Owner Operators Jobs, Employment in Milwaukee,WI Now Hiring November 2026

CDL A Owner Operator - $1.31 Per Loaded Mile

Forward Air, Inc.

Milwaukee, WI 53244

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.*

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 1 day ago

Recommended

Owner Operators / CDL-A / $1,500 - $2,800 Weekly / 6 Months Exp. Req'd

Bay & Bay Transportation

Milwaukee, WI 53201

$1,500-$2,800/wk

Requires TravelUrgently HiringHealth InsurancePaid Time OffRetirement Benefit

Lease contractors net $1,500 - $1,800 per week

$1.40 - $2.00 CPM plus fuel surcharge

Quarterly bonus program

Detention and layover pay

OTR Owner ops can make between $1800 and $2800 per week

Regional Owner Ops can make between $1500 to $2000 per week

68% line haul and fuel surcharge

Paid by PC Miler practice miles

Company Driver Benefits:$1,300 - $1,800 weekly pay

Drivers start at up to $0.64 CPM

Referral bonus available

2021 - 2024 tractors available

Fully loaded equipment (APU or autostart/stop and inverter in most inventory)

Medical insurance is available through a 3rd party insurance company

Discounts on fuel purchases

Maintenance account for repairs

Daily/weekly direct deposit payroll settlements

Huge fuel discounts

2021 and newer Freightliner and Kenworth T680s

Full medical and dental benefits after 60 days

401(k) - eligible the 1st quarter following 6 months of employment

Orientation attendance pay

Paid holidays, sick time, and vacation

Pet and rider programs available

Regional routes available in the following states and get home weekly: IA, MN, WI, IL, and IN

Drivers are out for 2 - 3 weeks

CDL-A

At least 6 months of OTR tractor-trailer experience

No more than 3 moving violations or three accidents in the last 3 years

New, Posted 16 hours ago

Recommended

Apply Directly

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 16 hours ago

Apply Directly

CDL-A Owner Operator Driver

Forward Air, Inc.

Waukesha, WI 53188

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 just now

Recommended

CDL-A Truck Driver - Owner Operator

TForce Freight

Milwaukee, WI 53204

$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 11 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

Owner Operators / CDL-A / $1,500 - $2,800 Weekly / 6 Months Exp. Req'd

Bay & Bay Transportation

Butler, WI 53007

$1,500-$2,800/wk

Requires TravelUrgently HiringHealth InsurancePaid Time OffRetirement Benefit

Lease contractors net $1,500 - $1,800 per week

$1.40 - $2.00 CPM plus fuel surcharge

Quarterly bonus program

Detention and layover pay

OTR Owner ops can make between $1800 and $2800 per week

Regional Owner Ops can make between $1500 to $2000 per week

68% line haul and fuel surcharge

Paid by PC Miler practice miles

Company Driver Benefits:$1,300 - $1,800 weekly pay

Drivers start at up to $0.64 CPM

Referral bonus available

2021 - 2024 tractors available

Fully loaded equipment (APU or autostart/stop and inverter in most inventory)

Medical insurance is available through a 3rd party insurance company

Discounts on fuel purchases

Maintenance account for repairs

Daily/weekly direct deposit payroll settlements

Huge fuel discounts

2021 and newer Freightliner and Kenworth T680s

Full medical and dental benefits after 60 days

401(k) - eligible the 1st quarter following 6 months of employment

Orientation attendance pay

Paid holidays, sick time, and vacation

Pet and rider programs available

Regional routes available in the following states and get home weekly: IA, MN, WI, IL, and IN

Drivers are out for 2 - 3 weeks

CDL-A

At least 6 months of OTR tractor-trailer experience

No more than 3 moving violations or three accidents in the last 3 years

Recommended

Truck Driver Job Application

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

Hiring Drivers Now

Milwaukee, WI

$200,000-$325,000/yr

Urgently Hiring

New, Posted 1 day ago

Recommended

Owner Operators / CDL-A / $8K - $12K Weekly / 2 Years Exp. Req'd

Amason

Milwaukee, WI 53201

OnsiteUrgently Hiring

$8K - $12K Weekly

Keep 90% of Gross Load Revenue

Estimated Weekly Gross Truck Revenue: $8,000 - $12,000

Referral bonus opportunities

Original rate confirmations directly from the broker?s email

24/7 dispatch support

Dedicated, experienced dispatchers

Self-dispatch

On-site repair shop with 36 bays

Support focused on transparency and owner-operator success

CDL-A

Must possess a valid Class A commercial driver?s license (CDL A)

At least 2 years of verifiable OTR commercial driving experience

Must operate a well-maintained truck that is a 2000-year model or newer

Equipment that meets DOT safety standards

New, Posted 1 day ago

Recommended

CDL-A Truck Driver - Owner Operator - $12,000 Sign-On

Hub Group Trucking

Milwaukee, WI 53215

$161,197-$273,038/yr

$12,000 bonus

OnsiteUrgently Hiring

Average $161,197 - $273,038 Annually, Gross*

$12,000 sign-on bonus for owner operators

100% fuel surcharge

Weekly settlements

Direct deposit

Access to online settlements

Consistent miles - Average up to 2,700 miles per week

Fuel discounts

No-touch freight

Home Most Nights

Home most nights, 2-3 layovers per week

CDL-A

Must have a valid CDL-A License

At least one year of experience

Must be an Owner Operator

1728 Owner Operators jobs in Milwaukee,WI

CDL A Owner Operator - $1.31 Per Loaded Mile

Owner Operators / CDL-A / $1,500 - $2,800 Weekly / 6 Months Exp. Req'd

$1,500-$2,800/wk

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 Truck Drivers - Gross $5k+/Week

$5,000/wk

Owner Operators / CDL-A / $1,500 - $2,800 Weekly / 6 Months Exp. Req'd

$1,500-$2,800/wk

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

$200,000-$325,000/yr

Owner Operators / CDL-A / $8K - $12K Weekly / 2 Years Exp. Req'd

CDL-A Truck Driver - Owner Operator - $12,000 Sign-On

$161,197-$273,038/yr

$12,000 bonus

1728 Owner Operators jobs in Milwaukee,WI

CDL A Owner Operator - $1.31 Per Loaded Mile

Owner Operators / CDL-A / $1,500 - $2,800 Weekly / 6 Months Exp. Req'd

$1,500-$2,800/wk

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 Truck Drivers - Gross $5k+/Week

$5,000/wk

Owner Operators / CDL-A / $1,500 - $2,800 Weekly / 6 Months Exp. Req'd

$1,500-$2,800/wk

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

$200,000-$325,000/yr

Owner Operators / CDL-A / $8K - $12K Weekly / 2 Years Exp. Req'd

CDL-A Truck Driver - Owner Operator - $12,000 Sign-On

$161,197-$273,038/yr

$12,000 bonus

1728 Owner Operators jobs in Milwaukee,WI

CDL A Owner Operator - $1.31 Per Loaded Mile

Owner Operators / CDL-A / $1,500 - $2,800 Weekly / 6 Months Exp. Req'd

$1,500-$2,800/wk

PayLease contractors net $1,500 - $1,800 per weekPay$1.40 - $2.00 CPM plus fuel surchargePayQuarterly bonus program

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 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 Truck Drivers - Gross $5k+/Week

$5,000/wk

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

Owner Operators / CDL-A / $1,500 - $2,800 Weekly / 6 Months Exp. Req'd

$1,500-$2,800/wk

PayLease contractors net $1,500 - $1,800 per weekPay$1.40 - $2.00 CPM plus fuel surchargePayQuarterly bonus program

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

$200,000-$325,000/yr

Owner Operators / CDL-A / $8K - $12K Weekly / 2 Years Exp. Req'd

Pay$8K - $12K WeeklyPayKeep 90% of Gross Load RevenuePayEstimated Weekly Gross Truck Revenue: $8,000 - $12,000

CDL-A Truck Driver - Owner Operator - $12,000 Sign-On

$161,197-$273,038/yr

$12,000 bonus

PayAverage $161,197 - $273,038 Annually, Gross*Pay$12,000 sign-on bonus for owner operatorsPay100% fuel surcharge

1728 Owner Operators jobs in Milwaukee,WI

CDL A Owner Operator - $1.31 Per Loaded Mile

Owner Operators / CDL-A / $1,500 - $2,800 Weekly / 6 Months Exp. Req'd

$1,500-$2,800/wk

PayLease contractors net $1,500 - $1,800 per weekPay$1.40 - $2.00 CPM plus fuel surchargePayQuarterly bonus program

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 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 Truck Drivers - Gross $5k+/Week

$5,000/wk

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

Owner Operators / CDL-A / $1,500 - $2,800 Weekly / 6 Months Exp. Req'd

$1,500-$2,800/wk

PayLease contractors net $1,500 - $1,800 per weekPay$1.40 - $2.00 CPM plus fuel surchargePayQuarterly bonus program

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

$200,000-$325,000/yr

Owner Operators / CDL-A / $8K - $12K Weekly / 2 Years Exp. Req'd

Pay$8K - $12K WeeklyPayKeep 90% of Gross Load RevenuePayEstimated Weekly Gross Truck Revenue: $8,000 - $12,000

CDL-A Truck Driver - Owner Operator - $12,000 Sign-On

$161,197-$273,038/yr

$12,000 bonus

PayAverage $161,197 - $273,038 Annually, Gross*Pay$12,000 sign-on bonus for owner operatorsPay100% fuel surcharge