engagement ?

So my boyfriend and I just recently celebrated our one year  (January 14th). Him and myself have talked plenty of times of getting married and having kids. And with him and I loving to phili in July. We have talked about getting engaged Here since this is where my family all is and in a year or two we would come back home to have our wedding ... him and I are soon taking a trip to Chicago with his friend and girlfriend. For the Valentine's Day weekend.  Should I be cautious about him popping the question?