Driving Jobs in Chicago, IL — Apply Today

As of April 2026, there are 140+ open driving positions in Chicago, IL. Current pay ranges from $455 to $9,350 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.

Shipt

Start ASAP:Evening & Night Shift Courier(Chicago)

Chicago, IL

$2,800 - $4,800

Grubhub

Early Morning Grubhub Driver

Chicago, IL

$2,200 - $3,800

Auto Logistics Pros

Independent Contractor Driver-Auto Parts Courier•Chicago,IL•Auto

Chicago, IL

$2,800 - $4,800

Shipt

Earn Extra Cash:Midday Shopper(Chicago)

Chicago, IL

$1,000 - $2,000

Final Mile Delivery Co.

Independent Contractor Driver-Final Mile Parcel(Gig Economy And

Chicago, IL

$3,000 - $5,500

Urban Pedal Logistics

Chicago Career:Independent Contractor Driver-Urban E-bike/scooter

Chicago, IL

$2,500 - $4,500

Last Mile Logistics Network

Independent Contractor Driver - Last-Mile Logistics

Chicago, IL

$2,940 - $5,250

Uber

Ubereats Delivery Driver Position in Chicago | Hiring

Chicago, IL

$2,500 - $4,500

Uber

Chicago Contractor Ubereats Large Order Delivery Driver | Hiring

Chicago, IL

$3,500 - $6,000

Auto Logistics Pros

Independent Contractor Driver - Auto Parts Courier

Chicago, IL

$2,576 - $4,416

Grubhub

Night Shift Grubhub Courier

Chicago, IL

$2,576 - $4,416

Regional Expedite Logistics

Independent Contractor Driver-Long Distance / Regional Courier(Gig

Chicago, IL

$3,500 - $6,000

Driving Jobs in Chicago — FAQ

How many driving jobs are available in Chicago, IL right now?
There are currently 140+ 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 140+ listings above and apply directly.

Last updated: April 26, 2026