In[]:=
txt={"Los Angeles REPORT November 30, 2019 - December 31, 2020","Chicago REPORT February 01, 2023 - February 28, 2023"}
Out[]=
{Los Angeles REPORT November 30, 2019 - December 31, 2020,Chicago REPORT February 01, 2023 - February 28, 2023}
In[]:=
yearString=___~~"REPORT"~~___~~","~~Whitespace..->""
Out[]=
___~~REPORT~~___~~,~~Whitespace..
In[]:=
StringReplace[txt,yearString]
Out[]=
{2020,2023}