Riding dirty in Chicago?

Zak Rye /
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So I've recently from Ypsilanti Michigan to Chicago. Getting your bike legal here seems like a pretty massive undertaking in comparison to the old MI laws. My question-

Is it as difficult as it seems to get a kitted moped sans title registered in Chicago? The DMV website says I need a title, insurance, and a separate endorsement to ride legal here. That's a lot of cash and based on how strict they are on giving out driver licenses, I'm guessing it's a nightmare getting tags for an old non-stock moped.

...Which leads to my next question-

Is my best bet maybe to register my bike in MI or some other surrounding state? Anyone know how cool the cops are with that? Has anyone gotten pulled over for riding without any tags? I'm afraid mostly about getting my bike impounded or a huge fine.

Disclaimer- not asking anyone to promote anything illegal or suggest I break the law or anything. Just hoping to learn from other people's experiences with registering in IL, riding out of state tags, or riding non registered bikes in chicago.

Thanks!

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