Owner Operators Jobs, Employment in Chicago,IL Now Hiring November 2026

Local CDL A Owner Operator Driver - Home Daily

roadrunner

Chicago, IL 60290

$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 17 hours ago

Recommended

Apply Directly

CDL-A Owner Operator Driver

Forward Air, Inc.

Chicago, IL 60290

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 17 hours ago

Recommended

Apply Directly

CDL-A Owner Operator Driver - Local, Home Daily Routes

roadrunner

Arlington Heights, IL 60005

$40/hr

~ 36 min 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.

Let us handle the admin workload, lower your truck insurance and plate costs, and support your business while you focus on the road.

We offer affordable medical and dental insurance plans, so you're not sacrificing your health for your business.

Pet and rider programs available.

Get home daily with a M-F schedule

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

CDL-A

12+ months of verifiable driving experience

Must own their own equipment

Box trucks must have pallet jacks and lift gates

Drivers required to have inward facing cameras.

New, Posted 1 day ago

Recommended

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

Bay & Bay Transportation

Berwyn, IL 60402

$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 1 day ago

Recommended

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

Amason

Chicago, IL 60290

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

Cicero, IL 60804

$161,197-$273,038/yr

$12,000 bonus

~ 16 min 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

New, Posted 17 hours ago

Apply Directly

CDL-A Owner Operator Driver

Forward Air, Inc.

Lisle, IL 60532

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 1 day ago

Recommended

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

Amason

Cicero, IL 60804

~ 16 min 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

Recommended

Truck Driver Job Application

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

Hiring Drivers Now

Chicago, IL

$200,000-$325,000/yr

Urgently Hiring

New, Posted 17 hours ago

Owner Operators / CDL-A / Avg. Weekly Gross $4,300 - $6,000 / 1 Year EXP Req'd

BLAIR

Cicero, IL 60804

$5,000 bonus

Requires TravelUrgently HiringFlexible Schedule

Avg. Weekly Gross $4,300 - $6,000

Average Weekly Take Home: $1,600-$3,000

Average weekly gross: $4,300-$6,000

Average weekly take home: $1,600-$3,000

$5,000 sign-on bonus

Receive $2,500 after your 1st load

$5,000 referral bonus

Receive $2,000 after your 1st load

$4,300-$6,000

$1,600-$3,000

$3,000 referral bonus

Receive $1,500 after your 1st load

High earnings potential: Earn up to 76% of linehaul revenue

Better pay for bigger operations. Higher percentages for multiple trucks and trailers

Warranty Program Available!

No money down & no credit check

100% of trailer maintenance covered by Blair when pulling Blair's trailer

Warranty program available!

Low weekly payment

Contractors get 100% of the Fuel discounts at the pump

Maintenance, equipment & tire discounts

Must have a valid Class A CDL

Must be at least 22 years old

Must have 1 year of OTR experience in the last 5 years

Must have 6 months of flatbed experience in the last 10 years

No felonies within the last 10 years

Owner Operators can never have failed or refused to submit to a pre-employment or random drug or alcohol test with any employer

2334 Owner Operators jobs in Chicago,IL

Local CDL A Owner Operator Driver - Home Daily

$40/hr

CDL-A Owner Operator Driver

CDL-A Owner Operator Driver - Local, Home Daily Routes

$40/hr

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

$1,500-$2,800/wk

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

CDL-A Owner Operator Driver

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

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

$200,000-$325,000/yr

Owner Operators / CDL-A / Avg. Weekly Gross $4,300 - $6,000 / 1 Year EXP Req'd

$5,000 bonus

2334 Owner Operators jobs in Chicago,IL

Local CDL A Owner Operator Driver - Home Daily

$40/hr

CDL-A Owner Operator Driver

CDL-A Owner Operator Driver - Local, Home Daily Routes

$40/hr

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

$1,500-$2,800/wk

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

CDL-A Owner Operator Driver

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

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

$200,000-$325,000/yr

Owner Operators / CDL-A / Avg. Weekly Gross $4,300 - $6,000 / 1 Year EXP Req'd

$5,000 bonus

2334 Owner Operators jobs in Chicago,IL

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 Owner Operator Driver - Local, Home Daily Routes

$40/hr

PayUp to $40 per hourPayEarn $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

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

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

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

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

$200,000-$325,000/yr

Owner Operators / CDL-A / Avg. Weekly Gross $4,300 - $6,000 / 1 Year EXP Req'd

$5,000 bonus

PayAvg. Weekly Gross $4,300 - $6,000PayAverage Weekly Take Home: $1,600-$3,000PayAverage weekly gross: $4,300-$6,000

2334 Owner Operators jobs in Chicago,IL

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 Owner Operator Driver - Local, Home Daily Routes

$40/hr

PayUp to $40 per hourPayEarn $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

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

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

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

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

$200,000-$325,000/yr

Owner Operators / CDL-A / Avg. Weekly Gross $4,300 - $6,000 / 1 Year EXP Req'd

$5,000 bonus

PayAvg. Weekly Gross $4,300 - $6,000PayAverage Weekly Take Home: $1,600-$3,000PayAverage weekly gross: $4,300-$6,000