I’ve spent more than ten years practicing immigration law in Illinois, and a large portion of my work has involved serving as a naturalization lawyer in Chicago, IL for people who assumed citizenship would be the easiest step of their immigration journey. In reality, naturalization is often where years of small decisions—travel choices, tax filings, old arrests, even casual paperwork errors—suddenly matter a great deal. Chicago is not a place where those details get overlooked.
One case that still sticks with me involved a long-time permanent resident who had done everything “right” by their own understanding. Stable job, family, no recent legal trouble. During our review, we discovered several extended trips abroad taken years earlier to care for a sick relative. None of them were malicious or hidden, but together they raised questions about continuous residence. If we had rushed the filing, that history would have come up cold in the interview. Instead, we took time to document the purpose of the travel and prepare a clear explanation. The interview still required careful handling, but it didn’t turn adversarial.
Another situation I’ve seen repeatedly involves old criminal records that applicants believe were sealed, expunged, or simply too minor to matter. I once worked with someone whose only issue was a decades-old misdemeanor that never resulted in jail time. At the citizenship interview, that incident became the main focus. Because we had already pulled court records and discussed how to address it honestly, the conversation stayed controlled. I’ve seen similar cases go sideways when applicants were advised to “just answer if asked” without preparation.
Chicago USCIS interviews tend to be thorough, especially around good moral character, tax compliance, and prior immigration filings. I’ve prepared clients who were surprised by how much time officers spent reviewing employment history or past petitions, even those filed many years earlier. Attorneys who regularly handle naturalization cases here understand that the interview is rarely a formality. Preparation isn’t about rehearsing answers; it’s about making sure the record supports them.
One of the most common mistakes I encounter is filing too early. People hit the eligibility date on the calendar and want to submit immediately, even if there are unresolved issues that would benefit from time and cleanup. In my experience, waiting a few extra months to strengthen a case is often far better than filing quickly and inviting unnecessary scrutiny. Citizenship is permanent, and a denial can reopen questions people thought were long settled.
After years of handling naturalization cases in Chicago, I’ve come to see citizenship less as a finish line and more as an audit of a person’s entire immigration history. The lawyers who do this work well are the ones who slow the process down, ask uncomfortable questions early, and prepare clients for how closely their stories will be examined. That measured approach doesn’t make the process feel faster, but it does tend to keep it on track.