If you all are on the same reservation under the same confirmation number, you only need to enter the confirmation number and one passenger name to pull up all of the passengers for check in. Once at that window, you will check the box next to each passenger name and the check everyone in with one click. If you are under multiple reservations with multiple confirmation numbers you will need to enter each confirmation number and passenger name separately. You can open multiple browser windows and get information plugged into each to speed the process in the latter situation.
You can bring a cooler with a lunch in it as long as you don't have any liquids or gels in it. So no drinks, yogurts, puddings, etc. Also, mayo, mustard, etc. are OK if they are spread on a sandwich but would have to be in your 3-1-1 bag if they are in packets. Ice packs are not allowed either (except to keep medicines cold), but you can freeze a bag of grapes and put that in the cooler to help keep the food cold.