If the pressure in the transporter room is the same as the pressure where you're beaming to your ears would not pop. I've never seen or heard of anything that states that in a Federation Transporter room the pressure is equalized to the destination. However keep in mind that your ears would pop once the pressure in the transporter room was changed, and whoever is running the transporters at the time would have ear popping pretty regularly each time a transport started, he/she walked out of the room, etc. So they'd pop before being transported.
If it's not pressurized in the transporter room it would be virtually impossible to pressurize the destination location. Are you going to pressurize an entire planet or large enough area that the person wouldn't be affected? The transporter isn't going to displace that much space and it would immediately shift back to the original pressure even if the transporter were capable of such a feat.
The third possibility is the transporter does something to you internally to adjust your ear drums, eustation tubes, etc. That would seem not possible, but transporters don't really make sense anyway, at least in the Star Trek universe, remember it's Science FICTION.
The answer above with the passage about Geordi needs further explanation as to the context. I'm assuming what Geordi is saying is that as a person goes through transport the environmental pressure around them slowly changes so it won't be an abrupt change. The transporter converts matter to energy (pattern+energy stream whatever that means) and then back to matter. I'm not sure exactly how atmospheric pressure would play into that or be converted into energy. Pressure is not a thing you can transport, it's a condition based on certain scientific principles. Either way, the change would be the same for the person whether it takes .02 seconds or 2 seconds. Your body doesn't adjust any different to those small time increments.
I took college level physics, chemistry, organic chemistry, physics, botany, and electronics. I took those classes at a top 20 university at the time, albeit it was a long time ago. So I'm not going to put citations for what are essentially scientific facts.
Hope I didn't confuse things more. :)