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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New
600 N Lake Shore Drive 1011, Chicago

$1,450,000

600 N Lake Shore Drive 1011, Chicago

3 Beds 3 Baths 2,124 SqFt Residential MLS® # 12770732

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Open House
3921 N Greenview Avenue 1, Chicago

$1,450,000

3921 N Greenview Avenue 1, Chicago

5 Beds 3 Baths 3,409 SqFt Residential
Sun, Oct 11th, 2026 @ 1pm - 2:30pm
MLS® # 12767401

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New
1839 N Dayton Street 204, Chicago

$1,450,000

1839 N Dayton Street 204, Chicago

3 Beds 2 Baths 0 SqFt Residential MLS® # 12766833

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New
3721 N Kenmore Avenue 1, Chicago

$1,450,000

3721 N Kenmore Avenue 1, Chicago

3 Beds 3.5 Baths 0 SqFt Residential MLS® # 12764345

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2908 N Burling Street 1, Chicago

$1,450,000

2908 N Burling Street 1, Chicago

4 Beds 2.5 Baths 3,400 SqFt Residential MLS® # 12755796

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914 W Fletcher Street 1, Chicago

$1,450,000

914 W Fletcher Street 1, Chicago

4 Beds 3.5 Baths 0 SqFt Residential MLS® # 12681838

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New
1919 S Prairie Avenue 3, Chicago

$1,449,000

1919 S Prairie Avenue 3, Chicago

3 Beds 2.5 Baths 3,700 SqFt Residential MLS® # 12766311

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New
600 N Lake Shore Drive 2411, Chicago

$1,449,000

600 N Lake Shore Drive 2411, Chicago

3 Beds 3 Baths 2,124 SqFt Residential MLS® # 12763928

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New
920 W Monroe Street 501, Chicago

$1,425,000

920 W Monroe Street 501, Chicago

2 Beds 2 Baths 1,428 SqFt Residential MLS® # 12777258

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New
1418 N Lake Shore Drive 28, Chicago

$1,400,000

1418 N Lake Shore Drive 28, Chicago

2 Beds 2.5 Baths 3,100 SqFt Residential MLS® # 12760630

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420 W Grand Avenue 5d, Chicago

$1,400,000

420 W Grand Avenue 5d, Chicago

2 Beds 2 Baths 2,500 SqFt Residential MLS® # 12700146

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New Open House
2541 N Wayne Avenue 1n, Chicago

$1,399,900

2541 N Wayne Avenue 1n, Chicago

4 Beds 3.5 Baths 0 SqFt Residential
Sat, Oct 10th, 2026 @ 10am - 12pm
MLS® # 12778351

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New Open House
1951 W Dickens Avenue 1, Chicago

$1,399,000

1951 W Dickens Avenue 1, Chicago

3 Beds 2.5 Baths 0 SqFt Residential
Sat, Oct 10th, 2026 @ 11am - 12:30pm
MLS® # 12761588

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New
2659 N Greenview Avenue, Chicago

$1,395,000

2659 N Greenview Avenue, Chicago

3 Beds 2.5 Baths 3,200 SqFt Residential MLS® # 12770803

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2743 N Greenview Avenue 1, Chicago

$1,395,000

2743 N Greenview Avenue 1, Chicago

3 Beds 2.5 Baths 0 SqFt Residential MLS® # 12767404

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New
2314 N Lincoln Park West 11s, Chicago

$1,395,000

2314 N Lincoln Park West 11s, Chicago

3 Beds 3 Baths 0 SqFt Residential MLS® # 12758736

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57 E Delaware Place 3804, Chicago

$1,395,000

↓ $100,000

57 E Delaware Place 3804, Chicago

2 Beds 2.5 Baths 3,050 SqFt Residential MLS® # 12639998

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310 S Michigan Avenue 1500, Chicago

$1,395,000

↓ $100,000

310 S Michigan Avenue 1500, Chicago

5 Beds 5 Baths 3,400 SqFt Residential MLS® # 12544545

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401 N Wabash Avenue 37k, Chicago

$1,390,000

↓ $110,000

401 N Wabash Avenue 37k, Chicago

2 Beds 2.5 Baths 2,063 SqFt Residential MLS® # 12594795

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New
211 N Harbor Drive 2808, Chicago

$1,385,000

211 N Harbor Drive 2808, Chicago

3 Beds 2.5 Baths 1,574 SqFt Residential MLS® # 12737705

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600 N Lake Shore Drive 2011, Chicago

$1,380,000

600 N Lake Shore Drive 2011, Chicago

3 Beds 3 Baths 2,124 SqFt Residential MLS® # 12765205

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2042 N Racine Avenue 101, Chicago

$1,380,000

↓ $39,000

2042 N Racine Avenue 101, Chicago

4 Beds 2.5 Baths 2,322 SqFt Residential MLS® # 12738892

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New
2745 N Greenview Avenue 1, Chicago

$1,375,000

2745 N Greenview Avenue 1, Chicago

4 Beds 3.5 Baths 2,750 SqFt Residential MLS® # 12777459

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New
900 W Washington Boulevard 504, Chicago

$1,375,000

900 W Washington Boulevard 504, Chicago

2 Beds 2.5 Baths 1,605 SqFt Residential MLS® # 12777400

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Posted by Leo Clark. on

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