I don't know that you have a chance to grow any vine in there. The pots
are small for a vine, first of all. Second, you are right that you lose
a lot of zones when you leave plants in pots outside. Just to give you
an idea, I lost all the lemon balm that I had planted in a much larger
pot outside (2.5 feet in each direction), with good thermal contact to
the ground, and lemon balm is hardier than grapes (and I live near
Detroit, which is warmer than Chicago). But the jujube which is in the
pot survives and thrives to this day. So, I am guessing that anything
hardy to Zone 3 will survive - I know of no vines that hardy. Perhaps
an annual vine, such as sweet potato? That way you can change the soil
every year and have it prosper.