Milwaukee, WI
Looking for regional CDL-A work around Milwaukee? Here's the pay, the home time, and a fast way to get matched with carriers hiring right now.
Milwaukee sits at the junction of I-94 and I-43 on Lake Michigan, where Port Milwaukee moves about 2.3 million metric tons of cargo annually and two Class I railroads link the Upper Midwest to national markets.
Runs within a multi-state region (typically a 500–1,000 mile radius), balancing solid weekly miles with more predictable home time than OTR. For CDL-A drivers based in Milwaukee and nearby communities like Oak Creek, Franklin, Waukesha, that translates to steady freight and regional runs you can actually build a schedule around.
Regional CDL-A pay in this market typically runs about $67k to $88k a year for company drivers, before sign-on bonuses, detention, and per diem. The number that matters most is weekly miles times your rate — a strong rate on thin miles loses to a steady seat every time.
Most regional CDL-A work here moves dry van and reefer for the region's retail, grocery, and manufacturing shippers, with flatbed and tanker available for drivers who want a pay premium and have the endorsements.
Wisconsin rates run about 1% below the national average for the same freight, which is baked into the numbers below. Figures assume 2,250 paid miles a week (typical for regional out of Milwaukee) plus ~7% in accessorials (detention, stop pay, per diem), over 50 working weeks.
| Experience | Rate (typical–good) | Weekly gross | Annual |
|---|---|---|---|
| 1–2 years | $0.55–0.61/mi | $1,335–$1,478 | $66,736–$73,886 |
| 2–5 years | $0.59–0.66/mi | $1,430–$1,597 | $71,503–$79,845 |
| 5+ years | $0.64–0.73/mi | $1,549–$1,764 | $77,461–$88,187 |
From the CDL Lane pay model — cents-per-mile researched across 100+ carriers (how we calculate), adjusted for Wisconsin. Run your own numbers in the pay calculator.
Tell us your experience, freight, and schedule. We'll line up regional carriers hiring near Milwaukee — free, fast, no obligation.
Get matched →Regional CDL-A drivers in the Milwaukee market typically earn $67k–$88k a year, with the exact number driven by experience, weekly miles, and freight type — the table above breaks it down by experience band.
That's the standard: a 500–1,000 mile radius with weekly home time, usually weekends. Confirm the exact home-time policy with each carrier in writing — "most weekends" and "every weekend" are different jobs.
A valid CDL-A and a reasonably clean driving record cover most openings. Tell CDL Lane your experience, preferred freight, and home base and we'll match you with carriers hiring near Milwaukee — including Oak Creek, Franklin, Waukesha.