Milwaukee is more than just beer, brats, and the Brewers. It’s also a major hub for transportation and logistics, making it a prime location to begin or advance your truck driving career. With its access to major highways, growing demand for freight movement, and abundance of trucking companies hiring, Milwaukee offers excellent opportunities for both new and experienced drivers.
Whether you’re just getting your CDL or you’re a seasoned pro looking for a better route, this guide covers everything you need to know about the top truck driving jobs in Milwaukee—where to start, what to expect, and how to land a job with one of the city’s most trusted carriers.
One company standing out in the region is Service One Transportation, Inc., offering competitive pay, modern equipment, and a driver-first culture. If you’re ready to take the next step, Apply Now and explore available CDL positions in the Milwaukee area.
Why Milwaukee Is a Prime City for Trucking Careers
Milwaukee’s central location in the Midwest makes it a strategic logistics hub. Interstate highways like I-94, I-43, and I-41 converge in the area, providing direct access to Chicago, Minneapolis, and Detroit. With Lake Michigan to the east and growing industrial centers nearby, Milwaukee serves as a key shipping point for freight moving throughout the region.
This results in several career advantages for truck drivers in Milwaukee:
- Access to regional and long-haul routes
- Steady freight demand year-round
- Diverse job types including dry van, reefer, flatbed, and intermodal
- Competitive wages due to the strong labor market
- Cost of living lower than in many other metro areas
What Kind of Truck Driving Jobs Are Available?
Truck drivers in Milwaukee can choose from a wide range of job types depending on their preferences, endorsements, and experience level. Here’s a breakdown of what’s typically available:
Local CDL Jobs
Local driving jobs are ideal for drivers who want to be home daily. These routes often involve pick-ups and deliveries within a 100-mile radius of Milwaukee.
Pros:
- Daily home time
- Predictable hours
- Great for family life
Cons:
- Lower average pay compared to OTR
- More frequent loading/unloading
Regional Routes
Regional jobs cover Wisconsin and surrounding states like Illinois, Minnesota, and Michigan. Drivers are usually home on weekends or every few days.
Pros:
- Higher pay than local jobs
- Balance of home time and mileage
- Steady work
Cons:
- Occasional overnights away from home
Over-the-Road (OTR) Positions
OTR drivers run long-haul routes across the U.S. These jobs offer the highest earning potential and are great for drivers who enjoy the open road.
Pros:
- Top pay
- Bonus opportunities
- See the country
Cons:
- Extended time away from home
- Less predictable schedule
Owner Operator and Lease Purchase
Many Milwaukee trucking companies, including Service One Transportation, work with independent contractors or offer lease-to-own truck programs. If you have the ambition to run your own business, this is a great path.
Pros:
- Greater earning potential
- More freedom and flexibility
- Build your own brand
Cons:
- More financial risk
- Responsible for truck maintenance and insurance
Average Pay for Truck Driving Jobs in Milwaukee
Driver compensation in Milwaukee varies based on experience, endorsements, equipment type, and route category. However, here are the average pay ranges:
| Driver Type | Average Annual Pay |
| Entry-Level CDL Driver | $48,000 – $55,000 |
| Regional Driver | $60,000 – $70,000 |
| OTR Driver | $70,000 – $85,000 |
| Owner-Operator | $100,000+ |
Companies may also offer performance bonuses, referral bonuses, detention pay, layover pay, and more. Some include paid orientation and sign-on bonuses to attract qualified drivers.
What Sets Top Trucking Companies Apart?
While pay is a major factor when choosing where to work, many drivers also consider benefits, company culture, and equipment quality. When evaluating potential employers in Milwaukee, look for these qualities:
- Modern equipment with safety features and comfort upgrades
- Reliable dispatch team that respects your time
- Flexible home time and route options
- Health insurance, 401(k), and PTO
- Stable freight contracts with consistent miles
- Strong safety record and compliance focus
Companies like Service One Transportation pride themselves on treating drivers like family, offering open communication, and maintaining high retention through respect and reliability.
Starting Your Trucking Career in Milwaukee with No Experience
If you’re just starting your CDL career, Milwaukee offers several training schools and carriers that work with new graduates. Here’s what to do:
- Choose a certified CDL school – Look for one with high job placement rates and solid equipment
- Pass the written and road tests – Earn your CDL-A license
- Apply to entry-level positions – Many companies offer finishing programs or mentorships
- Focus on safety and performance – Build your record for access to premium routes and higher pay
Service One Transportation also considers new drivers who demonstrate strong safety awareness and a professional attitude.
Lifestyle and Work-Life Balance as a Milwaukee Truck Driver
One of the best things about driving out of Milwaukee is the flexibility in lifestyle. Whether you want to be home every night or you’re chasing high-mileage OTR runs, there’s a role for you.
The city itself also offers truckers a solid support system with accessible truck stops, repair shops, rest areas, and staging yards. Combined with a lower-than-average cost of living, Milwaukee is a great place to build a stable income and enjoy a balanced life.
Tips for Landing the Best CDL Jobs in Milwaukee
- Clean up your driving record – Companies look closely at your motor vehicle report (MVR)
- Add endorsements – Hazmat and Tanker can boost your earning potential
- Apply to companies that match your values – Pay, home time, equipment, and respect all matter
- Follow up – After applying, call the recruiter to introduce yourself
- Stay compliant – Understand hours-of-service rules and safety protocols
Final Thoughts: Launch Your Career with a Company That Puts Drivers First
Milwaukee continues to grow as a transportation hub, offering high-quality CDL jobs across local, regional, and national routes. With the right mindset and a reliable carrier, your trucking career can take off quickly and sustainably.
Service One Transportation, Inc. is one of the top-rated employers in the region, known for supporting drivers with competitive pay, modern equipment, and a personal approach to management. Whether you’re a rookie or a seasoned driver, this is a company where your efforts are recognized and rewarded.
If you’re ready to get started or switch to a company that truly values drivers, visit https://www.serviceonetransportation.com/cdl-jobs-milwaukee/ and explore available CDL positions in Milwaukee today.