Wow, this is a frustratingly difficult question to answer. It just doesn't seem like Chicago bakeries are very friendly to those who can't eat sugar. If you can actually find a sugar-free pie at Jewel, you might have to go with that.
I did find this place, which will ship a sugar-free pumpkin pie, but they need a few days' lead time:
http://www.serendipitiessweets.com/pie.htmAre you just trying to avoid added sugar, or is your recipient a diabetic trying to manage their condition via diet? I ask because pumpkin and pie crust by themselves are relatively carby, so even if there's no sugar, they might not be able to enjoy it.
Good luck tracking this down! And if you find a bakery specializing in sugar-free or carb-free items, please come back here and let me know. Thanks!
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