there should be some figs that will take chicago weather inground. majority of the figs we are growing do not need pollination. the type that need pollination will require fig wasp and outside of CA, i don't think there is any fig wasp in US. you can buy fig trees from jon (encanto farm so runs this forum), bass (trees of joy), ebay and other places. type of soil is lengthy subject. bigger the container the better, but it seems some do very well with 5 gal. i prefer 10 gal. but i heard 22 gal or bigger is preferred.
welcome to the forum.