Chicago Trucking Tax Prep, Bookkeeping & Accounting Services
Reliable financial management for truck drivers, owner-operators and trucking companies. We keep your books clean, track every deduction and file accurate returns so you can stay focused on the road.
Built around how trucking works
- Load income matched to your settlements
- Fuel, repairs and tires categorized
- Per diem days tracked for meal deductions
- Form 2290 and truck depreciation handled
- Mileage and fuel records ready for IFTA
- Quarterly estimated taxes planned ahead
Certified on the platforms our clients use
Keep more of every load you haul
Trucking businesses operate with constant financial activity, from fuel expenses and maintenance costs to load payments and operational overhead. Without organized bookkeeping and accurate tax reporting, it becomes difficult to track profitability and stay compliant.
Heard & Associates LLC provides trucking tax preparation and bookkeeping for owner-operators and trucking companies across Chicago. We keep your records accurate all year, so tax time is about filing, not digging through receipts from the cab.
Our goal is simple: you stay focused on operations while your books and tax filings stay organized and compliant.
Tax and bookkeeping services for truckers
Whether you run one truck under your own authority or manage a small fleet, we handle the numbers so you can handle the road.
Trucking Bookkeeping
We record and categorize load payments, fuel, repairs, insurance and every other transaction, so you always know what each truck is really earning.
Bookkeeping services →Owner-Operator Tax Preparation
Self-employment income, settlements, per diem and truck depreciation reported correctly on your personal return, with every deduction you are entitled to.
Income tax preparation →Trucking Company Tax Returns
Partnership, LLC and corporate returns for carriers running multiple trucks and drivers, prepared from clean books and filed on time.
Business tax preparation →Quarterly Estimated Taxes
Nothing is withheld from your settlements. We calculate quarterly payments so you are not hit with a large bill and penalties in April.
Tax advisory →Bank and Card Reconciliation
Fuel cards, business accounts and factoring statements matched to your books so nothing is missed or counted twice.
Reconciliation services →S Corp Setup and Returns
When profit grows, an S corporation can cut self-employment tax. We run the numbers, set it up and handle the 1120-S each year.
S corp tax preparation →Common trucking deductions we track
Trucking businesses carry significant expenses, and every one of them needs a record. We track these all year so they are ready to claim when your return is prepared.
- Fuel, oil and DEF
- Repairs, maintenance and tires
- Truck and trailer depreciation, including Section 179
- Insurance, permits and licensing fees
- Heavy vehicle use tax (Form 2290)
- Tolls, scales and parking
- ELD, phone, dispatch and load board fees
- Per diem meals while on the road
Per diem for truck drivers
The IRS special per diem rate for transportation workers traveling in the continental U.S. Drivers subject to DOT hours-of-service rules can generally deduct 80% of it, instead of the usual 50% for meals.
The key is a record of every day away from home. We show you what to keep and apply it correctly on your return.
Check my deductions →Deadlines owner-operators cannot miss
Owner-operators pay self-employment tax on top of income tax, and no one withholds it from your settlements. That makes planning ahead essential. Quarterly estimates spread the bill across the year instead of leaving one large payment for April.
Trucking also has its own filings. If you run interstate under your own authority, your IFTA fuel tax reports depend on accurate mileage and fuel records. Heavy trucks also owe the federal heavy vehicle use tax on Form 2290. We keep your books organized around these dates so the numbers are ready when you need them.
How we work with truckers
Our structured onboarding ensures every client starts with a clear financial system and organized records.
Discovery
We learn how you operate: your authority, trucks, settlements and where your records stand.
Proposal
You get a clear scope covering bookkeeping, returns and quarterly planning.
Setup
We connect your accounts and fuel cards and set up categories built for trucking.
Year-round support
Monthly books, quarterly estimates and a tax-ready file when the year closes.
What to look for in a trucking tax specialist
A general preparer can file a return. A trucking-focused team makes sure nothing is left on the table.
Industry understanding
Accurate reporting
Year-round planning
Reliable communication
Secure handling
Rated 5.0 by 100+ clients on Google
Owner-operators and small business owners trust us to keep their books accurate, explain the numbers clearly and answer quickly.
Trucking tax questions
Every operation is different. If your question is not here, ask us during a consultation.
Book a consultation →What can truck drivers deduct on their taxes?
Owner-operators can generally deduct ordinary business costs such as fuel, repairs, tires, insurance, permits, tolls, scales, parking, ELD and phone costs, load board fees, the heavy vehicle use tax and depreciation on trucks and trailers. Per diem meals while away from home are also deductible within IRS limits.
How does per diem work for truck drivers?
Instead of saving every meal receipt, drivers can use the IRS special transportation rate, currently $80 per day within the continental U.S. Drivers subject to DOT hours-of-service rules can generally deduct 80% of that amount. You still need a record of the days you were away from home overnight.
Can a company driver deduct trucking expenses?
If you are a W-2 company driver, unreimbursed job expenses are generally not deductible on your federal return. Owner-operators who receive a 1099 or run their own authority can deduct business expenses. We help you understand which situation applies to you.
Do owner-operators need to pay quarterly taxes?
Usually yes. Because nothing is withheld from settlements, the IRS expects estimated payments in April, June, September and January. Missing them can lead to penalties. We calculate the amounts and remind you before each due date.
What is Form 2290?
Form 2290 reports the federal heavy vehicle use tax on trucks with a taxable gross weight of 55,000 pounds or more. For trucks on the road in July, it is generally due by August 31. The tax paid is a deductible business expense.
What is IFTA and do I need it?
The International Fuel Tax Agreement lets interstate carriers report fuel tax to their home state, which then shares it with the other states driven in. Illinois-based carriers with qualifying vehicles file quarterly reports. Accurate mileage and fuel records are what make those reports easy.
Should my trucking business be an S corp?
It can make sense once your profit is high enough that payroll tax savings outweigh the added costs of payroll and a separate return. We compare your options with your real numbers. Learn more about S corp tax preparation.
Do you only work with Chicago truckers?
No. We are based in the Chicago area and work with drivers and carriers throughout Illinois. Most of our work is handled securely online, which suits drivers who are on the road most of the week.
Keep your trucking finances on track
If you are a truck driver or run a trucking business, book a consultation and we will review your books, deductions and tax setup.