The Devil is in the details. Is that a Chicago drill press, or a Chicago Electric drill press? Harbor Freight sell some Chicago Electric tools, but no drill press, likely sold yours, which I do not know if the name was changed to Central Machinery (they carry Central Machinery drill presses). You can always download a free owner's manual from HF. Get a universal drill chuck key for $4-5 and set for any tool. Or, you can look on-line for an owner's manual, but you have to join to get one, and I won't join, so don't know how that works. Or, you can go to ebay, and see what you can find.
If it were me, I'd just go to HF, download a free drill press manual (how different can they be?), and buy a universal chuck key.
Woodworking doesn't need to break the bank. I likely have just around $1300 spent on shop, and tools, maybe a tad more, but I'll bet under $1500. Buy used tools, I've got 3 routers that were given to me, they all work, newest router of 5 is around 20 years old. Shop is 8X12, bought in about 1996, when I had the money to spare. Army, retired 1981.
