Driving Jobs in Milwaukee, WI — Start This Week - Page 5
180+ driving jobs in Milwaukee, WI hiring now — CDL, delivery driver, courier & more. $18–$90K+, many with benefits. See what's open in Milwaukee.
Secure Document Couriers
Independent Contractor Driver-Night Shift Legal/document
Milwaukee, WI
$2,800 - $5,000
Heavy Freight Logistics
Milwaukee:Independent Contractor Driver-Cargo Van / Box Truck
Milwaukee, WI
$5,400 - $9,180
Shipt
$40.50/hr Driver Opportunity-Milwaukee(PT)
Milwaukee, WI
$2,500 - $4,500
Sysco Corporation
Flexible Sysco Local CDL-A Delivery Truck Driver(Milwaukee)
Milwaukee, WI
$6,000 - $9,000
United Parcel Service (UPS)
Milwaukee Job:UPS Package Delivery Driver(Full-time) | Hiring
Milwaukee, WI
$4,000 - $7,500
Lyft
Lyft Needs Airport Transfer Driver in Milwaukee | Hiring
Milwaukee, WI
$3,500 - $5,500
Grubhub
Part-Time Weekend Delivery Professional – Milwaukee(Now Hiring)
Milwaukee, WI
$2,200 - $3,800
Uber
Uber(Milwaukee)Hiring:Event Driver | Apply Now
Milwaukee, WI
$3,219 - $5,750
Instacart
Dedicated Instacart Shopper & Driver
Milwaukee, WI
$3,449 - $6,324
United States Postal Service
Class A CDL Tractor Trailer Operator - USPS
Milwaukee, WI
$6,324 - $9,200
Local Merchant Delivery Network
Independent Contractor Driver - Early Morning Bakery/Floral
Milwaukee, WI
$2,400 - $4,200
Secure Document Couriers
Independent Contractor Driver - Night Shift Legal/Document Courier
Milwaukee, WI
$2,576 - $4,600
Last updated: May 04, 2026