Owner Operator & Lease Purchase in Milwaukee, WI — Now Hiring

As of October 2026, there are 9 owner operator & lease purchase openings in Milwaukee, WI. Local pay ranges from $2,300 to $130,000/year. Listings are updated daily — many roles offer flexible hours and employee discounts.

Auto Logistics Pros

Independent Contractor Driver - Auto Parts Courier

Milwaukee, WI

$2,800 - $4,800

Final Mile Delivery Co.

Independent Contractor Driver - Final Mile Parcel

Milwaukee, WI

$3,000 - $5,500

Urban Pedal Logistics

Independent Contractor Driver - Urban E-Bike/Scooter Courier

Milwaukee, WI

$2,700 - $4,860

Local Merchant Delivery Network

Independent Contractor Driver - Early Morning Bakery/Floral

Milwaukee, WI

$2,640 - $4,620

Regional Expedite Logistics

Independent Contractor Driver - Long Distance / Regional Courier

Milwaukee, WI

$3,220 - $5,520

On-Demand Tasks Network

Independent Contractor Driver - On-Demand Errands (TaskRabbit/Roadie)

Milwaukee, WI

$2,300 - $4,600

Secure Document Couriers

Independent Contractor Driver - Night Shift Legal/Document Courier

Milwaukee, WI

$2,800 - $5,000

Corporate Catering Couriers

Independent Contractor Driver - Catering Logistics

Milwaukee, WI

$3,920 - $6,720

Hot Shot Transportation Co.

Hot Shot Truck Driver - Owner Operator with 1 Ton Pickup

Milwaukee, WI

$85,000 - $130,000

Owner Operator & Lease Purchase in Milwaukee — FAQ

How many owner operator & lease purchase jobs are open in Milwaukee, WI?
There are currently 9+ owner operator & lease purchase in Milwaukee, WI. New owner operator & lease purchase roles are added regularly — check this page for the latest openings.
How much do owner operator & lease purchase jobs pay in Milwaukee?
Pay for owner operator & lease purchase in Milwaukee varies by employer, equipment and how much time you spend away. Many positions offer flexible scheduling and employee discounts, and some include shift differentials for nights and weekends. Browse the listings above to see pay details for each opening.
Do these owner operator & lease purchase positions require experience in Milwaukee?
Many owner operator & lease purchase positions in Milwaukee require no prior experience, and most employers provide paid on-the-job training. Check individual listings for specific requirements.
How do I apply for owner operator & lease purchase jobs in Milwaukee?
Browse the 9+ owner operator & lease purchase listings above, click on any position for full details including pay and shift times, then follow the application link to the employer. Most driver applications take about 10–20 minutes online.

Owner Operator & Lease Purchase in Other Cities

Owner Operator & Lease Purchase in New York

9 open positions

Owner Operator & Lease Purchase in Los Angeles

18 open positions

Owner Operator & Lease Purchase in Chicago

9 open positions

Owner Operator & Lease Purchase in Houston

9 open positions

Owner Operator & Lease Purchase in Phoenix

9 open positions

Owner Operator & Lease Purchase in Philadelphia

9 open positions

Owner Operator & Lease Purchase in San Antonio

9 open positions

Owner Operator & Lease Purchase in San Diego

9 open positions

Owner Operator & Lease Purchase in Dallas

9 open positions

Owner Operator & Lease Purchase in Fort Worth

9 open positions

Other Driving Careers in Milwaukee

Part-Time Driving Jobs in Milwaukee

25 open positions

Delivery Driver Jobs in Milwaukee

21 open positions

Full-Time Driving Jobs in Milwaukee

19 open positions

Weekend Driving Jobs in Milwaukee

9 open positions

CDL-B Driving Jobs in Milwaukee

7 open positions

Regional Driving Jobs in Milwaukee

7 open positions

CDL-A Truck Driving Jobs in Milwaukee

5 open positions

Night Shift Driving Jobs in Milwaukee

5 open positions

Last updated: October 28, 2026