Traveling tips?

kris
We're looking at taking a thanksgiving trip when little guy turns 3 months old. We want to travel from Indiana to family in Dallas. We honestly have no idea if it's better to fly or drive. It's a long trip, we're considering driving just because there's so much stuff with a baby and room would be an issue if we flew. I also have to pump every couple of hours to feed little guy so flying would be tough cause where do you pump? Feeding him directly from the breast just hasn't worked out. Maybe he'll latch better by November. Then I wouldn't care if he nursed in the airport. I just feel weird pumping there in public. 
If we fly, what do we pack for baby to sleep in? Our family doesn't have a crib or any place for him to sleep. 
So experienced mommas, what are the pros and cons with flying or driving across country?