OTR & Long Haul Jobs in Milwaukee, WI — Start This Week

As of October 2026, there are 8 otr & long haul openings in Milwaukee, WI. Local pay ranges from $72,000 to $345,800/year. Listings are updated daily — many roles offer flexible hours and employee discounts.

Schneider National

CDL A Truck Driver - OTR Dry Van

Milwaukee, WI

$78,750 - $100,800

Crete Carrier

CDL A Truck Driver - Regional Dry Van Home Weekly

Milwaukee, WI

$72,000 - $92,000

CRST The Transportation Solution

CDL A Truck Driver - OTR Team Driver

Milwaukee, WI

$86,500 - $110,000

Hora Express

CDL A Owner Operator Truck Driver - 91% Pay

Milwaukee, WI

$247,000 - $345,800

Black Eagle Express

CDL A Truck Driver - OTR Flatbed Conestoga

Milwaukee, WI

$109,200 - $136,500

Quantix

CDL A Truck Driver - Regional Liquid Tanker Hazmat

Milwaukee, WI

$90,000 - $110,000

Shaffer Trucking

CDL A Truck Driver - OTR Refrigerated Reefer

Milwaukee, WI

$80,000 - $95,000

Jack Cooper Transport

CDL A Truck Driver - Auto Hauler Car Transport

Milwaukee, WI

$95,000 - $135,000

OTR & Long Haul Jobs in Milwaukee — FAQ

How many otr & long haul jobs are open in Milwaukee, WI?
There are currently 8+ otr & long haul in Milwaukee, WI. New otr & long haul roles are added regularly — check this page for the latest openings.
How much do otr & long haul jobs pay in Milwaukee?
Pay for otr & long haul 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 otr & long haul positions require experience in Milwaukee?
Many otr & long haul 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 otr & long haul jobs in Milwaukee?
Browse the 8+ otr & long haul 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

20 open positions

CDL-A Truck Driving Jobs in Milwaukee

10 open positions

Full-Time Driving Jobs in Milwaukee

9 open positions

Delivery Driver Jobs in Milwaukee

8 open positions

Weekend Driving Jobs in Milwaukee

5 open positions

Regional Driving Jobs in Milwaukee

4 open positions

Local Driving Jobs (Home Daily) in Milwaukee

3 open positions

Seasonal Driving Jobs in Milwaukee

2 open positions

Last updated: October 05, 2026