Self-employed and 1099 contractors
Tax Help for Self-Employed and 1099 Workers in Chicago
Schedule C, quarterly estimates, mileage
What this business files
Form numbers and dates. A deadline landing on a weekend moves to the following Monday.
- Schedule CProfit or loss from the work, filed with the personal returnApril 15
- Schedule SESelf-employment tax, covering Social Security and MedicareWith the return
- Form 1040-ESQuarterly estimated payments, federal and IllinoisApril 15, June 15, September 15, January 15
- Form 1099-K and 1099-NECStatements from platforms and clients, matched against your own recordsArriving in January and February
Where owners lose money
We watch for these on every file in this trade.
- Self-employment tax is roughly 15.3% on net profit and sits on top of income tax. Setting aside only the income tax leaves a shortfall every April.
- The mileage deduction needs a log with dates and purpose. A year-end total taken from an app with no trip detail rarely survives a question.
- Platform 1099-K thresholds have changed twice since 2022. We check the current rule against your platform statements rather than the number you remember.
- A home office deduction has a strict exclusive-use test, and claiming it on a kitchen table is not worth the exposure.
Services this trade uses
One fixed monthly fee, agreed before the first month. Catch-up on prior periods is quoted once.
Self-employed or 1099
Common questions
How much should I set aside from each payment?
Between 25% and 30% of net profit covers federal income tax, Illinois income tax and self-employment tax for most people at this income level. We set the exact figure from your own numbers after the first quarter and adjust as the year runs.
What do I need to claim mileage?
A log with the date, the destination and the business purpose of each trip. Rideshare platforms produce online miles, and the trip to the first pickup and home from the last one usually count as well when the log supports them.
I missed my quarterly payments. What now?
Pay as soon as you have the money, since the underpayment penalty accrues by the day. Making the remaining quarters larger reduces the total. We calculate what to send now and what to send in January.
Should I form an LLC?
An LLC gives liability separation and changes nothing about the tax by itself. The saving comes from an S corporation election, and the election starts paying off once net profit is steady around $60,000 or more. Below that, the payroll and filing cost outweighs the benefit.
Get your price this week
The first conversation is free. We read three months of statements, quote a flat figure and hold it. We reply the same working day.