Owner Operators Jobs, Employment in Wisconsin Now Hiring November 2026

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CDL-A Owner Operator Truck Driver Jobs ($200k - $325k+ a Yr!) Apply Now!

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all cities, WI

$200,000-$325,000/yr

Urgently Hiring

New, Posted 22 hours ago

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Local CDL A Owner Operator Driver - Home Daily

roadrunner

Milwaukee, WI 53244

$40/hr

OnsiteUrgently Hiring

Up to $40 per hour*

Earn $24-$40/hour + accessorials, averaging $500-$800/day for day cabs and $300-$500/day for box trucks.*

Earn $1,000 for solos and $4,000 for teams.

Run under Roadrunner's DOT for free.

We offer affordable medical and dental insurance plans

Pet and rider programs available.

Home daily

Get home daily with a M-F schedule

Run Monday-Friday routes with optional weekend work and start times between 7-10 AM.

Optional weekend work

CDL A

12+ months of verifiable driving experience

Must own their own equipment

Drivers required to have inward facing cameras

Box trucks must have pallet jacks and lift gates

New, Posted 21 hours ago

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CDL-A Owner Operator Driver

Forward Air, Inc.

Milton, WI 53563

Requires TravelUrgently Hiring

Earn up to $250,000 gross per year*

Solo Owner Operators earn up to $250,000 gross per year*, with base compensation of $1.31 per loaded mile and $1.18 per empty mile plus FSC*, averaging $4,100 to $5,200 gross per week*, plus additional compensation on all miles based on load destination.

$5,000 paid out within your first year.*

A substantial fuel surcharge program

Drivers are typically out on the road 2 to 3 weeks at a time.

CDL-A

Valid Class A CDL

12+ months verifiable driving experience

Must be 23 years of age

Equipment must be newer than 10 years old

New, Posted 19 hours ago

Recommended

CDL-A Truck Driver - Owner Operator

TForce Freight

La Crosse, WI 54601

$4,500-$5,000/wk

OnsiteUrgently Hiring

Solos Average $225,000 - $250,000 per Year, Gross

Teams Average $475,000 - $500,000 per Year, Gross

Average $225,000 - $250,000 per year, gross

Average $4,500 - $5,000 per week, gross

Average $475,000 - $500,000 per year, gross

Average $9,500 - $10,000 per week, gross

Detention, layover, and stop pay.

Referral bonus: $500 for solo, $1,000 for teams

Empty miles paid at 80% of loaded rate

Fuel discounts: up to $1 off on all fuel

No trailer fees

Excellent tire discounts offered

Tolls and scales paid – PrePass Elite provided

Typically out 8-10 days

CDL-A

Class A CDL

Minimum 1 year of over-the-road experience

Must own your own truck

Doubles and hazmat endorsements offers top rate pay

New, Posted 21 hours ago

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CDL-A Owner Operator Driver

Forward Air, Inc.

Madison, WI 53774

Requires TravelUrgently Hiring

Earn up to $250,000 gross per year*

Solo Owner Operators earn up to $250,000 gross per year*, with base compensation of $1.31 per loaded mile and $1.18 per empty mile plus FSC*, averaging $4,100 to $5,200 gross per week*, plus additional compensation on all miles based on load destination.

$5,000 paid out within your first year.*

A substantial fuel surcharge program

Drivers are typically out on the road 2 to 3 weeks at a time.

CDL-A

Valid Class A CDL

12+ months verifiable driving experience

Must be 23 years of age

Equipment must be newer than 10 years old

New, Posted 13 hours ago

Recommended

Team Owner Operators / CDL-A / $300K - $350K Yearly

Clark Transfer

Odanah, WI 54861

$3,500/wk

OnsiteUrgently HiringHealth Insurance

Most singles earn $200,000 to $250,000+ on less than 85k miles

Most teams earn $300,000-$350,000+ on less than 110k miles

Solos: Guaranteed minimum weekly average: $3,500/week worked (most earn $3,750 - $4,250+)

Teams: Guaranteed minimum weekly average: $5,000/week worked (most earn $5,500 - $6,500+)

Startup Weekly Guarantee: $3,500/$5,000 paid weekly for your first four weeks, including orientation

Quarterly bonus of $2,500/$5,000 per quarter for Singles/Teams

$1.60/gallon or lower fuel price guarantee (average after fuel surcharge)

Up to $5,000 referral bonus

All miles paid, plus fuel surcharge

Detention pay

Company supported owner-operator health insurance program

Paid fuel permits & fuel taxes

Paid tolls while under dispatch via company provided transponder

Paid cargo/liability insurance

Year-round work

Tours may require up to 6 weeks away from home

CDL-A

Must be an owner-operator

At least 23 years of age or older

At least 2 years of verifiable OTR experience

Clean motor vehicle record for the last 3 years

No more than 6 jobs in last 3 years

Passport and ability to enter Canada

2021 or newer tractor

Tours may require up to 6 weeks away from home

New, Posted 21 hours ago

Recommended

Apply Directly

Local CDL A Owner Operator Driver - Home Daily

roadrunner

Kenosha, WI 53142

$40/hr

OnsiteUrgently Hiring

Up to $40 per hour*

Earn $24-$40/hour + accessorials, averaging $500-$800/day for day cabs and $300-$500/day for box trucks.*

Earn $1,000 for solos and $4,000 for teams.

Run under Roadrunner's DOT for free.

We offer affordable medical and dental insurance plans

Pet and rider programs available.

Home daily

Get home daily with a M-F schedule

Run Monday-Friday routes with optional weekend work and start times between 7-10 AM.

Optional weekend work

CDL A

12+ months of verifiable driving experience

Must own their own equipment

Drivers required to have inward facing cameras

Box trucks must have pallet jacks and lift gates

New, Posted 19 hours ago

Recommended

CDL-A Owner Operator Truck Drivers - Gross $5k+/Week

USA Truck

Milwaukee, WI 53215

$5,000/wk

OnsiteUrgently Hiring

Gross $5k+/Week

Earn $5,000+ Gross Weekly

Scalable Pay-Out Rate

1st load pays out to the OO at 70% of the all-in rate

2nd load pays out to the OO at 70% of the all-in rate

3rd load pays out to the OO at 75% of the all-in rate

4th load (plus any additional load during that week) pays out to the OO at 80% of the all-in rate

100% of the fuel discount

100% of the fuel discount with multiple major vendors

Independent Contractor Fuel Match Program available

Up to $1.25 per gallon

70% of the fuel surcharge

Referral bonus

No weekly payment for your first 8 weeks

That's $6,000 in savings!

$1,000 Origination Fee (not toward the truck lease) paid $250 for four weeks

$400 Maintenance Escrow deposits during promo

Free E-ZPass

Paid orientation

Down payment assistance available if needed

CDL-A

Valid CDL-A

Must be at least 21 years of age

12+ months CDL-A driving experience required

No DUI, DWI, or moving violations involving drugs or alcohol in the last 3 years

New, Posted 1 day ago

Recommended

Apply Directly

CDL-A Owner Operator

Kenan Advantage Group

Hager City, WI 54014

$350,000/yr

Requires Travel

$300,000 – $350,000+ Annual Gross Revenue ($6,000 - $7,000+ Weekly)

$1.70–$1.77 per dispatched mile

PLUS Fuel Surcharge

2,500–3,000 dispatched miles every week

10–14 day OTR schedules

CDL-A

Minimum 12 months of recent, verifiable tractor-trailer experience

Tanker endorsement & TWIC required

Non-Trucking (Bobtail) Insurance

Tractor must be 10 years old or newer

Passport preferred

New, Posted 19 hours ago

Recommended

CDL-A Truck Driver - Owner Operator

TForce Freight

Beloit, WI 53511

$4,500-$5,000/wk

OnsiteUrgently Hiring

Solos Average $225,000 - $250,000 per Year, Gross

Teams Average $475,000 - $500,000 per Year, Gross

Average $225,000 - $250,000 per year, gross

Average $4,500 - $5,000 per week, gross

Average $475,000 - $500,000 per year, gross

Average $9,500 - $10,000 per week, gross

Detention, layover, and stop pay.

Referral bonus: $500 for solo, $1,000 for teams

Empty miles paid at 80% of loaded rate

Fuel discounts: up to $1 off on all fuel

No trailer fees

Excellent tire discounts offered

Tolls and scales paid – PrePass Elite provided

Typically out 8-10 days

CDL-A

Class A CDL

Minimum 1 year of over-the-road experience

Must own your own truck

Doubles and hazmat endorsements offers top rate pay

978 Owner Operators jobs in Wisconsin

CDL-A Owner Operator Truck Driver Jobs ($200k - $325k+ a Yr!) Apply Now!

$200,000-$325,000/yr

Local CDL A Owner Operator Driver - Home Daily

$40/hr

CDL-A Owner Operator Driver

CDL-A Truck Driver - Owner Operator

$4,500-$5,000/wk

CDL-A Owner Operator Driver

Team Owner Operators / CDL-A / $300K - $350K Yearly

$3,500/wk

Local CDL A Owner Operator Driver - Home Daily

$40/hr

CDL-A Owner Operator Truck Drivers - Gross $5k+/Week

$5,000/wk

CDL-A Owner Operator

$350,000/yr

CDL-A Truck Driver - Owner Operator

$4,500-$5,000/wk

978 Owner Operators jobs in Wisconsin

CDL-A Owner Operator Truck Driver Jobs ($200k - $325k+ a Yr!) Apply Now!

$200,000-$325,000/yr

Local CDL A Owner Operator Driver - Home Daily

$40/hr

CDL-A Owner Operator Driver

CDL-A Truck Driver - Owner Operator

$4,500-$5,000/wk

CDL-A Owner Operator Driver

Team Owner Operators / CDL-A / $300K - $350K Yearly

$3,500/wk

Local CDL A Owner Operator Driver - Home Daily

$40/hr

CDL-A Owner Operator Truck Drivers - Gross $5k+/Week

$5,000/wk

CDL-A Owner Operator

$350,000/yr

CDL-A Truck Driver - Owner Operator

$4,500-$5,000/wk

978 Owner Operators jobs in Wisconsin

CDL-A Owner Operator Truck Driver Jobs ($200k - $325k+ a Yr!) Apply Now!

$200,000-$325,000/yr

Local CDL A Owner Operator Driver - Home Daily

$40/hr

CDL-A Owner Operator Driver

PayEarn up to $250,000 gross per year*Pay$5,000 paid out within your first year.*PayA substantial fuel surcharge program

CDL-A Truck Driver - Owner Operator

$4,500-$5,000/wk

PaySolos Average $225,000 - $250,000 per Year, GrossPayTeams Average $475,000 - $500,000 per Year, GrossPayAverage $225,000 - $250,000 per year, gross

CDL-A Owner Operator Driver

PayEarn up to $250,000 gross per year*Pay$5,000 paid out within your first year.*PayA substantial fuel surcharge program

Team Owner Operators / CDL-A / $300K - $350K Yearly

$3,500/wk

PayMost singles earn $200,000 to $250,000+ on less than 85k milesPayMost teams earn $300,000-$350,000+ on less than 110k milesPayQuarterly bonus of $2,500/$5,000 per quarter for Singles/Teams

Local CDL A Owner Operator Driver - Home Daily

$40/hr

PayUp to $40 per hour*PayEarn $1,000 for solos and $4,000 for teamsPayEarn $24-$40/hour + accessorials, averaging $500-$800/day for day cabs and $300-$500/day for box trucks.*

CDL-A Owner Operator Truck Drivers - Gross $5k+/Week

$5,000/wk

PayGross $5k+/WeekPayEarn $5,000+ Gross WeeklyPayScalable Pay-Out Rate

CDL-A Owner Operator

$350,000/yr

Pay$1.70–$1.77 per dispatched milePayPLUS Fuel SurchargePay$300,000 – $350,000+ Annual Gross Revenue ($6,000 - $7,000+ Weekly)

CDL-A Truck Driver - Owner Operator

$4,500-$5,000/wk

PaySolos Average $225,000 - $250,000 per Year, GrossPayTeams Average $475,000 - $500,000 per Year, GrossPayAverage $225,000 - $250,000 per year, gross

978 Owner Operators jobs in Wisconsin

CDL-A Owner Operator Truck Driver Jobs ($200k - $325k+ a Yr!) Apply Now!

$200,000-$325,000/yr

Local CDL A Owner Operator Driver - Home Daily

$40/hr

CDL-A Owner Operator Driver

PayEarn up to $250,000 gross per year*Pay$5,000 paid out within your first year.*PayA substantial fuel surcharge program

CDL-A Truck Driver - Owner Operator

$4,500-$5,000/wk

PaySolos Average $225,000 - $250,000 per Year, GrossPayTeams Average $475,000 - $500,000 per Year, GrossPayAverage $225,000 - $250,000 per year, gross

CDL-A Owner Operator Driver

PayEarn up to $250,000 gross per year*Pay$5,000 paid out within your first year.*PayA substantial fuel surcharge program

Team Owner Operators / CDL-A / $300K - $350K Yearly

$3,500/wk

PayMost singles earn $200,000 to $250,000+ on less than 85k milesPayMost teams earn $300,000-$350,000+ on less than 110k milesPayQuarterly bonus of $2,500/$5,000 per quarter for Singles/Teams

Local CDL A Owner Operator Driver - Home Daily

$40/hr

PayUp to $40 per hour*PayEarn $1,000 for solos and $4,000 for teamsPayEarn $24-$40/hour + accessorials, averaging $500-$800/day for day cabs and $300-$500/day for box trucks.*

CDL-A Owner Operator Truck Drivers - Gross $5k+/Week

$5,000/wk

PayGross $5k+/WeekPayEarn $5,000+ Gross WeeklyPayScalable Pay-Out Rate

CDL-A Owner Operator

$350,000/yr

Pay$1.70–$1.77 per dispatched milePayPLUS Fuel SurchargePay$300,000 – $350,000+ Annual Gross Revenue ($6,000 - $7,000+ Weekly)

CDL-A Truck Driver - Owner Operator

$4,500-$5,000/wk

PaySolos Average $225,000 - $250,000 per Year, GrossPayTeams Average $475,000 - $500,000 per Year, GrossPayAverage $225,000 - $250,000 per year, gross