How to get cheaper airfare

What dates are you travelling BWI to Milan?

Tap Portrugal or other lesser known carriers
TAP is a the national flag carrier of Portugal, definitely not a "lesser known" one.

Does anyone know ways to get these flights to count towards mileage points or ways to get other flights for free?
Many mileage programs allow you to accumulate mileage flown on other than the issuing carrier. Check the T&Cs of your mileage program.

I was then planning on flying home from somewhere like Germany, or Prague
Keep in mind that a) two one-way intercontinental tickets will cost you much more than a round-trip ticket with flexible return date (check the fare details before you commit yourself, the cheapest fares don't allow any changes after purchase) and b) many countries list an onward ticket as an entry requirement and not possessing one may result in being denied boarding when you check in at BWI.
Note that the onward ticket does not necessarily have to be to the US, as long as you leave the country (or, in case of Germany and Czech Republic, the Schengen Area).

so I can stay longer If I would like
Should you be planning to stay in Europe longer than 90 days, make sure you don't overstay your 90-per-180 day allowance in the Schengen Area ([http://en.wikipedia.org/wiki/Schengen_Area]).

-I was planning on leaving around mid to late May. Anywhere from the 20th-30th.

1) I guess I meant more in terms of carriers from here. Seems like many people go with the big names like delta or what not

2) Alright I will check into the terms and uses. Didn't know if they could count towards other countries carriers

3) Yes I was going to purchase a one way ticket there. Then as the tickets back get cheaper bit closer to my departure date I was going to order one of them. So I will have a departure ticket on me by the time I leave the country if that is what you mean.

4) Thanks for the call, didn't take that into consideration. The most I should be staying is around 70 so I should be good due to commitments back home. But good idea for me to consider just in case things change.

What date did you find that BWI - Milan student flight for $377?

I found it from new york. Its like 440 from BWI. Around May 28th

That really is a good price. If it was me, I would buy it now!

Alright I will check into the terms and uses. Didn't know if they could count towards other countries carriers

TAP is a member of Star Alliance as well as United and US Airways so if you are a member of the FF program of United or the FF program of US Airways they could count. You'll need to read the terms and conditions of the relevant FF program because not all fares count (and not all the fares that count count the same) though. BTW, if you are a member of a FF program of any airline(s), it's always a good idea to know what airlines allow you to earn miles. Sometimes an airline is only slightly more expensive than other but allows you to earn miles while the cheapest one doesn't allow it...

What are the lesser known carriers flying between the US and Europe? I wouldn't imagine there be many - if any really.

Yes I was going to purchase a one way ticket there. Then as the tickets back get cheaper bit closer to my departure date I was going to order one of them

Here's how it works, airlines have a set amount of seats in a certain class (I'm not talking about Business, Premium and Economy but a fare class where the seats may be the same but the T&Cs may be different). So there may be, say 8 classes of economy seats which get gradually more expensive. As a result the first ones to sell are the cheaper ones and, generally, as you get closer to the date of travel you find that the tickets get gradually more and more expensive unless, by luck, someone who'd bought a cheaper class ticket cancels it and that seat becomes available again. In other words the longer you wait to buy your flight the more expensive it is likely to be. Not the other way around.

Also, though this is happening less than it used to, it is still common for return tickets to end up being cheaper than one-way tickets so worth looking into that.

In the end, quite often the ticket itself is not that expensive but the taxes are very expensive.

Thanks for the info, I will try to book it this week then. Don't think I'll beat $377. Also according to the site i read about the fees/taxes. And that price includes all taxes and everything. So I think I may just book it to be safe, then figure rest out from there.