I have a 99 dodge ram 2500 and i want to know if 37's will fit with a 2.5'' leveling kit up front.

 

No, you will need at least 8" lift.

 

I've got an 01 quad with a 6" and I run 35"s and at full lock they are VERY close to rubbing the fender- less than an inch.

 

on my 98, i have a 6in. lift with with 2in. taller springs also,
on a 16x8 wheel i could fit 38.5x11 tires
on a 16x10 wheel i can fit 35x12.50

if you ran a really skinny tire on a narrow wheel they might clear but i reall doubt it...