Florida is going to want you to pay the sales tax in Florida (and, of course, Illinois is going to want you to pay the sales tax in Illinois). If you immediately register the car in Florida, you are going to have to pay sales tax there (and can probably get out of paying it in Illinois). If you register it in Illinois first, then you'll probably have to pay tax in both locations.
The only state I definitively know the rules for is Massachusetts, where you must pay sales tax on any car you have owned for less than a year when you first register it there. They tried to make me pay sales tax on my car in MA when I moved there since I was registering it in February 1992 and had purchased it in February 1991, but fortunately the specific dates of purchase showed I'd owned it for 367 days, and I got out of paying the sales tax.
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