CDL Jobs in Milwaukee, Wisconsin

Find truck driving opportunities in Milwaukee – Local, Regional, OTR & Owner Operator positions available.

Milwaukee CDL jobs remain among the most consistent in the Midwest, supported by the city’s industrial base and Great Lakes port access. Major routes along I-94 and I-43 connect Milwaukee to Chicago, Minneapolis, and Detroit, creating constant freight flow for manufacturing, retail, and food transport. CDL drivers in Milwaukee benefit from reliable pay, strong union representation, and opportunities across every major trucking segment.

Featured Opportunities

⭐ FEATURED

Empire National

Based in Chicago, IL

26FT Box Truck Owners

$4,000 - $8,000 a week Owner Operator

✓ Regional & OTR Routes ✓ Fuel discount ✓ No Forced Dispatch ✓ Weekly Settlements

Apply now →

⭐ FEATURED

TRANSGEORGIA LLC

Based in Chicago, IL

Owner Operators Needed – Cargo vans, sprinters & Large Box Trucks

$5,811 - $6,405 a week Owner Operator

✓ Consistent Work Next-Day Pay ✓ No Forced Dispatch ✓ Referral program Apply now →

Available CDL Jobs in Milwaukee, Wisconsin

Browse Local, Regional, OTR, and Owner Operator opportunities in Milwaukee

Route Type

Trailer Type

Salary Range

Company, Benefits, Features Search by company name, benefits, or job features

Class A Local P&D Driver (MKE)

Xpress Global Systems, LLC.

Milwaukee, Wisconsin $26.50 an hour Full-time

Drive local routes as a Class A Local P&D Driver with Xpress Global Systems, LLC. based in Milwaukee, WI 53224, where robust infrastructure and high freight density ensure a steady flow of work. Enjoy a competitive pay rate of $26.50 per hour while benefiting from home daily and convenient day shifts starting at 6 AM. With access to modern equipment and strong 24-hour dispatch support, your driving experience will be efficient and hassle-free.

View Job Details

TRUCK DRIVER / DEDICATED LANE / OTR / CDL A

Road Runners America Logistics LLC

Milwaukee, Wisconsin $2,200 - $3,500 a week Owner Operator

Drive success from Milwaukee with Road Runners America Logistics LLC, where owner-operators can earn up to $3,500.00 per week. This area boasts a robust network of freight opportunities and resources tailored for independent contractors. The community fosters strong connections, ensuring you have the support needed to grow your business. With a generous benefits package and a commitment to your success, this market is ideal for those looking to thrive locally.

View Job Details