...I can only think of two apiece for New York, Los Angeles, Chicago, Detroit and Cleveland:
NEW YORK: WJZ-TV/7 (1948-1953), WOR-TV/9 (1949-1983)
LOS ANGELES: KFI-TV/9 (1949-1951), KHJ-TV (1951-1989)
CHICAGO: WLS-TV/7 (since 1968), WGN-TV/9 (since 1948)
DETROIT: WWJ-TV/4 (1947-1978), WWJ-TV/62 (since 1995)
CLEVELAND: KYW-TV/3 (1956-1965), WJW-TV/8 (1956-1977 and since 1985)
...have I overlooked any other cities of license? Have any had three?...
NEW YORK: WJZ-TV/7 (1948-1953), WOR-TV/9 (1949-1983)
LOS ANGELES: KFI-TV/9 (1949-1951), KHJ-TV (1951-1989)
CHICAGO: WLS-TV/7 (since 1968), WGN-TV/9 (since 1948)
DETROIT: WWJ-TV/4 (1947-1978), WWJ-TV/62 (since 1995)
CLEVELAND: KYW-TV/3 (1956-1965), WJW-TV/8 (1956-1977 and since 1985)
...have I overlooked any other cities of license? Have any had three?...