Driving Jobs in Chicago, IL — Start This Week

As of May 2026, there are 240+ open driving positions in Chicago, IL. Current pay ranges from $500 to $10,000 per year. Top hiring areas include Delivery Driver, General and Cdl Driver. New roles are posted daily — listings on this page are verified and updated regularly.

Uber

Apply Now:Night Shift Rideshare Driver in Chicago | Hiring

Chicago, IL

$3,200 - $5,500

Uber

Chicago Career:Night Shift Driver at Uber | Hiring

Chicago, IL

$2,816 - $4,840

Shipt

Weekend Shift:Early Morning Shopper-Chicago

Chicago, IL

$2,200 - $3,800

Uber

Chicago Event Driver(Contractor)-Uber | Hiring

Chicago, IL

$3,080 - $5,500

United States Postal Service

Rural Carrier Associate (RCA)

Chicago, IL

$3,672 - $5,184

United States Postal Service

Neighborhood Postal Carrier

Chicago, IL

$3,960 - $6,050

Urban Pedal Logistics

Flexible Gig:Independent Contractor Driver-Urban E-bike/scooter

Chicago, IL

$2,700 - $4,860

Urban Pedal Logistics

Urgent Hire in Chicago:Courier

Chicago, IL

$2,500 - $4,500

National Grocery Delivery Network

Chicago Job:Driver Opportunity(No Exp Req*)

Chicago, IL

$2,500 - $4,500

Uber

Chicago-based Night Shift Rideshare Driver Opening | Hiring

Chicago, IL

$3,200 - $5,500

Uber

Chicago-based Rideshare Driver Opening | Hiring

Chicago, IL

$3,000 - $5,000

DoorDash

Bicycle/E-Bike DoorDash Courier (Urban Delivery)

Chicago, IL

$2,500 - $4,500

Driving Jobs in Chicago — FAQ

How many driving jobs are available in Chicago, IL right now?
There are currently 240+ 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 240+ listings above and apply directly.

Last updated: May 08, 2026