Driving Jobs in Chicago, IL — Start This Week

As of April 2026, there are 230+ open driving positions in Chicago, IL. Current pay ranges from $440 to $10,000 per year. Top hiring areas include Delivery Driver, Cdl Driver and General. New roles are posted daily — listings on this page are verified and updated regularly.

Uber

Chicago Contractor WAV Driver | Hiring

Chicago, IL

$3,500 - $5,500

Secure Document Couriers

Independent Contractor Driver - Night Shift Legal/Document Courier

Chicago, IL

$2,800 - $5,000

United States Postal Service

Class A CDL Tractor Trailer Operator - USPS

Chicago, IL

$5,775 - $8,400

Uber

Weekend Driver•Chicago,IL•Uber | Hiring

Chicago, IL

$2,000 - $3,500

United States Postal Service

Assistant Rural Carrier (Weekend & Holiday Delivery)

Chicago, IL

$1,500 - $2,500

Uber

Night Shift Driver($3.6k-$6.2k/Month)-Chicago,IL | Hiring

Chicago, IL

$3,584 - $6,160

Uber

Work in Chicago:Rideshare Driver | Hiring

Chicago, IL

$3,000 - $5,000

Heavy Freight Logistics

Chicago Contractor Independent Contractor Driver-Cargo Van / Box Truck

Chicago, IL

$4,400 - $7,480

DoorDash

College Town DoorDash Driver

Chicago, IL

$2,600 - $4,800

Corporate Courier Logistics

Part-Time B2B Route Logistics Driver Job in Chicago | Part Time

Chicago, IL

$3,679 - $5,520

Final Mile Delivery Co.

Recruiting in Chicago:Final Mile Parcel | Hiring

Chicago, IL

$2,550 - $4,675

Urban Pedal Logistics

Independent Contractor Driver - Urban E-Bike/Scooter Courier

Chicago, IL

$2,700 - $4,860

Driving Jobs in Chicago — FAQ

How many driving jobs are available in Chicago, IL right now?
There are currently 230+ 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 230+ listings above and apply directly.

Last updated: April 17, 2026