I've always taken my medications (all pills except for maintenance/rescue inhalers) in my carry-on with no issues. I do put them in a daily pill holder (plus pack a few extra). I've never had any issues. Basically, the items I pack in my carry-on are those I would not want to lose - laptop, medications, chargers/plugs for electronics (I place each one in a separate zip-top bag), itinerary information (airline, hotel confirmation, Magical Express vouchers, etc.), a change of clothes and/or bathing suit. My cell phone and iPod I usually carry in my handbag. In checked luggage is mainly clothes, shoes, toiletries, a paperback/magazine. We have a scale to weigh our luggage before we leave for the airport - I don't want any surprises! .