Driving Jobs in Chester, IL — Open Positions

As of April 2026, there are 100+ open driving positions in Chester, IL. Current pay ranges from $500 to $9,520 per year. Top hiring areas include Delivery Driver, General and Weekend. New roles are posted daily — listings on this page are verified and updated regularly.

Final Mile Delivery Co.

Independent Contractor Driver - Final Mile Parcel

Chester, IL

$3,000 - $5,500

Grubhub

Grubhub Large Order Delivery Driver

Chester, IL

$3,500 - $6,000

Shipt

Weekend Shift:Early Morning Shopper-Chester

Chester, GA

$2,200 - $3,800

Uber

Immediate Opening in Chester for a WAV Rideshare Driver | Hiring

Chester, GA

$3,500 - $5,500

Shipt

Student Friendly:Suburban Route Shopper(Chester)

Chester, GA

$2,800 - $4,800

Final Mile Delivery Co.

Independent Contractor Driver - Final Mile Parcel

Chester, GA

$3,000 - $5,500

Grubhub

Campus Area Grubhub Driver

Chester, IL

$2,989 - $5,520

Shipt

Bulk Order Specialist needed in Chester(Apply Now)

Chester, GA

$3,200 - $5,500

Corporate Catering Couriers

Independent Contractor Driver - Catering Logistics

Chester, IL

$3,500 - $6,000

Shipt

(Chester)Part-Time:Driver Opportunity

Chester, GA

$2,500 - $4,500

Shipt

Chester Job:Courier(No Exp Req*)

Chester, IL

$2,000 - $3,500

Uber

Chester Contract:Weekend Ubereats Delivery Professional

Chester, GA

$2,376 - $4,104

Driving Jobs in Chester — FAQ

How many driving jobs are available in Chester, IL right now?
There are currently 100+ open driving positions in Chester, IL. These include delivery drivers, CDL truck drivers, couriers, bus drivers, DSP drivers, and local route positions. New jobs are added daily.
How much do driving jobs pay in Chester?
Driving job pay in Chester varies by role: Delivery drivers earn $18–$25/hr, CDL truck drivers $55K–$90K+/year, couriers $16–$22/hr, and bus drivers $20–$30/hr. Night and weekend routes often pay premium rates.
Can I get a driving job with no experience in Chester?
Yes. Many delivery driver, courier, and DSP positions in Chester require no prior experience and provide paid training. Delivery driver positions require a valid driver's license but no CDL. Some carriers offer free CDL training programs.
What schedules do driving jobs offer in Chester?
Driving jobs in Chester offer flexible schedules: day routes (6 AM–4 PM), evening routes (1 PM–10 PM), overnight/line haul (6 PM–6 AM), and weekend-only schedules (Fri–Sun or Sat–Mon). Part-time and gig-style shifts are also available. Overnight and weekend routes typically pay premium rates.
What benefits do driving jobs offer in Chester?
Benefits vary by employer, but many driving positions in Chester offer: health, dental, and vision insurance; 401(k) or retirement plans; paid time off; sign-on bonuses; weekly or daily pay; company-provided vehicles for delivery positions; and CDL training assistance from select employers.
How much do drivers take home after taxes in Chester?
Your take-home pay as a driver in Chester depends on your pay rate, hours worked, and state tax rate. For example, a delivery driver earning $22/hr in a no-tax state like Texas takes home about $750/week, while in California it's closer to $670/week after state tax.
Are driving companies hiring immediately in Chester?
Yes, many driving positions in Chester are hiring immediately with start dates within 1–2 weeks of applying. Delivery driver and courier roles often offer same-week start dates. Browse the 100+ listings above and apply directly.

Last updated: April 17, 2026