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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159 E Walton Place 8d, Chicago

$1,850,000

159 E Walton Place 8d, Chicago

3 Beds 3.5 Baths 3,157 SqFt Residential MLS® # 12719761

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New
2026 N Orleans Street 1s, Chicago

$1,849,000

2026 N Orleans Street 1s, Chicago

4 Beds 3.5 Baths 0 SqFt Residential MLS® # 12771434

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229 E Lake Shore Drive 10e, Chicago

$1,824,999

↓ $24,001

229 E Lake Shore Drive 10e, Chicago

4 Beds 4 Baths 3,735 SqFt Residential MLS® # 12566727

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New
111 E Chestnut Street 56ab, Chicago

$1,800,000

111 E Chestnut Street 56ab, Chicago

2 Beds 2.5 Baths 2,600 SqFt Residential MLS® # 12754110

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111 S Peoria Street 313, Chicago

$1,800,000

111 S Peoria Street 313, Chicago

4 Beds 4.5 Baths 0 SqFt Residential MLS® # 12743577

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175 E Delaware Place 7201-7202, Chicago

$1,800,000

175 E Delaware Place 7201-7202, Chicago

3 Beds 3 Baths 3,050 SqFt Residential MLS® # 12697463

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New Open House
339 W Webster Avenue 1a, Chicago

$1,799,000

339 W Webster Avenue 1a, Chicago

4 Beds 3.5 Baths 0 SqFt Residential
Sat, Oct 10th, 2026 @ 11am - 12:30pm
MLS® # 12781486

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New
180 E Pearson Street 3807, Chicago

$1,797,000

180 E Pearson Street 3807, Chicago

3 Beds 3 Baths 2,754 SqFt Residential MLS® # 12781063

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435 N Michigan Avenue 408, Chicago

$1,795,000

↓ $80,000

435 N Michigan Avenue 408, Chicago

2 Beds 2.5 Baths 1,949 SqFt Residential MLS® # 12750924

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450 E Waterside Drive 3409, Chicago

$1,789,000

↓ $40,000

450 E Waterside Drive 3409, Chicago

2 Beds 3 Baths 2,714 SqFt Residential MLS® # 12690367

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1040 N Lake Shore Drive 7c, Chicago

$1,775,000

1040 N Lake Shore Drive 7c, Chicago

3 Beds 3.5 Baths 3,050 SqFt Residential MLS® # 12674926

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800 N Michigan Avenue 3301, Chicago

$1,775,000

800 N Michigan Avenue 3301, Chicago

2 Beds 2.5 Baths 2,300 SqFt Residential MLS® # 12654190

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New
920 W Monroe Street 502, Chicago

$1,750,000

920 W Monroe Street 502, Chicago

3 Beds 2.5 Baths 1,669 SqFt Residential MLS® # 12777524

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161 E Chicago Avenue 44a, Chicago

$1,750,000

161 E Chicago Avenue 44a, Chicago

3 Beds 2.5 Baths 0 SqFt Residential MLS® # 12751115

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New Open House
2235 W Oakdale Avenue 16-b, Chicago

$1,750,000

2235 W Oakdale Avenue 16-b, Chicago

5 Beds 4.5 Baths 3,885 SqFt Residential
Sun, Oct 11th, 2026 @ 1pm - 3pm
MLS® # 12735373

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159 E Walton Place 5c, Chicago

$1,750,000

159 E Walton Place 5c, Chicago

3 Beds 3.5 Baths 3,672 SqFt Residential MLS® # 12705829

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2468 N Orchard Street M-s, Chicago

$1,750,000

2468 N Orchard Street M-s, Chicago

3 Beds 2.5 Baths 2,644 SqFt Residential MLS® # 12650366

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New Open House
1951 W Dickens Avenue 3, Chicago

$1,725,000

1951 W Dickens Avenue 3, Chicago

3 Beds 2.5 Baths 0 SqFt Residential
Sat, Oct 10th, 2026 @ 11am - 12:30pm
MLS® # 12761626

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Open House
2235 W Oakdale Avenue 18-b, Chicago

$1,725,000

2235 W Oakdale Avenue 18-b, Chicago

4 Beds 3.5 Baths 3,885 SqFt Residential
Sun, Oct 11th, 2026 @ 1pm - 3pm
MLS® # 12718571

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3617 N Magnolia Avenue 1, Chicago

$1,725,000

3617 N Magnolia Avenue 1, Chicago

4 Beds 4.5 Baths 0 SqFt Residential MLS® # 12565261

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363 E Wacker Drive 4803, Chicago

$1,717,000

363 E Wacker Drive 4803, Chicago

2 Beds 2 Baths 1,629 SqFt Residential MLS® # 12748130

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New
159 E Walton Place 7d, Chicago

$1,700,000

159 E Walton Place 7d, Chicago

3 Beds 3.5 Baths 3,157 SqFt Residential MLS® # 12781373

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1923 N Damen Avenue Ph, Chicago

$1,700,000

1923 N Damen Avenue Ph, Chicago

4 Beds 3.5 Baths 3,400 SqFt Residential MLS® # 12748419

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401 N Wabash Avenue 49i, Chicago

$1,700,000

401 N Wabash Avenue 49i, Chicago

2 Beds 2.5 Baths 2,200 SqFt Residential MLS® # 12455297

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Posted by Leo Clark. on

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