With the busy fall season approaching, we thought we’d take a closer look at where some of Chicago’s most expensive condos currently on the market are listed, and what each of these lavish and luxurious units have to offer. Not surprisingly, No. 9 Walton, Waldorf Astoria Chicago, and Trump Tower feature the three highest priced condos right now, each boasting a price tag of well over $12 million. Somewhat unexpected, just two condos over at Vista Tower are among some of the Windy City’s 25 most expensive units on the market right now, which is the same number of units you’ll see listed over at The Palmolive in that same category.

The spectacular new One Bennett Park condo tower also features a couple condos in the $6 million price range, and you’ll also see the sprawling 6,597 square foot penthouse over at the Ritz Carlton Residences still on the open market as well, which is asking $9,500,000.

And while we’re talking penthouses, #PH1 over at 900 West Washington is also still available for $5,679,999, and the penthouse over at the chic new 61 West Erie development, which has four bedrooms, four bathrooms, and 5,800 square feet of living space is also on the market with an asking price of $5,850,000.

Browse Chicago's Most Expensive Condos Currently on the Market:

Check Out Chicago's Most Expensive Condos For Sale Below:, Over $1,000,000

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435 N Michigan Avenue 812, Chicago

$1,575,000

435 N Michigan Avenue 812, Chicago

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

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401 N Wabash Avenue 81f, Chicago

$1,575,000

401 N Wabash Avenue 81f, Chicago

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

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New
600 N Lake Shore Drive 3011, Chicago

$1,550,000

600 N Lake Shore Drive 3011, Chicago

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

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New
600 N Lake Shore Drive 1305, Chicago

$1,550,000

600 N Lake Shore Drive 1305, Chicago

3 Beds 3.5 Baths 0 SqFt Residential MLS® # 12688483

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Open House
224 N Elizabeth Street T2-3b, Chicago

$1,550,000

224 N Elizabeth Street T2-3b, Chicago

2 Beds 2.5 Baths 0 SqFt Residential
Sat, Oct 10th, 2026 @ 10am - 12pm
MLS® # 12672114

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850 N Lake Shore Drive 405, Chicago

$1,550,000

↓ $65,000

850 N Lake Shore Drive 405, Chicago

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

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Open House
363 E Wacker Drive 5105, Chicago

$1,549,000

↓ $50,000

363 E Wacker Drive 5105, Chicago

2 Beds 2 Baths 0 SqFt Residential
Sun, Oct 11th, 2026 @ 12pm - 2pm
MLS® # 12622718

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161 E Chicago Avenue 49a, Chicago

$1,525,000

161 E Chicago Avenue 49a, Chicago

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

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New
1160 S Michigan Avenue 4101, Chicago

$1,525,000

1160 S Michigan Avenue 4101, Chicago

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

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55 E Erie Street 4503, Chicago

$1,500,000

55 E Erie Street 4503, Chicago

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

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New
2640 N Bosworth Avenue Phs, Chicago

$1,499,900

2640 N Bosworth Avenue Phs, Chicago

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

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New
950 N Michigan Avenue 3103, Chicago

$1,499,900

950 N Michigan Avenue 3103, Chicago

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

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New
600 N Lake Shore Drive 4211, Chicago

$1,499,000

600 N Lake Shore Drive 4211, Chicago

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

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3726 N Ashland Avenue Ph, Chicago

$1,499,000

3726 N Ashland Avenue Ph, Chicago

4 Beds 3.5 Baths 0 SqFt Residential MLS® # 12752459

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910 W Madison Street 904e, Chicago

$1,499,000

910 W Madison Street 904e, Chicago

3 Beds 3 Baths 2,500 SqFt Residential MLS® # 12745354

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505 N Lake Shore Drive 4901-12, Chicago

$1,499,000

505 N Lake Shore Drive 4901-12, Chicago

3 Beds 3.5 Baths 3,000 SqFt Residential MLS® # 12737459

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Open House
3700 N Lake Shore Drive 104, Chicago

$1,495,000

3700 N Lake Shore Drive 104, Chicago

4 Beds 3 Baths 3,001 SqFt Residential
Sat, Oct 10th, 2026 @ 11am - 1pm
MLS® # 12769204

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New
1319 N Sandburg Terrace, Chicago

$1,495,000

1319 N Sandburg Terrace, Chicago

4 Beds 4 Baths 2,850 SqFt Residential MLS® # 12762102

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401 N Wabash Avenue 74f, Chicago

$1,495,000

↓ $105,000

401 N Wabash Avenue 74f, Chicago

2 Beds 2.5 Baths 1,952 SqFt Residential MLS® # 12618985

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10 E Ontario Street 5001-02, Chicago

$1,475,000

10 E Ontario Street 5001-02, Chicago

3 Beds 3 Baths 2,400 SqFt Residential MLS® # 12754794

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2040 N Damen Avenue 2, Chicago

$1,475,000

2040 N Damen Avenue 2, Chicago

3 Beds 2.5 Baths 2,900 SqFt Residential MLS® # 12743406

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1260 N Astor Street 7, Chicago

$1,475,000

1260 N Astor Street 7, Chicago

5 Beds 5 Baths 4,500 SqFt Residential MLS® # 12743102

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3739 N Clifton Avenue 1, Chicago

$1,465,000

↓ $35,000

3739 N Clifton Avenue 1, Chicago

4 Beds 3.5 Baths 0 SqFt Residential MLS® # 12703271

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1346 W Addison Street 3e, Chicago

$1,450,000

1346 W Addison Street 3e, Chicago

3 Beds 3.5 Baths 2,800 SqFt Residential MLS® # 12772580

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Posted by Leo Clark. on

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