With the exception of certain grasshoppers, insects are not kosher. In fact, before Jews eat lettuce or other produce known to be infested with bugs, they check it carefully to be sure that it is bug free.
That said, even though insects are not kosher for consumption, Judaism has some complimentary things to say about creepy crawlies. The sages tell us how King David wondered why G‑d created spiders and mosquitoes. G‑d arranged things so that David was once hiding from King Saul in a cave. A spider came and spun a web over the opening of the cave, making it seem that no one had entered in a long time, thus saving David from discovery. At another point, a well-placed mosquito bite to Saul’s general, Abner, allowed David to run to safety.
According to the United States Federal Department of Agriculture, certain amounts of insects are permitted in foods.
Would one still be considered as following the rules of kosher if eating food which is likely to have insects in it? Wouldn't it have to be as otherwise people couldn't really eat it?
Food items that are likely to have insects are indeed problematic from a kosher perspective. That's why certain fruits and vegetables which have a history of infestation that is considered acceptable by the USDA still need to undergo an additional rigorous washing for them to be kosher.