One HD antenna, two tvs

On thing not mentioned yet is that all TV's need to have their individual "Auto scans" run to put the channels found into their memories. Since not all televisions are created equal you may find that each TV might not find all the same channels with the antenna aimed in a given direction.

The job may be easier/harder than you think (Easier cause you need spend less money, harder due to cable routing).

First: If you are talking over the air,, There is no such thing as an HD Antenna, it is an antenna period,, DirecTV has HD antennas, Dishnetwork,, the 1000 antennas are HD, but OTA you just say ANTENNA.

Now to the issue:

if your "Booster" (which by the way it is not) is a wall plate, then on the back there should be a 3rd port which is named TV-2 (will likely not be labeled) the 3 ports, left to right, with the 12 volt accessory socket at the top, and looking at the back are

Rooftop antenna = Park Cable = TV-2 (And if there is a 4th TV-3)

As the other person said, so long as both stations are on the same heading (no need to rotate the antenna) will work very well.. I know.. I do it that way

Recommendations:
1: Use quality RG-6, not RG-59,, often the cost is the same in 100 foot or less rolls but the signal delivered may be much better with RG-6.

2: you night consider changing that wall plate to a SENSAR PRO if your antenna is a winegard Many many advantages

we do it all the time. one in the living area and one in the bed room.

YES.. as long as the antenna does not have to be rotated

the 2nd TV should get all the stations the front TV can receive

it will not get one coming from a different direction

can't watch Chicago & Indianapolis at the same time

Sure , as long as the channels are in the same initial scan range .