Hi Chris I also have a Chicago Hardy and love it. I put in ground last when about 2 feet high got some figs but not ripe ones. I think you can put in ground now (dont wait any longer) it will give tree a chance to get established. If you do put in ground be sure to cover this winter. I already have some figs on mine right now and the tree really took off this spring. I live in Northern Delaware. Good Luck with the little guys
Bob

Chris another important point make sure to put in ground where the tree will get plenty of sun (6-10 hours) and is protected somewhat (wall, shed fence etc) if possible

Good Luck !
Bob

I have a hardy chicago in a 55 gallon drum and one in a 5 gallon bucket. The fig in the 5 gallon bucket has 11 figs on it. The other has more as it is much bigger. They taste great even though they were were no bigger than a grape.

don't overestimate the benefits of south wall planting. It is not what it is cracked up to be. See pic.
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Thanks,
I do want to plant one of them, but I'm thinking that the site I wanted up against the house (east) won't have enough sun. It's bright dappled light, but not direct sun due to trees. It would have had great wind protection there too.
I don't mind protecting. I'm going to be protecting some of my larger basjoo bananas this year too.

Like the basjoos, I've read where people say to plant deeper with figs.
How deep have others planted?

Thanks,
Chris

A fig tree ,may grow but cannot produce figs without a considerable amount light. If you can grow it in a bucket and place in a box gutter in full sun you will have a chance. My customer has a fig tree in broken light and it does not fruit.