Driving Jobs in Winona, MN — Hiring Now

As of April 2026, there are 30+ 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)Part-Time:Courier

Winona, MN

$2,500 - $4,500

National Grocery Delivery Network

Earn Extra Cash:Driver Opportunity(Winona)

Winona, MN

$2,375 - $4,275

Grubhub

Part-Time Grubhub Driver (Lunch Rush)

Winona, MN

$736 - $1,656

Grubhub

Suburban Route Grubhub Driver

Winona, MN

$2,400 - $4,200

Wholesale Transit Partners

Winona Needs:Driver Opportunity(Part-Time)

Winona, MN

$3,360 - $5,775

Local Merchant Delivery Network

Work in Winona:Independent Contractor Driver-Early Morning

Winona, MN

$2,400 - $4,200

Morning Express Couriers

Winona Needs:Driver Opportunity(Part-Time)

Winona, MN

$2,310 - $3,990

FreshDrop Logistics

Flexible Hours:Driver Opportunity-Winona

Winona, MN

$3,150 - $5,775

Auto Logistics Pros

Auto Logistics Pros seeks Independent Contractor Driver-Auto Parts

Winona, MN

$2,800 - $4,800

Corporate Catering Couriers

Apply Today in Winona:Independent Contractor Driver-Catering Logistics

Winona, MN

$3,500 - $6,000

Midday Logistics Co.

(Winona)Part-Time:Driver Opportunity

Winona, MN

$1,000 - $2,000

Grubhub

Grubhub Delivery Driver

Winona, MN

$2,875 - $5,175

Driving Jobs in Winona — FAQ

How many driving jobs are available in Winona, MN right now?
There are currently 30+ 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 30+ listings above and apply directly.

Last updated: April 26, 2026