I moved your question to business law; however, you should speak with an attorney who has experience with both business/corporate matters and tax matters because the primary issues here will be tax-related.
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You ask if it is possible in Illinois to establish an LLC and designate it as a shareholder (you call it a "member") in an S-Corporation. The short answer is, an S-Corp. must have natural persons as its shareholders. However, an LLC can - and they often do - have an S-Corp as a member.
You also ask what kind of lawyer you should consult. I do not think it is necessary to consult a tax lawyer for the limited purpose you describe. Instead I believe you should find a competent business lawyer and bring in outside professionals to augment that lawyer's services.
The best corporate counsel are not only Attorneys but Quarterbacks (if you will) - they can see the big picture and bring additional professionals to bear as needed to meet the goals of their Client.
I have linked to some of the relevant sections of my website below. Feel free to take a look and contact our office if we can be of assistance. In any event, I hope that this information has been helpful and wish you the best.
I do agree with both previous answers. And I think that you should seek advice by starting with the overall results you're seeking to accomplish. Instead though, it seems that you are concentrating on implementing the vehicles you believe are necessary.
Like I said, I agree. You should get an attorney to quarterback this process for you.
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