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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$2,000,000

1839 N Dayton Street 101, Chicago

3 Beds 2.5 Baths 0 SqFt Residential MLS® # 12766840

$2,000,000

2426 N Burling Street, Chicago

3 Beds 3.5 Baths 3,000 SqFt Residential MLS® # 12758898

$2,000,000

2127 W Huron Street, Chicago

5 Beds 5 Baths 4,100 SqFt Residential MLS® # 12505447

$1,999,000

1962 W Wilson Avenue, Chicago

5 Beds 4.5 Baths 4,000 SqFt Residential MLS® # 12736994

$1,999,000

2156 N Claremont Street, Chicago

6 Beds 5.5 Baths 0 SqFt Residential MLS® # 12681274

$1,999,000

1619 W Summerdale Avenue, Chicago

6 Beds 5 Baths 4,200 SqFt Residential MLS® # 12649531

$1,999,000

↓ $73,000

850 N Lake Shore Drive 205, Chicago

3 Beds 2.5 Baths 3,794 SqFt Residential MLS® # 12479877

New

$1,995,000

257 E Delaware Place 10ab, Chicago

4 Beds 4.5 Baths 4,000 SqFt Residential MLS® # 12774015

Open House

$1,995,000

1034 N La Salle Drive, Chicago

5 Beds 3.5 Baths 4,279 SqFt Residential

Open House

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

MLS® # 12765008

Open House

$1,995,000

119 W Delaware Place, Chicago

4 Beds 4.5 Baths 4,400 SqFt Residential

Open House

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

MLS® # 12750868

New

$1,995,000

152 W Huron Street 4, Chicago

3 Beds 2.5 Baths 4,300 SqFt Residential MLS® # 12736423

$1,995,000

2644 N Lakewood Avenue 2n, Chicago

4 Beds 3.5 Baths 0 SqFt Residential MLS® # 12731733

$1,995,000

2452 N Janssen Avenue, Chicago

5 Beds 3.5 Baths 4,000 SqFt Residential MLS® # 12709204

$1,995,000

180 E Pearson Street 4801, Chicago

3 Beds 2.5 Baths 2,754 SqFt Residential MLS® # 12674616

$1,990,000

2214 W Oakdale Avenue, Chicago

6 Beds 4.5 Baths 4,500 SqFt Residential MLS® # 12756141

$1,990,000

840 N Lake Shore Drive 1803, Chicago

3 Beds 3.5 Baths 3,200 SqFt Residential MLS® # 12722568

$1,990,000

↓ $110,000

401 N Wabash Avenue 60e, Chicago

2 Beds 3 Baths 2,754 SqFt Residential MLS® # 12671939

Open House

$1,985,000

1934 N Halsted Street 1, Chicago

4 Beds 3.5 Baths 0 SqFt Residential

Open House

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

MLS® # 12619024

$1,979,000

363 E Wacker Drive 6805, Chicago

3 Beds 3 Baths 1,942 SqFt Residential MLS® # 12557178

$1,975,000

4844 N Hermitage Avenue, Chicago

6 Beds 4.5 Baths 4,800 SqFt Residential MLS® # 12756287

New

$1,975,000

2331 N Talman Avenue, Chicago

3 Beds 3.5 Baths 3,327 SqFt Residential MLS® # 12674650

Open House

$1,975,000

1935 N Mohawk Street 1s, Chicago

4 Beds 4 Baths 0 SqFt Residential

Open House

Sat, Oct 10th, 2026 @ 1pm - 2:30pm

MLS® # 12597724

New

$1,950,000

450 E Waterside Drive 3309, Chicago

3 Beds 3 Baths 2,714 SqFt Residential MLS® # 12775282

Open House

$1,950,000

1935 N Mohawk Street 3n, Chicago

3 Beds 3 Baths 0 SqFt Residential

Open House

Sat, Oct 10th, 2026 @ 1pm - 2:30pm

MLS® # 12745505

$1,950,000

118 E Erie Street 35g, Chicago

2 Beds 2.5 Baths 2,874 SqFt Residential MLS® # 12596294

New

$1,949,900

4400 S Oakenwald Avenue, Chicago

12 Beds 0 Baths 0 SqFt Residential Income MLS® # 12774811

New

$1,949,500

1940 W Wabansia Avenue, Chicago

4 Beds 3.5 Baths 3,800 SqFt Residential MLS® # 12768858

New

$1,949,000

2026 N Orleans Street Phs, Chicago

3 Beds 3.5 Baths 0 SqFt Residential MLS® # 12771422

New

$1,900,000

200 N Dearborn Street 4700, Chicago

3 Beds 3 Baths 2,957 SqFt Residential MLS® # 12772801

$1,900,000

200 W Grand Avenue 2700, Chicago

3 Beds 3.5 Baths 4,150 SqFt Residential MLS® # 12760625

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