Well, since Dramamine (regular Dramamine, that is) *contains* Benadryl, you'll likely overdose yourself if you do that.
Actually, Draminine is Benadryl (diphenhydramine) plus theophylline, which changes the chemical from diphenhydramine to dimenhydrinate. Both Benadryl and Dramamine are antihistamines.
Claritin is also an antihistamine, which is way too much antihistamine. What you want to prevent ear pain is a decongestant, and perhaps a mucolytic if you're really stuffy. Talk to your pharmacist; you're most likely to get a recommendation for Mucinex-D or a similar generic. It is worth it to get pseudoephedrine products from behind the counter -- as a decongestant, phenylephrine doesn't work nearly as well for most people.
Non-drowsy Dramamine is actually meclizine, which just keeps you from throwing up. You can take that with Benadryl, but there would be no reason to, because Benadryl will also prevent motion sickness.