Driving Jobs in Chicago, IL — Apply Today

As of May 2026, there are 180+ open driving positions in Chicago, IL. Current pay ranges from $455 to $10,000 per year. Top hiring areas include Delivery Driver, General and Part Time. New roles are posted daily — listings on this page are verified and updated regularly.

Secure Document Couriers

Independent Contractor Driver - Night Shift Legal/Document Courier

Chicago, IL

$2,800 - $5,000

Final Mile Delivery Co.

Final Mile Delivery Co. Needs Independent Contractor Driver-Final Mile

Chicago, IL

$3,000 - $5,500

Grubhub

Night Shift Grubhub Courier

Chicago, IL

$2,576 - $4,416

Local Logistics Network

Apply Now:Independent Contractor Driver-Medical Courier in Chicago,IL

Chicago, IL

$2,640 - $4,400

DoorDash

Part-Time DoorDash Driver (Lunch Rush Specialist)

Chicago, IL

$800 - $1,800

Urban Pedal Logistics

$2.3k-$4.1k/Month Independent Contractor Driver-Urban E-bike/scooter

Chicago, IL

$2,300 - $4,140

Lyft

Immediate Opening in Chicago for a Part-time Rideshare Driver

Chicago, IL

$500 - $1,500

Instacart

Suburban Instacart Shopper

Chicago, IL

$2,940 - $5,040

Instacart

Early Morning Instacart Shopper

Chicago, IL

$2,310 - $3,990

FedEx Ground Independent Service Provider

Fedex Ground Route Delivery Driver(Contract)|Chicago

Chicago, IL

$3,500 - $5,500

Uber

Chicago-based Part-time Driver Opening | Hiring

Chicago, IL

$455 - $1,365

Uber

Work in Chicago:Weekend Driver | Hiring

Chicago, IL

$2,240 - $3,920

Driving Jobs in Chicago — FAQ

How many driving jobs are available in Chicago, IL right now?
There are currently 180+ open driving positions in Chicago, 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 Chicago?
Driving job pay in Chicago 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 Chicago?
Yes. Many delivery driver, courier, and DSP positions in Chicago 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 Chicago?
Driving jobs in Chicago 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 Chicago?
Benefits vary by employer, but many driving positions in Chicago 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 Chicago?
Your take-home pay as a driver in Chicago 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 Chicago?
Yes, many driving positions in Chicago 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 180+ listings above and apply directly.

Last updated: May 04, 2026