First of all, congratulations uncguy85! Enjoy your 20's to the max--and travel is one of the most enjoyable ways to broaden horizons, meet interesting people, see amazing places and become exposed to exotic cultures...and that's just NYC --imagine outside of the US!
As you will probably be flying fares which earn 100%-150% EQMs, you theoretically can get to EXP by flying as few as 67K miles. Since you obviously have a lot of drive and energy, I predict that you will definitely make EXP in 2006! Have fun and spend a good deal of your weekends away from Chicago.