Chester sits next to 4 phonetic neighbors — Lester, Jester, and Webster are the closest matches by sound. Most share Chester's English-origin cluster, so the rhythm and vowel shape carry across the list.
You searched for names like
"fortress, walled Roman camp"
"elf friend, noble friend"
"gracious defender"
"son of Jack"
"spear"
"little bear, bear cub"
"power of peace"
"modern American invented name"
"falling, resolution"
"son of the prosperous protector"
"follower of Calvin (in Protestant tradition)"
"place of elms"
"the Nubian, dark-skinned"
"red-haired, little redhead"
"peaceful ruler"
"from the pool or marsh"
"son of Rand, son of the shield-wolf"
"fair, attractive"
"modern invented name"
"steps over a fence or wall"
"of the sea (possible etymology)"
Similar sound: These names share phonetic patterns with Chester — similar vowel sounds, consonant clusters, or rhythm.
Shared roots: Several names on this list have Latin origins, giving them the same cultural heritage as Chester.
Rhythm: Chester is a 2-syllable name. Names with the same syllable count tend to feel interchangeable when you're narrowing your list.