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Assistant Owner Driver Jobs in Chicago, IL (NOW HIRING)

Norbet Trucking

Owner Operator EC

East Chicago, IN · On-site

Hiring an experienced CDL-A Owner Operatorssteady loads, competitive rates, and a company you can ... transport. Assist in loading and unloading as required. Layover is possible for 1 or 2 nights ...

Logix Transportation

CDL A Owner Operator

Gary, IN · On-site

$234K - $286K/yr

Owner Operators... Pay yourself FIRST with lightweight freight! Logix isn't your typical hauler ... Driver assist in each load * Reasonable delivery spreads Ask us about our industry leading lease ...

Logix Transportation

CDL A Owner Operator

Joliet, IL · On-site

$234K - $286K/yr

Owner Operators... Pay yourself FIRST with lightweight freight! Logix isn't your typical hauler ... Driver assist in each load * Reasonable delivery spreads Ask us about our industry leading lease ...

CRST

CDL A Owner Operator Truck Driver

Chicago, IL · On-site

$8.0K - $10K/wk

CRST Specialized Solutions is looking for independent contractor teams (Owner Operators) to haul ... Driver assist position - loading and unloading freight Compensation & Benefits: * Tolls are 100 ...

CRST

CDL A Owner Operator Truck Driver

Chicago, IL · On-site

$8.0K - $10K/wk

CRST Specialized Solutions is looking for independent contractor teams (Owner Operators) to haul ... Driver assist position - loading and unloading freight Compensation & Benefits: * Tolls are 100 ...

Webb Chevrolet Plainfield

Parts Driver

Plainfield, IL

$17/hr

About Us Webb Automotive is a family-owned and operated dealership group serving the Chicagoland ... Support stock replenishment and assist with bin counts for inventory management * Adhere to all ...

CRST

CDL A Owner Operator Truck Driver

Plainfield, IL · On-site

$8.0K - $10K/wk

CRST Specialized Solutions is looking for independent contractor teams (Owner Operators) to haul ... Driver assist position - loading and unloading freight Compensation & Benefits: * Tolls are 100 ...

CRST

CDL A Owner Operator Truck Driver

Chicago, IL · On-site

$8.0K - $10K/wk

CRST Specialized Solutions is looking for independent contractor teams (Owner Operators) to haul ... Driver assist position - loading and unloading freight Compensation & Benefits: * Tolls are 100 ...

CRST

CDL A Owner Operator Truck Driver

Chicago, IL · On-site

$8.0K - $10K/wk

CRST Specialized Solutions is looking for independent contractor teams (Owner Operators) to haul ... Driver assist position - loading and unloading freight Compensation & Benefits: * Tolls are 100 ...

CRST

CDL A Owner Operator Truck Driver

West Chicago, IL · On-site

$8.0K - $10K/wk

CRST Specialized Solutions is looking for independent contractor teams (Owner Operators) to haul ... Driver assist position - loading and unloading freight Compensation & Benefits: * Tolls are 100 ...

CRST

CDL A Owner Operator Truck Driver

Naperville, IL · On-site

$8.0K - $10K/wk

CRST Specialized Solutions is looking for independent contractor teams (Owner Operators) to haul ... Driver assist position - loading and unloading freight Compensation & Benefits: * Tolls are 100 ...

CRST

CDL A Owner Operator Truck Driver

Lockport, IL · On-site

$8.0K - $10K/wk

CRST Specialized Solutions is looking for independent contractor teams (Owner Operators) to haul ... Driver assist position - loading and unloading freight Compensation & Benefits: * Tolls are 100 ...

CRST

CDL A Owner Operator Truck Driver

Chicago, IL · On-site

$8.0K - $10K/wk

CRST Specialized Solutions is looking for independent contractor teams (Owner Operators) to haul ... Driver assist position - loading and unloading freight Compensation & Benefits: * Tolls are 100 ...

CRST

CDL A Owner Operator Truck Driver

Berwyn, IL · On-site

$8.0K - $10K/wk

CRST Specialized Solutions is looking for independent contractor teams (Owner Operators) to haul ... Driver assist position - loading and unloading freight Compensation & Benefits: * Tolls are 100 ...

CRST

CDL A Owner Operator Truck Driver

Chicago, IL · On-site

$8.0K - $10K/wk

CRST Specialized Solutions is looking for independent contractor teams (Owner Operators) to haul ... Driver assist position - loading and unloading freight Compensation & Benefits: * Tolls are 100 ...

CRST

CDL A Owner Operator Truck Driver

Oak Lawn, IL · On-site

$8.0K - $10K/wk

CRST Specialized Solutions is looking for independent contractor teams (Owner Operators) to haul ... Driver assist position - loading and unloading freight Compensation & Benefits: * Tolls are 100 ...

CRST

CDL A Owner Operator Truck Driver

Chicago, IL · On-site

$8.0K - $10K/wk

CRST Specialized Solutions is looking for independent contractor teams (Owner Operators) to haul ... Driver assist position - loading and unloading freight Compensation & Benefits: * Tolls are 100 ...

CRST

CDL A Owner Operator Truck Driver

Chicago, IL · On-site

$8.0K - $10K/wk

CRST Specialized Solutions is looking for independent contractor teams (Owner Operators) to haul ... Driver assist position - loading and unloading freight Compensation & Benefits: * Tolls are 100 ...

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Showing results 21-40

All JobsOwner Driver JobsAssistant Owner Driver JobsAssistant Owner Driver Jobs in Chicago, IL

Assistant Owner Driver information

See Chicago, IL salary details

$9

$17

$24

How much do assistant owner driver jobs pay per hour?

As of Sep 6, 2026, the average hourly pay for assistant owner driver in Chicago, IL is $17.45, according to ZipRecruiter salary data. Most workers in this role earn between $15.58 and $18.80 per hour, depending on experience, location, and employer.

What are the most commonly searched types of Owner Driver jobs in Chicago, IL?

The most popular types of Owner Driver jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Assistant Owner Driver jobs?

Cities near Chicago, IL with the most Assistant Owner Driver job openings:

Assistant Owner Driver jobs near you

Local CDL A Owner Operator Driver - Home Daily

Roadrunner

Arlington Heights, IL • On-site

$500 - $800/day

Other

Medical, Dental

Re-posted 7 days ago

Roadrunner Freight rating

5.6

Company rating: 5.6 out of 10

Based on 13 frontline employees who took The Breakroom Quiz

Job description

Contracting CDL-A Truck Drivers
  • HIGH PAY. REAL FREEDOM - Up to $40 per hour*
  • RUN YOUR BUSINESS YOUR WAY - No forced dispatch, no company drivers
  • YOUR ROUTE, YOUR WAY - Get home daily with a M-F schedule
Run with the Best

Roadrunner is built differently-because it's built for Owner Operators. There are no company drivers, no competing for freight, and no forced dispatch. You choose your loads, routes, and home time while running under a model designed for independence.

With consistent freight, stable rates, and full back-end support, Roadrunner gives you the tools to grow your business-without the usual headaches of running it alone.

Contracting Local Owner Operators
  • Strong daily earnings. Earn $24-$40/hour + accessorials, averaging $500-$800/day for day cabs and $300-$500/day for box trucks.*
  • Home daily schedule. Run Monday-Friday routes with optional weekend work and start times between 7-10 AM.
  • Consistent local routes. Average 200-250 miles per day on pre-planned deliveries.
  • Hands-on local work. Driver assist required for load/unload; box trucks must have pallet jacks and lift gates.
Benefits & Perks
  • 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.
  • Rare health coverage benefits. We offer affordable medical and dental insurance plans, so you're not sacrificing your health for your business.
  • Referral bonuses that pay big. Earn $1,000 for solos and $4,000 for teams.
  • Driver-friendly policies. Pet and rider programs available.

All pay and bonus amounts may vary by job type, location, experience level, and performance and are subject to change based on company discretion. Drivers required to have inward facing cameras. Talk with a recruiter to confirm specific details.

There is no deadline to apply. Applications are accepted on an ongoing basis.

Driver Requirements
  • 18 months of verifiable driving experience
  • Must own their own equipment

What Roadrunner Freight employees say

Pay

Benefits

Hours and flexibility

Workplace

Get the full story on Breakroom

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