Some parts of Chicago are very similar to my climate, if they get the cool lake breezes. I would second the recommendations for Sweet Chocolate and Elephant Ear... very prolific, and ripen early. Melrose is another short DTM pepper, fairly thin walls, but sweet & crunchy ripe, and high yielding.
For hot peppers, Beaver Dam would be my best recommendation; large thick-walled peppers borne abundantly on compact plants, and a short DTM. I have also had good results with the heirloom Italian Cheese.
There are two varieties that ripen slowly, but would give you early loads of immature peppers. Cubanelle is a large sweet "frying" type, and bears very heavily - so heavily that support would probably be necessary. Pelso is a hot pepper that is white immature, borne upright, and has an early, heavy set on very compact plants.
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