With a $200 budget you are definitely shopping on Craigslist for used bikes, or back at Wal-Mart & Target. Bicycle shops and the Big 4 companies (Cannondale, Trek, Giant, Specialized) don't try to compete with Wal-Mart. They make better bikes that generally start around $500. Let's assume 50% discount on CL... even starting with a really cheap Trek, $200 may not be feasible for a bike in decent working order. (I would not buy a rundown, neglected bike.)
You should look for a multispeed hybrid or city bike. They will fit your needs. A rear rack will be better than any front-mounted basket because it won't affect your steering and generally they hold a lot more weight.
Regarding theft, ALWAYS lock it. Get a quality cable at least 1/2" or 12mm thick, not a thin & cheap one that can easily be cut. A thick cable can be cut too, but it takes huge tools that may/would draw attention. I personally disfavor U-Locks because yes they are really tough but you can't lock both wheels and the frame without a cable.