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

• All Listings
• Over $1,000,000

Show Map

Save Search

Sort by:

Price, high to low

$2,850,000

900 W Washington Boulevard 202, Chicago

4 Beds 4.5 Baths 3,660 SqFt Residential MLS® # 12706853

Open House

$2,850,000

224 N Elizabeth Street T2-7a, Chicago

3 Beds 3.5 Baths 0 SqFt Residential

Open House

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

MLS® # 12672552

$2,800,000

2468 N Orchard Street 3, Chicago

4 Beds 4.5 Baths 2,900 SqFt Residential MLS® # 12726602

$2,789,000

↓ $210,000

435 N Michigan Avenue 2004, Chicago

3 Beds 3.5 Baths 3,505 SqFt Residential MLS® # 12725595

New

$2,775,000

333 W Hubbard Street 701, Chicago

3 Beds 3.5 Baths 3,200 SqFt Residential MLS® # 12757501

$2,750,000

↓ $149,000

2733 N Pulaski Road, Chicago

4 Beds 3.5 Baths 7,000 SqFt Residential MLS® # 12590864

New

$2,749,000

652 W Sheridan Road, Chicago

5 Beds 4.5 Baths 6,806 SqFt Residential MLS® # 12767765

New

$2,699,000

2429 N Rockwell Street, Chicago

4 Beds 5 Baths 0 SqFt Residential MLS® # 12633471

$2,690,000

↓ $110,000

401 N Wabash Avenue 43a, Chicago

3 Beds 4.5 Baths 3,948 SqFt Residential MLS® # 12624205

New

$2,675,000

2730 N Hartland Court, Chicago

6 Beds 5.5 Baths 6,300 SqFt Residential MLS® # 12766612

$2,675,000

45 E Cedar Street 200, Chicago

3 Beds 3.5 Baths 3,000 SqFt Residential MLS® # 12331403

$2,649,000

↓ $50,000

3714 N Claremont Avenue, Chicago

4 Beds 4.5 Baths 5,000 SqFt Residential MLS® # 12769566

$2,600,000

3738 N Leavitt Street, Chicago

4 Beds 4.5 Baths 4,600 SqFt Residential MLS® # 12639647

$2,599,000

2039 N Humboldt Boulevard, Chicago

4 Beds 3.5 Baths 5,046 SqFt Residential MLS® # 12763392

$2,595,000

401 N Wabash Avenue 38a, Chicago

3 Beds 3 Baths 3,437 SqFt Residential MLS® # 12761722

$2,595,000

↓ $200,000

5235 S University Avenue, Chicago

7 Beds 6.5 Baths 7,000 SqFt Residential MLS® # 12575960

New

$2,590,000

1842 N Paulina Street, Chicago

6 Beds 5 Baths 0 SqFt Residential MLS® # 12777967

New Open House

$2,550,000

3822 N Hoyne Avenue, Chicago

6 Beds 5 Baths 5,200 SqFt Residential

Open House

Sat, Oct 10th, 2026 @ 1pm - 3pm

MLS® # 12777329

New

$2,500,000

920 W Monroe Street 1101, Chicago

4 Beds 3.5 Baths 2,257 SqFt Residential MLS® # 12777580

New

$2,500,000

225 N Columbus Drive 8006, Chicago

4 Beds 3 Baths 3,437 SqFt Residential MLS® # 12770329

Open House

$2,500,000

1282 W Washington Boulevard 3b, Chicago

4 Beds 3.5 Baths 3,062 SqFt Residential

Open House

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

MLS® # 12615589

New

$2,495,000

540 W Webster Avenue 511, Chicago

3 Beds 3.5 Baths 2,518 SqFt Residential MLS® # 12764415

New

$2,495,000

3443 N Oakley Avenue, Chicago

4 Beds 5 Baths 0 SqFt Residential MLS® # 12731200

$2,490,000

401 N Wabash Avenue 67e, Chicago

3 Beds 4 Baths 3,102 SqFt Residential MLS® # 12634543

$2,489,000

↓ $10,000

2457 W Byron Street, Chicago

5 Beds 7 Baths 5,000 SqFt Residential MLS® # 12630212

$2,456,434

363 E Wacker Drive 1908, Chicago

3 Beds 2.5 Baths 2,537 SqFt Residential MLS® # 12764744

$2,400,000

230 W Saint Paul Avenue, Chicago

9 Beds 0 Baths 0 SqFt Residential Income MLS® # 12764691

$2,400,000

6022 N Ionia Avenue, Chicago

5 Beds 5.5 Baths 6,000 SqFt Residential MLS® # 12737340

$2,399,999

118 E Erie Street 37h, Chicago

3 Beds 3.5 Baths 3,661 SqFt Residential MLS® # 12723162

New Open House

$2,395,000

616 W Willow Street, Chicago

5 Beds 0 Baths 0 SqFt Residential Income

Open House

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

MLS® # 12779848

Prev

1 2 3 4 5 6 7 8 22

Next

Tags

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