list_to_search = ["Birding", "Large Bird Handling"] search_key = "Bird" # first list comprehension will match *any* location # case-sensitive result_any_position_case_sensitive = [item for item in list_to_search if search_key in item] # case-insensitive result_any_position = [item for item in list_to_search if search_key.lower() in item.lower()] # second list comprehension will match only at the beginning of each word # regex is the better solution for this # case sensitive result_beginning_of_word_case_sensitive = [item for item in list_to_search if item.startswith(search_key)] # case insensitive result_beginning_of_word = [item for item in list_to_search if item.lower().startswith(search_key.lower())]