As long as Chicago is still apart of the United States then yes free shipping=} As for will it fit your teenager probably not unless there head measures less than 19/20 inches=} Sorry I cant tell for sure if it will fit! Thanks for stopping!
Child size like 5- 12 yr old most likely will fit this just depends on the size of your head you want it on measures 10 inches flat about 20 inches round give or take a few because I left about 2 inches for a rim edge! =}