Driving Jobs in Winona, MN — See Openings

As of May 2026, there are 40+ open driving positions in Winona, MN. Current pay ranges from $736 to $8,500 per year. Most openings are in Delivery Driver. New roles are posted daily — listings on this page are verified and updated regularly.

Urban Pedal Logistics

Winona Job:Independent Contractor Driver-Urban E-bike/scooter Courier

Winona, MN

$2,500 - $4,500

United Parcel Service (UPS)

UPS Package Delivery Driver Position in Winona | Hiring

Winona, MN

$4,000 - $7,500

National Grocery Delivery Network

Earn Extra Cash:Driver Opportunity(Winona)

Winona, MN

$2,375 - $4,275

Grubhub

Night Shift Grubhub Courier

Winona, MN

$2,548 - $4,368

Final Mile Delivery Co.

Winona Independent Contractor Driver-Final Mile Parcel with

Winona, MN

$3,000 - $5,500

Local Shopper Partners

(Winona)Part-Time:Courier

Winona, MN

$1,900 - $3,325

Secure Document Couriers

Independent Contractor Driver-Night Shift Legal/document Courier(Gig

Winona, MN

$2,800 - $5,000

Heavy Freight Logistics

Winona Independent Contractor Driver-Cargo Van / Box Truck Specialist

Winona, MN

$5,000 - $8,500

Wholesale Transit Partners

Winona Needs:Driver Opportunity(Part-Time)

Winona, MN

$3,360 - $5,775

Grubhub

Grubhub Delivery Driver

Winona, MN

$2,875 - $5,175

Midday Logistics Co.

(Winona)Part-Time:Driver Opportunity

Winona, MN

$1,000 - $2,000

Midnight Logistics

Urgent Hire in Winona:Late Night Convenience & Grocery Courier

Winona, MN

$2,800 - $4,800

Driving Jobs in Winona — FAQ

How many driving jobs are available in Winona, MN right now?
There are currently 40+ open driving positions in Winona, MN. 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 Winona?
Driving job pay in Winona 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 Winona?
Yes. Many delivery driver, courier, and DSP positions in Winona 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 Winona?
Driving jobs in Winona 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 Winona?
Benefits vary by employer, but many driving positions in Winona 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 Winona?
Your take-home pay as a driver in Winona 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 Winona?
Yes, many driving positions in Winona 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 40+ listings above and apply directly.

Last updated: May 04, 2026