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If your move was permanent, you should get a refund of all IL withholding after the move date. You file a part year resident IL return. You might get some push back from the IL tax agency if your W-2 show IL in box 15 and all your salary in box 16.
What's a permanent move? It depends on all the circumstances. Mainly that you didn't maintain an IL domicile and don't plan to return. Continuing to work for the same employer will complicate it.
https://www.grfcpa.com/resource/establishing-residency-for-state-tax-purposes/
Thank you so much for your reply. I just looked at my W-2 and it does show IL in Box 15.
My move was most definitely a permanent one. I made sure to change my address with USPS, updated my Voter Registration, got a Florida Drivers License, changed my address with my employer, etc ASAP upon relocating to Florida. I do work for the same Employer (company HQ is in NYC, I am a traveling sales rep/account manager and have never lived or worked in our NYC Headquarters)
I have been using the Free DIY turbotax option for years b/c I haven't had any special circumstances, and filing a simple tax return with one W-2 was all I have ever needed. I did pay for one of their premium tax filing option this year, knowing that I would need additional help. Planning on utilizing the assistance they provide with the plan I purchased to obtain additional instruction on how to remedy this. Hoping they can help!
It's sounds like you are on solid ground. You may only need to attach a statement of explanation ("permanent move but I forgot to change my state withholding with my employer').
"my Boss had mentioned that he believed that since I resided the majority of 2021 in Florida, I would qualify to get a return of all taxes paid while living in Chicago, Illinois"
That's not correct. All your income prior to your becoming a FL resident is taxable by Illinois. You became a FL resident for tax purposes on the day you began living there with the intent to make it your permanent residence. As @Hal_Al mentioned, you must file a part-year resident Illinois tax return for 2021.
Also: did you physically work in Illinois after you became a FL resident? If so, that income would also be taxable by IL.
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