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My guess is he really likes you, but he doesn't want history to repeat itself where you guys end up breaking up over distance again. Would you really leave Chicago and move for him? He's probably think there's just no point in pursuing things any further. Long distance is hard. I spend a lot of time away from my boyfriend. We don't live in the same city right now but we don't usually have to go more than a week and a half without seeing one another and I'm definitely okay with leaving my current location to be with him.
You can either let it go and accept he's fading out, or you can flat out ask him what's going on.
You've mentally and emotionally jumped ahead about dozen steps in this relationship. And his ACTIONS speak volumes right now.
Timing is important when it comes to love, and you two just might be victims of bad timing. Live your life, and if he becomes a part of it, great. But I would not force it. His hesitation is serving a very important purpose. He's doing the right thing by paying attention to his gut, which apparently is giving him a few warnings about what it would take to pursue this relationship.
Pay attention to your instincts too instead of your fantasies.
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