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Weekend Driving Jobs in Milwaukee, WI (NOW HIRING)

Kept Companies

Weekend Pressure Washer Technician

Milwaukee, WI · On-site

$16.50 - $21/hr

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

Valid Driver's License with a clean driving record * Must be 21 years of age or older * Experience ... Must be able to work weekdays Monday - Friday 6am to finish- Some weekends are required Benefits

ABM

Weekend Cleaner

Milwaukee, WI · On-site

$13.75 - $16.25/hr

Driving possibility, together. ABM is an Equal Employment Opportunity (EEO) employer that does not discriminate on the basis of any trait or characteristic protected by applicable federal, state, or ...

Hearst

Weekend Anchor Reporter

Milwaukee, WI · On-site

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

... weekends and carry up to 50 pounds ... Have a valid driver's license and a clear driving record * Have and exhibit unwavering journalistic ...

ABM

Weekend Cleaner

Milwaukee, WI · On-site

$13.75 - $16.25/hr

Driving possibility, together. ABM is an Equal Employment Opportunity (EEO) employer that does not discriminate on the basis of any trait or characteristic protected by applicable federal, state, or ...

PVH

Sales Associate - Part-Time- Weekend Availability

Kenosha, WI · On-site

$13.75 - $18.50/hr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

S.: the people, organizations and ideas boldly driving the future of Fashion, Art, Music ... Flexible schedule including nights, weekends and holiday availability * Competitive pay * Brand ...

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All JobsDriving JobsWeekend Driving JobsWeekend Driving Jobs in Milwaukee, WI

Weekend Driving information

See Milwaukee, WI salary details

$16

$25

$37

How much do weekend driving jobs pay per hour?

As of Aug 13, 2026, the average hourly pay for weekend driving in Milwaukee, WI is $25.80, according to ZipRecruiter salary data. Most workers in this role earn between $20.87 and $29.62 per hour, depending on experience, location, and employer.

What skills and qualifications are needed for weekend driving?

To thrive as a Weekend Driver, you typically need a valid driver's license, a clean driving record, and thorough knowledge of local traffic laws and routes. Familiarity with GPS navigation systems, ride-sharing or delivery apps, and basic vehicle maintenance are commonly required. Strong customer service skills, punctuality, and the ability to remain calm under pressure help drivers stand out. These skills ensure safe, efficient, and reliable transportation or delivery services, which are critical for customer satisfaction and professional success.

What is weekend driving?

Weekend driving jobs are positions that involve transporting passengers or goods primarily during the weekends, often on a part-time or flexible basis. These roles include driving for ride-share services, delivery companies, or transporting goods for local businesses. Weekend driving jobs are ideal for people looking to earn extra income outside of their regular weekday commitments. Drivers typically need a valid driver's license, a clean driving record, and sometimes their own vehicle, depending on the employer.

What are the typical work schedules and expectations for weekend driving?

Weekend driving roles often require flexibility, as shifts may start early in the morning or extend late into the evening, depending on demand. Drivers may be expected to handle higher passenger or delivery volumes during peak hours, such as Friday and Saturday nights. Communication with dispatchers or customers is key, and drivers should be prepared for variable traffic conditions. Regular vehicle checks and adherence to safety protocols are also important parts of the job. Team interaction varies, but drivers typically coordinate closely with support staff to ensure smooth operations.

What is the difference between Weekend Driving vs Weekend Delivery Driver?

AspectWeekend DrivingWeekend Delivery Driver
CredentialsDriver's license, clean driving recordDriver's license, vehicle insurance
Work EnvironmentPersonal vehicle, roads, highwaysDelivery vans/trucks, client locations
Industry UsageTransportation, logistics, personal commutingFood, retail, e-commerce deliveries
Common Search IntentDriving jobs on weekends, personal drivingWeekend delivery jobs, courier work

Weekend Driving typically involves personal or professional driving on weekends, often for commuting or transportation services. Weekend Delivery Drivers focus on delivering goods or packages during weekends, usually for retail or food services. While both roles require a valid driver's license, the main difference lies in the work environment and job purpose. Understanding these distinctions helps job seekers find roles that match their skills and schedule preferences.

What are the most commonly searched types of Driving jobs in Milwaukee, WI? The most popular types of Driving jobs in Milwaukee, WI are:
What cities near Milwaukee, WI are hiring for Weekend Driving jobs? Cities near Milwaukee, WI with the most Weekend Driving job openings:
Weekend Driving jobs near you
Infographic showing various Weekend Driving job openings in Milwaukee, WI as of August 2026, with employment types broken down into 76% Full Time, 22% Part Time, and 2% Contract. Highlights an 89% Physical, 1% Hybrid, and 10% Remote job distribution, with an average salary of $53,670 per year, or $25.8 per hour.

Instructional Trainer-Truck Driving

Waukesha County Technical College

Pewaukee, WI • On-site

$29.17 - $31.50/hr

Full-time, Part-time

Medical, Dental, Life, Retirement, PTO

Re-posted yesterday

Job description

Salary: $29.17 - $31.50 Hourly
Location : WCTC Pewaukee Campus, 800 Main Street, Pewaukee, WI 53072, WI
Job Type: Part Time (21-29 hours/week)
Job Number: 2025-07-16TW
Department: Graphics, Construction, & Transportation
Opening Date: 09/30/2025
Grade/Level: SA7
Description
This position is responsible for driving and related operational skills training for students in the Truck Driving program. This position does not have responsibility for the course, but instead works in open labs to support student learning.
Characteristic Duties and Responsibilities (include, but not limited to)
ESSENTIAL DUTIES AND RESPONSIBILITIES:
  1. Demonstrate and supervise student driving in lab under a variety of environments and driving conditions, including, but not limited to, straight line backing, developing depth perception, making turns, backing into docks and parking places, mirror adjustment, and how to use large mirrors and convex mirrors.
  2. Provide training for students in the truck driving program and students seeking a CDL. This includes administering driving simulations and brake board activities, demonstrating shifting techniques, coupling/uncoupling of semi-trailer combinations, performing vehicle inspection, providing collision avoidance training, and completing scaling activities.
  3. Administer CDL exams
  4. Ensure truck driving equipment is functional and safe. Perform light maintenance on and washing/cleaning of vehicles. Maintain lines on driver training areas. May act as liaison between truck driving program and repair shop. Coordinate purchase of supplies as needed.
  5. Provide assistance in training new instructional assistants
  6. Assist in truck dispatch and use of facility/resources
  7. May assist with program recruitment efforts, such as semi-annual Open Houses events
  8. Other duties as assigned

Minimum Qualifications
REQUIRED KNOWLEDGE, SKILLS, AND ABILITIES:
  • Ability to drive all truck and trailer combinations offered in the truck driving program
  • Ability to plan, organize, and facilitate quality training
  • Ability to work effectively with students, both in one-on-one and group instruction situations
  • Ability to think critically by applying problem solving practices
  • Effective interpersonal communication skills - oral, written, technical and non-technical information, and listening
  • Strong customer service skills, working with individuals from diverse backgrounds
  • Ability to establish and maintain positive working relationships with colleagues
  • Ability to work independently, as part of a team and/or with minimal supervision
  • Basic level of proficiency with computer software applications such as word processing, spreadsheets, databases, presentations and/or publishing.
EDUCATIONAL AND EXPERIENCE REQUIREMENTS:
  • Must possess and maintain a valid Class A Commercial Driver's License (CDL) with air brake endorsement
  • Three years' experience operating large trucks and 48' or 53' trailer required. Seven years strongly preferred.
  • Training and teaching experience in the truck driving industry preferred
  • Experience with van, flatbed, tanker, and doubles preferred
  • In evaluating candidates for this position, the College may consider a combination of education, training, and experience which provides the necessary knowledge, skills, and abilities to perform the duties of the position
  • Employment offer and continued employment is contingent upon negative DOT drug test(s) and acceptable driving record
  • Certified examiner preferred

Supplemental Information
This position supports the Graphics, Construction, and Transportation department and will report to the Associate Dean of Graphics, Construction, and Transportation.
This position requires Wisconsin residence.
This position is part-time, as needed, working up to 24 hrs/week.
The final candidate will have to pass a driving test.
Application detailsAll applicants must submit a completed application along with the following attachments:
1. Current resume (required)
2. A cover letter (optional)
3. Copy of current CDL licensure
Interviews
A final interview date is to be determined.
**Position will be posted until filled**
WCTC provides excellent benefits for our employees. Typical benefits for full-time employees (part-time employee benefits may be prorated) may include:
  • Medical/Dental Insurance
  • Term Life Insurance *
  • Disability Insurance *
  • 403(b) Tax Sheltered Annuity
  • Deferred Compensation
  • Vacation
  • Sick Leave
  • Personal Days
  • Holidays
  • Flexible Spending Accounts
  • Wisconsin Retirement System (if schedule to work at least 1,200 hours per year)
  • Tuition Reimbursement (full-time only)
  • Employee Assistance Program
  • Wellness Activities

* Not available to limited term employees.

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