These two bags get mixed up in feeds because both are quilted and both have a chain. They are not the same purchase.
Classic Flap
Look for “classic”, “double flap” or “2.55” and a turn-lock. The chain is usually interwoven with leather. It is the softer, older shape. Medium is the reference size.
Boy
The Boy bag title usually says Boy. The hardware is a rectangular clasp with sharp edges, not the Classic turn-lock. The bag is more structured. Old-medium and new-medium are different fits. If the title does not say Boy, do not treat a rectangular clasp photo as a guess: go back to the words.
How to compare a price
Compare Boy with Boy, and medium Classic with medium Classic, in the same leather. A Boy in caviar is not a deal just because it costs less than a jumbo Classic in lambskin. Both are in the catalog below when the partner has them.
Boy listings

Chanel Navy Blue Quilted Caviar Leather Medium Boy Bag
Original price was: $5,548.$5,048Current price is: $5,048.
Buy now
Chanel Red Old Medium Lambskin and Fur Boy Flap
$3,641
Buy now
Chanel Cream Old Medium Chevron Lambskin Boy Flap
$4,500
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Chanel Navy Blue Small Chevron Aged Calfskin Jacket Boy Flap
$4,289
Buy now
Classic Flap listings

Chanel Black Chevron Caviar Leather Medium Classic Double Flap Bag
Original price was: $9,319.$8,819Current price is: $8,819.
Buy now
Chanel Dark Red Quilted Caviar Leather Maxi Classic Single Flap Bag
Original price was: $7,375.$6,875Current price is: $6,875.
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Chanel Off White Quilted Satin Vintage Flap Bag
$1,435
Buy now
Chanel Red Chevron Patent Leather New Mini Classic Flap Bag
Original price was: $6,621.$6,121Current price is: $6,121.
Buy now
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