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

As of October 2026, there are 9 owner operator & lease purchase openings in Chicago, IL. Local pay ranges from $2,300 to $143,000/year. Listings are updated daily — many roles offer flexible hours and employee discounts.

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

$3,185 - $5,460

Secure Document Couriers

Independent Contractor Driver - Night Shift Legal/Document Courier

Chicago, IL

$2,800 - $5,000

Auto Logistics Pros

Independent Contractor Driver - Auto Parts Courier

Chicago, IL

$2,576 - $4,416

Corporate Catering Couriers

Independent Contractor Driver - Catering Logistics

Chicago, IL

$3,675 - $6,300

Local Merchant Delivery Network

Independent Contractor Driver - Early Morning Bakery/Floral

Chicago, IL

$2,688 - $4,704

Final Mile Delivery Co.

Independent Contractor Driver - Final Mile Parcel

Chicago, IL

$2,730 - $5,005

On-Demand Tasks Network

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

Chicago, IL

$2,300 - $4,600

Hot Shot Transportation Co.

Hot Shot Truck Driver - Owner Operator with 1 Ton Pickup

Chicago, IL

$93,500 - $143,000

Owner Operator & Lease Purchase in Chicago — FAQ

How many owner operator & lease purchase jobs are open in Chicago, IL?
There are currently 9+ 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 9+ 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

9 open positions

Owner Operator & Lease Purchase in Los Angeles

18 open positions

Owner Operator & Lease Purchase in Houston

9 open positions

Owner Operator & Lease Purchase in Phoenix

9 open positions

Owner Operator & Lease Purchase in Philadelphia

9 open positions

Owner Operator & Lease Purchase in San Antonio

9 open positions

Owner Operator & Lease Purchase in San Diego

9 open positions

Owner Operator & Lease Purchase in Dallas

9 open positions

Owner Operator & Lease Purchase in Fort Worth

9 open positions

Owner Operator & Lease Purchase in Austin

9 open positions

Other Driving Careers in Chicago

Full-Time Driving Jobs in Chicago

163 open positions

Delivery Driver Jobs in Chicago

157 open positions

CDL-B Driving Jobs in Chicago

55 open positions

CDL-A Truck Driving Jobs in Chicago

53 open positions

Part-Time Driving Jobs in Chicago

27 open positions

Local Driving Jobs (Home Daily) in Chicago

19 open positions

Flatbed Driving Jobs in Chicago

16 open positions

Weekend Driving Jobs in Chicago

8 open positions

Last updated: October 28, 2026