As an update, it looks like outdoor dining may be allowed by the beginning of June. But be aware that demand will be hundreds of times greater than supply, if not thousands.
The governor has said that IL won't "return to normal" until there's a vaccine or a cure. If he sticks to that, IL and MI will probably be two states to avoid for the next year as they have the strictest regulations during the lockdown. Unfortunately I live in one and vacation in the other...