Regional Driving Jobs in Milwaukee, WI — Immediate Openings

As of October 2026, there are 7 regional driving openings in Milwaukee, WI. Local pay ranges from $3,000 to $130,000/year. Listings are updated daily — many roles offer flexible hours and employee discounts.

Regional Expedite Logistics

Independent Contractor Driver - Long Distance / Regional Courier

Milwaukee, WI

$3,220 - $5,520

Regional Expedite Logistics

Evening Role:Driver Opportunity(Milwaukee)

Milwaukee, WI

$3,500 - $6,000

Nightline Freight

Driver Opportunity(Part-Time)@ Nightline Freight-Milwaukee

Milwaukee, WI

$3,600 - $5,200

Carquest Auto Parts

Milwaukee Flexible Job:Carquest Regional Parts Transfer Driver

Milwaukee, WI

$3,400 - $5,000

Regional Auto Dealership Group

Flexible Gig:OEM Dealership Auto Parts Delivery Driver(Milwaukee)

Milwaukee, WI

$3,000 - $4,500

Hot Shot Transportation Co.

Hot Shot Truck Driver - Owner Operator with 1 Ton Pickup

Milwaukee, WI

$85,000 - $130,000

Foremost Transport

Mobile Home Transport Driver - CDL A Oversize Load

Milwaukee, WI

$82,800 - $110,400

Regional Driving Jobs in Milwaukee — FAQ

How many regional driving jobs are open in Milwaukee, WI?
There are currently 7+ regional driving in Milwaukee, WI. New regional driving roles are added regularly — check this page for the latest openings.
How much do regional driving jobs pay in Milwaukee?
Pay for regional driving 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 regional driving positions require experience in Milwaukee?
Many regional driving 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 regional driving jobs in Milwaukee?
Browse the 7+ regional driving 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.

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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

Owner Operator & Lease Purchase in Milwaukee

9 open positions

Weekend Driving Jobs in Milwaukee

9 open positions

CDL-B 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