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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363 E Wacker Drive 5801, Chicago

$4,350,000

363 E Wacker Drive 5801, Chicago

3 Beds 3 Baths 3,725 SqFt Residential MLS® # 11910436

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199 E Lake Shore Drive 8w, Chicago

$4,300,000

199 E Lake Shore Drive 8w, Chicago

3 Beds 3.5 Baths 4,000 SqFt Residential MLS® # 12623439

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435 N Michigan Avenue 1112, Chicago

$4,300,000

435 N Michigan Avenue 1112, Chicago

4 Beds 3.5 Baths 3,444 SqFt Residential MLS® # 12454488

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New
920 W Monroe Street 504, Chicago

$4,250,000

920 W Monroe Street 504, Chicago

4 Beds 3.5 Baths 3,640 SqFt Residential MLS® # 12777609

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159 E Walton Place 22a, Chicago

$4,250,000

↓ $350,000

159 E Walton Place 22a, Chicago

3 Beds 4 Baths 5,500 SqFt Residential MLS® # 12677656

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1447 N Dearborn Street 3n, Chicago

$4,100,000

1447 N Dearborn Street 3n, Chicago

4 Beds 3.5 Baths 4,273 SqFt Residential MLS® # 12733402

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111 S Peoria Street Ph03, Chicago

$4,000,000

111 S Peoria Street Ph03, Chicago

3 Beds 3.5 Baths 3,701 SqFt Residential MLS® # 12729476

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New
840 N Lake Shore Drive 401-402, Chicago

$3,950,000

840 N Lake Shore Drive 401-402, Chicago

5 Beds 6 Baths 6,355 SqFt Residential MLS® # 12775546

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Open House
224 N Elizabeth Street T1-7c, Chicago

$3,950,000

224 N Elizabeth Street T1-7c, Chicago

3 Beds 3.5 Baths 0 SqFt Residential
Sat, Oct 10th, 2026 @ 10am - 12pm
MLS® # 12672608

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401 N Wabash Avenue 85b, Chicago

$3,900,000

401 N Wabash Avenue 85b, Chicago

4 Beds 4.5 Baths 4,000 SqFt Residential MLS® # 12737363

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30 W Oak Street 7b, Chicago

$3,900,000

30 W Oak Street 7b, Chicago

3 Beds 3.5 Baths 3,349 SqFt Residential MLS® # 12731201

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Open House
224 N Elizabeth Street T1-2a, Chicago

$3,825,000

224 N Elizabeth Street T1-2a, Chicago

4 Beds 4.5 Baths 0 SqFt Residential
Sat, Oct 10th, 2026 @ 10am - 12pm
MLS® # 12672580

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New
1440 N Lake Shore Drive 22abcd, Chicago

$3,800,000

1440 N Lake Shore Drive 22abcd, Chicago

4 Beds 4.5 Baths 4,800 SqFt Residential MLS® # 12739715

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New
363 E Wacker Drive 5401, Chicago

$3,795,000

363 E Wacker Drive 5401, Chicago

3 Beds 3 Baths 3,448 SqFt Residential MLS® # 12778394

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New
2550 N Lakeview Avenue S1506, Chicago

$3,550,000

2550 N Lakeview Avenue S1506, Chicago

3 Beds 3.5 Baths 2,813 SqFt Residential MLS® # 12765672

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New
435 N Michigan Avenue 1105, Chicago

$3,525,000

435 N Michigan Avenue 1105, Chicago

4 Beds 4.5 Baths 3,950 SqFt Residential MLS® # 12751549

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New
920 W Monroe Street 1102, Chicago

$3,500,000

920 W Monroe Street 1102, Chicago

4 Beds 3.5 Baths 3,136 SqFt Residential MLS® # 12777596

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New
1447 N Dearborn Street 1s, Chicago

$3,500,000

1447 N Dearborn Street 1s, Chicago

4 Beds 4.5 Baths 3,725 SqFt Residential MLS® # 12733393

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270 E Pearson Street 701-801, Chicago

$3,500,000

270 E Pearson Street 701-801, Chicago

5 Beds 6.5 Baths 6,860 SqFt Residential MLS® # 12658546

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401 N Wabash Avenue 44a, Chicago

$3,500,000

401 N Wabash Avenue 44a, Chicago

3 Beds 4.5 Baths 3,948 SqFt Residential MLS® # 12640133

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Open House
435 N Michigan Avenue 1703, Chicago

$3,400,000

435 N Michigan Avenue 1703, Chicago

3 Beds 3.5 Baths 3,390 SqFt Residential MLS® # 12053386

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401 N Wabash Avenue 48a, Chicago

$3,300,000

401 N Wabash Avenue 48a, Chicago

3 Beds 4.5 Baths 3,948 SqFt Residential MLS® # 12745466

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New
14 N Peoria Street 6h-7h, Chicago

$3,299,000

14 N Peoria Street 6h-7h, Chicago

4 Beds 4 Baths 5,100 SqFt Residential MLS® # 12679827

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New
800 N Michigan Avenue 4801, Chicago

$3,250,000

800 N Michigan Avenue 4801, Chicago

3 Beds 2.5 Baths 4,200 SqFt Residential MLS® # 12634613

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Posted by Leo Clark. on

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