Don't join the Army to fly commercially, the Navy or Air Force is what you want. Also, don't enlist. Enlistedmen now rarely get to the cockpit, are treated as "second class" servicemen and don't have as many benefits as officers.
Basically, find a school with AFROTC or NROTC that you want to go to. There are hundreds of normal colleges with these programs. You'll go to college like normal and all and take an additional course AFROTC or NROTC. These programs, if you apply for them end of junior/beginning of senior year in many cases will pay for most if not all of your college tuition. They will also give you a monthly stipend (pocket money) as well as supply you with uniforms and books.
Then, after you graduate college, if you're entering the Air Force's or Navy's pilot program, you will be sent to pilot school. I'll use the Air Force's program since I'm most familiar with it. At pilot school you will learn how to fly, from the basic single engine eventually up to larger aircraft (either fighters or transports). Once finished with pilot school, you will put in for which base you want to operate out of (this will have to accord with the type of aircraft you fly). You'll then relocate there (or if they can't accomodate you with that, to a second or third choice) join a flight squadron usually and be on your first "tour". You'll also be a first lieutenent, meaning your pay will be more than most enlistedmen, and you could even be in charge of a group or enlistedmen. You're then required to finish up your 10 years of service, most days just flying practice missions. Now, in times of war, there is a good chance you and your squadron will be assigned to wherever the closest Allied Air Force Base is to help with support or strike etc... One benefit about the Air Force, compared to the Navy and Army is that in the Air Force, many times, you will operate out of the US or England etc.. (nicer places than the sea or sand). Once you're commitment is up, then you're free to go, and will almost be guaranteed a job.
Now, if you're really into the military and want to attend some of the best colleges in the world, then I would suggest looking into the Service Academies, the three main and best ones being the United States Naval Academy, United States Air Force Academy and the United States Military Academy. These are military institutions, and admission is highly competitive (last year the USAFA's admission rate was like 10% as was USNA
and Army). But if you have good grades (around a 3.0), good SAT
's (around 1300 SAT
) and are involved in your school (i.e. captain of a team, president of a club, national honor society, president of your class etc...) you have a good shot. You'll need a nomination from your senator or congressman/woman also to attend. (i.e. all you'll do is send a letter to them stating that you want to attend an academy, and they'll set up an interview and then if they determine you qualified will give you a nomination).
Basically, these are military colleges. They are free, and very disciplined. You'll leave your home late June to go to BCT (Basic Cadet Training), which entails a month and a half of tough military training. After that (and something called recognition), the academies somewhat turn into regular colleges. You go to class normally etc... but in uniform, and adhere to strict rules which ease as you get older.
Anyway, check out:
http://www.usafa.af.mil For the United States Air Force Academy. You'll find out about everything you want about admissions, cadet life etc... on there
For the navy it's: http://www.usna.edu
If ROTC seems like more of what you want then check out:
http://www.afrotc.com for Air Force and http://www.nrotc.com for Navy.
You'll find out a lot more about the programs there.
To answer your question. If you join a service (which with your grades and all, you don't want to enlist, rather apply for an AFROTC or NROTC scholarship or an academy), you'll be sent out for basic training, which depending on which branch of service you join is at different places. Basic is an introduction to military life and how to work as a team etc... but is tough. Then you'll be sent to a military base and will follow officers' orders. Most of the people dying on the front lines are enlistedmen, not officers.. btw. So if you do ROTC or go to an academy, sure you will most likely be in danger, but are not always on the front lines or doing the man to man combat. Also, I don't know if you were using Chicago as an example, but if you plan on living there all the while becoming a pilot the civilian route, then you're in for an awakening. Basically going the civilian route, you're going to have to leave Chicago anyway for various reasons.
Anyway, check out the above links, and if you think it's something for you then look into them further, you still have at least a year!