Regional Driving Jobs in Chicago, IL — Now Hiring

As of October 2026, there are 7 regional driving openings in Chicago, IL. Local pay ranges from $3,000 to $143,000/year. Listings are updated daily — many roles offer flexible hours and employee discounts.

Regional Expedite Logistics

Independent Contractor Driver - Long Distance / Regional Courier

Chicago, IL

$3,185 - $5,460

Regional Expedite Logistics

Driver Opportunity needed in Chicago(Apply Now)

Chicago, IL

$3,500 - $6,000

Nightline Freight

Start ASAP:Driver Opportunity(Chicago)

Chicago, IL

$3,420 - $4,940

Carquest Auto Parts

Chicago Full-time Carquest Regional Parts Transfer Driver | Hiring

Chicago, IL

$3,400 - $5,000

Regional Auto Dealership Group

OEM Dealership Auto Parts Delivery Driver(Automotive

Chicago, IL

$3,000 - $4,500

Hot Shot Transportation Co.

Hot Shot Truck Driver - Owner Operator with 1 Ton Pickup

Chicago, IL

$93,500 - $143,000

Foremost Transport

Mobile Home Transport Driver - CDL A Oversize Load

Chicago, IL

$90,000 - $120,000

Regional Driving Jobs in Chicago — FAQ

How many regional driving jobs are open in Chicago, IL?
There are currently 7+ regional driving in Chicago, IL. New regional driving roles are added regularly — check this page for the latest openings.
How much do regional driving jobs pay in Chicago?
Pay for regional driving 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 regional driving positions require experience in Chicago?
Many regional driving 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 regional driving jobs in Chicago?
Browse the 7+ regional driving 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.

Regional Driving Jobs in Other Cities

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7 open positions

Regional Driving Jobs in Los Angeles

14 open positions

Regional Driving Jobs in Houston

7 open positions

Regional Driving Jobs in Phoenix

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Regional Driving Jobs in Philadelphia

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Regional Driving Jobs in San Antonio

7 open positions

Regional Driving Jobs in San Diego

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Regional Driving Jobs in Dallas

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Regional Driving Jobs in Fort Worth

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Regional Driving Jobs in Austin

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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

Owner Operator & Lease Purchase in Chicago

9 open positions

Last updated: October 28, 2026