Frequently Asked Questions

  • Here is a checklist of common documents and information you may need when filing taxes:

    1. Social Security Number (SSN) or Individual Taxpayer Identification Number (ITIN) for yourself and any dependents.

    2. W-2 forms from all employers you worked for during the tax year.

    3. 1099 forms if you received income from sources other than employment, such as freelance work or interest income from a bank account.

    4. Form 1098 if you paid mortgage interest on a home you own.

    5. Records of any additional income, such as rental income, business income, or capital gains.

    6. Records of any deductions you plan to claim, such as charitable contributions or medical expenses.

    7. Form 1095-A if you received health insurance through the Marketplace.

    8. Any documents related to retirement accounts, such as Form 1099-R or Form 5498.

    9. Receipts for any educational expenses or student loan interest paid.

    10. State and local tax forms (such as a W-2G, 1099-G, or 1099-MISC) if applicable.

    11. Information related to any estimated tax payments made throughout the year.

    12. Any previous year tax returns, if applicable.

    It's always a good idea to double-check the IRS website for any additional requirements that may apply to your specific tax situation, and Painless Tax will reach out with any additional needs.

  • Our menu pricing is straightforward, so you’ll know exactly what you’ll pay before you hire us.

  • Nope. We stick to our menu pricing, even if your return is more complex than we imagined.

  • Painless Tax Solutions eliminates the stress in a way other firms just don’t. Our menu pricing means you’ll never get an unexpected bill, while our friendly, hassle-free process gets your taxes filed timely and pain-free.

    But the thing that really sets us apart? We don’t disappear after tax season. We look beyond April 15, offering advice and techniques to help you save money down the line.

  • You can use our secure portal to upload all necessary documents! You can also mail them to our locations in Illinois and Wisconsin, or drop them off in-person, by appointment.

  • Our professional preparers take every precaution to ensure that your documents and information are protected, and our online portal is a secure space to safely store your private financial details.

  • Most returns are processed within a week.

  • It’s possible that your return is still being processed by the IRS. Processing times vary, depending on the time of year and the complexity of your return. You can check the status of your return online using the Where's My Refund? tool on the IRS website.