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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$1,599,000

403 N Wabash Avenue 3a, Chicago

3 Beds 3.5 Baths 2,424 SqFt Residential MLS® # 12711390

$1,599,000

↓ $51,000

421 W Melrose Street 18bc, Chicago

4 Beds 4.5 Baths 4,500 SqFt Residential MLS® # 12664065

$1,599,000

↓ $901,000

401 N Wabash Avenue 2346, Chicago

2 Beds 3 Baths 2,100 SqFt Residential MLS® # 12624895

New

$1,595,000

1125 W Monroe Street, Chicago

4 Beds 4.5 Baths 3,300 SqFt Residential MLS® # 12774404

$1,595,000

4941 S Kimbark Avenue, Chicago

5 Beds 3.5 Baths 4,752 SqFt Residential MLS® # 12755676

Open House

$1,595,000

↓ $95,000

840 N Lake Shore Drive 603, Chicago

3 Beds 3.5 Baths 3,198 SqFt Residential

Open House

Sat, Oct 10th, 2026 @ 12pm - 2pm

MLS® # 12698443

$1,595,000

21 E Huron Street 706, Chicago

2 Beds 2 Baths 1,771 SqFt Residential MLS® # 12665424

New Open House

$1,575,000

2237 W Winona Street, Chicago

3 Beds 3.5 Baths 3,068 SqFt Residential

Open House

Sat, Oct 10th, 2026 @ 2pm - 4pm

MLS® # 12765309

New

$1,575,000

3500 N Lake Shore Drive 11c, Chicago

4 Beds 4 Baths 4,000 SqFt Residential MLS® # 12758755

$1,575,000

435 N Michigan Avenue 812, Chicago

1 Bed 1.5 Baths 1,678 SqFt Residential MLS® # 12752294

$1,575,000

401 N Wabash Avenue 81f, Chicago

2 Beds 2.5 Baths 1,952 SqFt Residential MLS® # 12732884

$1,570,000

2742 N Kenmore Avenue, Chicago

4 Beds 0 Baths 0 SqFt Residential Income MLS® # 12623692

New

$1,559,000

6708 N Olympia Avenue, Chicago

4 Beds 4.5 Baths 4,260 SqFt Residential MLS® # 12769326

New

$1,550,000

600 N Lake Shore Drive 3011, Chicago

3 Beds 3 Baths 2,124 SqFt Residential MLS® # 12776874

New

$1,550,000

1940 W Superior Street, Chicago

5 Beds 3.5 Baths 0 SqFt Residential MLS® # 12771539

New

$1,550,000

600 N Lake Shore Drive 1305, Chicago

3 Beds 3.5 Baths 0 SqFt Residential MLS® # 12688483

$1,550,000

224 N Elizabeth Street T2-3b, Chicago

2 Beds 2.5 Baths 0 SqFt Residential MLS® # 12672114

$1,550,000

↓ $65,000

850 N Lake Shore Drive 405, Chicago

2 Beds 3 Baths 2,193 SqFt Residential MLS® # 12586518

New

$1,549,000

1815 W 19th Street, Chicago

7 Beds 0 Baths 0 SqFt Residential Income MLS® # 12762020

$1,549,000

1907 W Berwyn Avenue, Chicago

4 Beds 3.5 Baths 0 SqFt Residential MLS® # 12728858

Open House

$1,549,000

↓ $50,000

363 E Wacker Drive 5105, Chicago

2 Beds 2 Baths 0 SqFt Residential

Open House

Sun, Oct 11th, 2026 @ 12pm - 2pm

MLS® # 12622718

$1,525,000

161 E Chicago Avenue 49a, Chicago

3 Beds 2.5 Baths 2,510 SqFt Residential MLS® # 12683042

New

$1,525,000

1160 S Michigan Avenue 4101, Chicago

3 Beds 2.5 Baths 3,483 SqFt Residential MLS® # 12682842

$1,500,000

55 E Erie Street 4503, Chicago

3 Beds 2.5 Baths 2,300 SqFt Residential MLS® # 12757426

$1,500,000

2326 W Erie Street, Chicago

5 Beds 3.5 Baths 0 SqFt Residential MLS® # 12739704

$1,500,000

3414 N Oakley Avenue, Chicago

4 Beds 3.5 Baths 3,260 SqFt Residential MLS® # 12734355

$1,500,000

1769 W Olive Avenue, Chicago

5 Beds 3.5 Baths 4,000 SqFt Residential MLS® # 12727324

New

$1,499,900

2640 N Bosworth Avenue Phs, Chicago

3 Beds 2.5 Baths 2,380 SqFt Residential MLS® # 12768902

New

$1,499,900

950 N Michigan Avenue 3103, Chicago

3 Beds 3.5 Baths 2,430 SqFt Residential MLS® # 12753829

New

$1,499,000

600 N Lake Shore Drive 4211, Chicago

3 Beds 3 Baths 2,124 SqFt Residential MLS® # 12760284

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