitt Street, Chicago

6 Beds 5.5 Baths 0 SqFt Residential

Open House

Sun, Oct 11th, 2026 @ 12pm - 1:30pm

MLS® # 12781609

$2,225,000

55 W Delaware Place 1120, Chicago

3 Beds 4.5 Baths 5,500 SqFt Residential MLS® # 12741185

New

$2,200,000

925 W Wolfram Street, Chicago

3 Beds 2.5 Baths 2,270 SqFt Residential MLS® # 12776866

New

$2,200,000

1839 N Dayton Street Ph-01, Chicago

3 Beds 2 Baths 0 SqFt Residential MLS® # 12774822

New

$2,200,000

363 E Wacker Drive 1506, Chicago

3 Beds 2.5 Baths 2,453 SqFt Residential MLS® # 12759010

New

$2,199,800

1220 N Damen Avenue, Chicago

4 Beds 4.5 Baths 5,000 SqFt Residential MLS® # 12718791

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• Luxury Chicago Real Estate (36)
• Luxury Chicago Condos (14)