Guide

Starting a business in Chicago: the checklist

The steps come in a sensible order. You do not need to do everything in one week. Each step links to a free guide.

The order most new owners follow

1. Decide what you are selling and where. Online, at a market, from a storefront, or from home. This affects which licenses and taxes apply. How you structure the business is your decision. An attorney or CPA can advise you on it.
2. Form your business, if you choose to. If you pick an LLC, the Illinois filing fee is $150. What an LLC does and doesn’t do · What an Illinois LLC costs · Certificate of good standing. Doing business under a different name may need an assumed name filing.
3. Get your EIN. It is free from the IRS. How to get an EIN.
4. Open a business bank account. What to bring and ask.
5. Register for Illinois sales tax if you will sell taxable goods. It is free. Registration guide.
6. Get a resale certificate (CRT-61) if you buy inventory to resell. CRT-61 guide.
7. Check Chicago licensing. Do I need a business license? and home-based license.
8. Selling online? Sales tax across state lines and selling on eBay.
9. Compare platforms and set up your inventory. eBay vs Poshmark vs Depop, Form 1099-K and a simple SKU system.
10. Stay on schedule. Why compliance matters, the LLC annual report, and what to do if you fall behind.

Keeping a day job while you start

Many owners start part-time. See how Roth IRA rules work for new business owners.

Is this a business or a hobby?

If you are not sure, read hobby or business first. It explains what the IRS looks at.

Where I fit in

Everything on this site is free to do yourself. If the paperwork feels overwhelming, I help with the clerical and administrative work: the forms, the filing and keeping you on schedule. You make the decisions about how your business is set up.

I am not a CPA or an attorney

This page is general information, not legal or tax advice. Rules, fees and forms change, so confirm with the agency. For advice about your situation, talk to a CPA or an attorney.