Honestly? I’d probably leave around 1pm. Maybe earlier. To be safe you need to get to Logan by 6:30 (only to find out your flight is delayed, I’m sure) because they’ll have super long security lines tonight. Two hours early is kind of a minimum at the holidays. The problem is that it means you need to hit Boston right at rush hour on TOP of holiday traffic making this one of the worst driving days of the year. If you leave at 1, you’ll hopefully get there before rush hour, if you get caught up in AWFUL traffic it is okay, and you know—bring a book or whatever and read at the terminal. Getting to the airport early isn’t the end of the world. Getting there late is a problem. Leave: 1pmish. Allow: 1 hour in a traffic jam. Arrive: 5:30ish. Stand in line to check in: 6pm Stand in line for security: Who knows? Hopefully less than an hour. Arrive at gate at least an hour early. Get out packed dinner and eat. Read book. Do the crossword. Do sudoku. Wish you didn’t get there so danged early. Wonder when you started acting like your mum about airports. Sigh. Board flight. This advice comes from my mom’s book of airport advice. She’s definitely of the “it doesn’t matter if you are three hours early, better than 1 minute late” variety.