i have a love hate relationship with chicago i love it because its a great city, hate because of its weather. summers are great but winters are deadly. this fall was terrible but yeah...., soo how is it in your city?
I actually like New York. If you know your way around, you can find some pretty nicely paved roads to ride on, local neighborhoods have some pretty good hills and you occasionally run into a few fellow skaters along the way. Best of all, the longboard shops are great here!