Owner Operator & Lease Purchase in Chicago, IL — Immediate Openings

As of September 2026, there are 7 owner operator & lease purchase openings in Chicago, IL. Local pay ranges from $1,760 to $130,000/year. Listings are updated daily — many roles offer flexible hours and employee discounts.

Atlas Van Lines

Driver Opportunity needed in Chicago(Apply Now)

Chicago, IL

$89,250 - $115,500

Hot Shot Transportation Co.

Flexible Gig:Hot Shot Truck Driver-Owner Operator With 1 Ton Pickup

Chicago, IL

$85,000 - $130,000

Auto Logistics Pros

Independent Contractor Driver - Auto Parts Courier

Chicago, IL

$2,464 - $4,224

Corporate Catering Couriers

Independent Contractor Driver - Catering Logistics

Chicago, IL

$3,500 - $6,000

On-Demand Tasks Network

Independent Contractor Driver - On-Demand Errands (TaskRabbit/Roadie)

Chicago, IL

$1,760 - $3,520

Urban Pedal Logistics

Independent Contractor Driver - Urban E-Bike/Scooter Courier

Chicago, IL

$2,500 - $4,500

Regional Expedite Logistics

Independent Contractor Driver - Long Distance / Regional Courier

Chicago, IL

$3,675 - $6,300

Owner Operator & Lease Purchase in Chicago — FAQ

How many owner operator & lease purchase jobs are open in Chicago, IL?
There are currently 7+ owner operator & lease purchase in Chicago, IL. New owner operator & lease purchase roles are added regularly — check this page for the latest openings.
How much do owner operator & lease purchase jobs pay in Chicago?
Pay for owner operator & lease purchase in Chicago 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 owner operator & lease purchase positions require experience in Chicago?
Many owner operator & lease purchase positions in Chicago require no prior experience, and most employers provide paid on-the-job training. Check individual listings for specific requirements.
How do I apply for owner operator & lease purchase jobs in Chicago?
Browse the 7+ owner operator & lease purchase 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.

Owner Operator & Lease Purchase in Other Cities

Owner Operator & Lease Purchase in New York

7 open positions

Owner Operator & Lease Purchase in Los Angeles

14 open positions

Owner Operator & Lease Purchase in Houston

7 open positions

Owner Operator & Lease Purchase in Phoenix

7 open positions

Owner Operator & Lease Purchase in Philadelphia

7 open positions

Owner Operator & Lease Purchase in San Antonio

7 open positions

Owner Operator & Lease Purchase in San Diego

7 open positions

Owner Operator & Lease Purchase in Dallas

7 open positions

Owner Operator & Lease Purchase in Fort Worth

7 open positions

Owner Operator & Lease Purchase in Austin

7 open positions

Other Driving Careers in Chicago

Full-Time Driving Jobs in Chicago

181 open positions

Delivery Driver Jobs in Chicago

175 open positions

CDL-B Driving Jobs in Chicago

90 open positions

Non-CDL Driving Jobs in Chicago

68 open positions

Weekend Driving Jobs in Chicago

57 open positions

CDL-A Truck Driving Jobs in Chicago

31 open positions

Local Driving Jobs (Home Daily) in Chicago

25 open positions

Part-Time Driving Jobs in Chicago

21 open positions

Last updated: September 29, 2026