Driving Jobs in Wauwatosa, WI — Now Hiring

As of May 2026, there are 50+ open driving positions in Wauwatosa, WI. Current pay ranges from $14 to $140,400 per year. Top hiring areas include Delivery Driver, Cdl Driver and Yard Jockey. New roles are posted daily — listings on this page are verified and updated regularly.

First Student

Wauwatosa School Bus Driver-CDL B With Passenger And S Endorsements

Wauwatosa, WI

$18 - $25

Urban Pedal Logistics

Wauwatosa Job:Independent Contractor Driver-Urban E-bike/scooter

Wauwatosa, WI

$2,500 - $4,500

Penske Logistics

Apply Now:CDL A Yard Hostler Truck Driver-Trailer Spotter in Wauwatosa

Wauwatosa, WI

$25 - $32

Hot Shot Transportation Co.

Hot Shot Transportation Co. Needs Hot Shot Truck Driver-Owner Operator

Wauwatosa, WI

$91,800 - $140,400

Uber Eats

$3.4k-$5.8k/Month Alcohol Delivery Driver job in Wauwatosa | Hiring

Wauwatosa, WI

$3,449 - $5,750

Regional Expedite Logistics

Independent Contractor Driver-Long Distance / Regional Courier

Wauwatosa, WI

$3,500 - $6,000

XPO Logistics

Wauwatosa Full-time Delivery Driver-Package Handler Box Truck

Wauwatosa, WI

$22 - $28

Instacart

Recruiting in Wauwatosa:Delivery Driver-Grocery Same Day Service

Wauwatosa, WI

$16 - $23

Wayfair

Delivery Driver-Furniture And Appliance Home

Wauwatosa, WI

$21 - $27

Instacart

Pet Supply Delivery Driver•Wauwatosa,WI•Instacart | Hiring

Wauwatosa, WI

$3,248 - $5,376

Matheson Postal Services

Wauwatosa USPS Mail Haul Truck Driver-CDL A

Wauwatosa, WI

$59,500 - $76,500

FedEx Custom Critical

$75k-$135k/Year Expedited Sprinter Van Driver-Time Critical Cargo job

Wauwatosa, WI

$75,000 - $135,000

Driving Jobs in Wauwatosa — FAQ

How many driving jobs are available in Wauwatosa, WI right now?
There are currently 50+ open driving positions in Wauwatosa, WI. 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 Wauwatosa?
Driving job pay in Wauwatosa 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 Wauwatosa?
Yes. Many delivery driver, courier, and DSP positions in Wauwatosa 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 Wauwatosa?
Driving jobs in Wauwatosa 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 Wauwatosa?
Benefits vary by employer, but many driving positions in Wauwatosa 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 Wauwatosa?
Your take-home pay as a driver in Wauwatosa 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 Wauwatosa?
Yes, many driving positions in Wauwatosa 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 50+ listings above and apply directly.

Last updated: May 14, 2026