Classic Mercedes-Benz for sale in Chicago, IL
Classic Mercedes-Benz cars listed for sale in Chicago, Illinois, each with photos, the asking price and a link to the seller. 4 cars are listed here; 3 for sale and 1 marked sold; asking prices from $17,500 to $159,800; located in Illinois.
Photos coming soon
$17,500 · 43% below typical147,000 miles · Automatic · Silver
Chicago, IL
SOURCE: eBay
$17,500
43% below the typical asking price for a 560SL
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Seller: sampor22
Transmission: Automatic
Condition: I love this car. 147,000 miles Never thought I would part with it everywhere I used to go. People would take pictures. This car is in concourse condition.
Color: Silver (180)
$18,800 · 8% above typicalMileage not stated on Hemmings
Chicago, IL
SOURCE: Hemmings
$18,800
8% above the typical asking price for a 380SL
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Condition: No condition description was captured from this Hemmings listing at harvest (Nov 2, 2026) — the Hemmings page and the seller are the source of truth for condition, history, and specification.
Photos coming soon
$159,800 · 27% above typicalMileage not stated
Chicago, IL
SOURCE: Hemmings
$159,800
27% above the typical asking price for a 280SE
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Seller: Dealer
Condition: Hemmings listing in Chicago, IL — the harvest captured no condition description for this car; the seller's full description is on the Hemmings page.
8,000 miles · Four-Speed Automatic · Light Blue
Chicago, IL
SOURCE: Bring a Trailer
$240,000
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Seller: Auction seller
Transmission: Four-Speed Automatic
Condition: Listing details from the car's own Bring a Trailer page: Chassis: 11102712001320; 8k Miles Shown on Rolled Odometer; 3.5-Liter V8; Four-Speed Automatic Transmission; Repainted Light Blue; Blue Leather Upholstery; Blue Soft Top; 14” Steel Wheels w/Covers; Becker AM/FM Radio; Air Conditioning.
Color: Light Blue (334)