Planning an Appalachian Trail trip.?

I want to do a backpacking trip with me and my buddy. I'm thinking that I would like to do around two weeks on somewhere in the southern portion of the trail. I'm in good shape so I'm not worried about how hard the hiking is however I am relatively new to backpacking so I would like somewhere that I could get help if I need it but I would also like some solitude. My two questions would be what is a good place for me to hike and how is the best way for me to get there. I would be willing to travel there in really anyway weather it's driving flying or taking a train or any combination. I live in chicago area thanks.