To be honest, I´m probably not the person to answer this question, but I´ve done the trip a few times, so I have some idea.
Best deal that´s ever happened, as far as I know, is $530 through Turkish Airlines, direct flight from NY or DC to IST, and back. Normally, this is probably going to be $800–$1500. If you´re not in NY or DC, you´re probably going to have to get yourself on a Delta or United ticket operated, after at least one layover, by Turkish or Lufthansa.
In my experience, the cheapest flights on a normal day (no special deals) are two-stop flights through 1) New York and 2) Hamburg/Frankfurt/Munich to Istanbul. Expect to pay $900-$1200.
If you had money to burn, though, I´d say go Turkish Airlines—they´re easily the most comfortable, and they offer more direct flights. In fact, I´d pay an extra $200 to fly Turkish after doing the United/Delta Germany layovers. Not pleasant.
As for other tips—not much more I can say than a good guidebook could. June will be busy, so prioritize the touristy stuff you want to see: There will be lines. Otherwise, have fun.
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