Chicago EA Guide: Three-State Commutes, Trades, and Small-Business Returns
Last reviewed: 2026-07-21. Local claims below link to the agency or public dataset that owns them.
“Chicago client” is not a complete location. The person may live in northwest Indiana, work in the Loop, spend two days a week in Wisconsin, and run a weekend business from home. Before software, the preparer needs a map, a calendar, and a list of every jurisdiction on the wage statements.
Read the metro as a border region
Chicago's finance and professional-services core sits beside logistics, manufacturing, health care, and the trades. The BLS Chicago area release is a sober place to inspect employment and wages. It does not establish a preparer shortage, and it should not be used to promise a salary.
A useful Chicago practice set
- An Indiana resident with Illinois wages, remote-work days, and withholding that may not match the final sourcing analysis.
- A union tradesperson with multiple W-2s, tool purchases, travel, and a side contracting activity that must not be blended together.
- A neighborhood retailer or restaurant owner whose federal books need to reconcile to Illinois and Chicago records.
City and state questions need different owners
Use the Illinois Department of Revenue for Illinois income and business-tax guidance and the Chicago Department of Finance for city-administered taxes. Do not publish blanket preparer-registration claims without an agency rule that actually supports them.
Earn complexity a layer at a time
- Master federal wage, Schedule C, depreciation, and basis rules before adding multistate returns.
- Review Illinois resident and nonresident instructions with a blank paper allocation schedule beside you.
- Seek supervised seasonal work or VITA experience, then add one neighboring-state pattern only after a reviewer signs off.
Chicago reference shelf
- Illinois individual income tax — forms and current guidance.
- Chicago business taxes — city tax information.
- Illinois SBDC — public business advising.
- IRS worker-classification guidance — federal starting point.
- EA Dojo business practice — drill entity and business rules.
The federal checkpoint before you book anything
The testing administrator changed in 2026, so skip old testing-vendor walkthroughs. Start with the IRS EA FAQ, then confirm the current scheduling link, test window, fees, and identification rules there. Use the EA cost breakdown for a line-item budget and free verified practice to find the rules you actually need to repair.
For Chicago work, geographic precision is professional kindness. Ask where the person lived and worked before asking what forms last year's software produced.