My single brother recently passed away. Being that he was very Private, I have yet to discover if he ever made out a will. Is there any way to find out? Maybe through the courts? He lived in Chicago.

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In my State POAs don't need to be filed. I wish they did.

As Florida said, call the Probate Office and see if Probate has been started. If so the Will is now Public Record.

If brother had assets and there is no one to handle them you can become Administrator to handle his finances. This will give you the ability to get bank records. Inform people of his death. Pay outstanding debts. If no beneficiaries the Courts will decide who receives his estate.
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If he had any property, there will have to be probate to transfer title.  Check on line with Cook County, see if anyone opened up probate.
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Were you close? Do you have access to his financial and legal papers? If so, you could go through them, for the last several years to see if there are any indications of having retained a law firm. If so, contact the law firm.

Are there any other survivors in your family who might know? You can also check the Chicago courts to see if any POAs were filed, and if so, and if the courts are open, ask to see them and check for any references to attorneys having prepared them.

Of, does he have a safety deposit box? If so, whatever bank he used would have a sign-up card which I'm assuming would reflect if he enabled access to anyone other than himself.

This is a difficult situation, and if you don't locate any end of life papers and he has assets, someone would have to follow intestacy (dying w/o a will) laws to take control and settle his estate.

Do you have any other siblings? His close friends?

I wish you luck on your search, and hopefully you'll find out something one way or the other, but I think the best way is to start with his financial records.
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