About the Role
Position Overview
Legacy Route Transport is seeking reliable and professional Independent Contractor Drivers to operate box trucks and cargo vans for local and regional deliveries. Contractors will handle general freight and time-sensitive deliveries throughout the Chicago area and routes up to 500 miles.
This is a 1099 independent contractor opportunity, offering flexible scheduling and the ability to accept or decline loads based on availability.
Key Responsibilities
Pick up and deliver general freight safely and on time
Complete local same-day deliveries and regional routes (up to 500 miles)
Load and unload cargo as required
Follow dispatch instructions, routes, and delivery time windows
Maintain communication with dispatch and customers
Ensure all deliveries are properly documented (photos, signatures, etc.)
Operate vehicle in a safe, professional manner at all times
Vehicle Requirements
Must own or lease a:
Cargo Van or
Box Truck (typically 12–16 ft, under 10,000 lbs GVWR)
Vehicle must be clean, reliable, and well-maintained
Recommended equipment:
Straps / tie-downs
Dolly or hand truck
Moving blankets
Driver Requirements
Must be 21 years or older
Valid driver’s license (CDL not required for qualifying vehicles)
Clean driving record (MVR required prior to approval)
Ability to lift 50–75 lbs
Strong time management and communication skills
Professional attitude and appearance
Insurance Requirements
Must carry commercial auto insurance
Proof of insurance is required before starting
Some drivers with exceptional driving records and coverage may be eligible to be added to company insurance (case-by-case basis)
Screening Requirements
All applicants must successfully complete:
Background check
Drug screening
Motor Vehicle Record (MVR) review
Work Schedule & Flexibility
On-demand and scheduled routes available
Flexible schedule — accept or decline loads
Must be available for occasional:
Early morning routes
Evening or weekend deliveries
Regional trips
Compensation
Paid per route, stop, mile, or load (based on contract)
Competitive rates based on vehicle type and delivery scope
Payment issued upon successful completion of contracted work
Important Notes
This is an independent contractor (1099) position, not employment
Contractors are responsible for:
Their own vehicle
Fuel, maintenance, and operating expenses
Consistent, reliable drivers may receive priority for higher-paying routes
Apply Today
Join Legacy Route Transport and become part of a growing logistics network focused on reliability, efficiency, and professionalism.
Requirements
Basic Eligibility Requirements
Must be 21 years or older
Valid U.S. driver ’s license (CDL typically not required for vehicles under 10,000 lbs GVWR)
Clean Motor Vehicle Record (MVR) (no major violations in last 3 years)
Must pass:
Background check
Drug screening
Must be legally authorized to work in the U.S.
Vehicle Requirements
Must own or lease a:
Cargo Van or
Box Truck (typically 12–16 ft, under 10,000 lbs GVWR)
Vehicle must be:
Reliable and well-maintained
Clean and presentable
Equipped with:
Straps / tie-downs
Dolly or hand truck (recommended)
Blankets or padding (for certain loads)
Must pass a basic vehicle inspection (visual + safety)
Insurance Requirements
Must carry commercial auto insurance including:
Liability (commonly $100K–$1M depending on contracts)
Cargo insurance (amount varies, often $50K–$100K)
Must provide proof of insurance
Some drivers with strong records may be eligible to be added to company insurance (optional case-by-case)
Work & Delivery Expectations
Deliver general freight (may include:
Medical supplies
Retail goods
Equipment
Palletized or loose cargo)
Handle:
Local routes (same-day Chicago area)
Regional routes (up to 500 miles from Chicago)
Ability to:
Lift 50–75 lbs (sometimes more depending on freight)
Load/unload cargo (unless dock-assisted)
Follow:
Delivery schedules and time windows
Route instructions and dispatch communication
Availability & Flexibility
Must be available for:
On-demand loads
Scheduled routes (daily/weekly)
Willing to:
Work early mornings, evenings, or weekends if needed
Take long-distance trips (same-day or overnight)
Technology Requirements
Smartphone required (iPhone or Android)
Must be able to use:
GPS/navigation apps
Dispatch/load apps
Photo/signature confirmation tools
Professional Standards
Strong communication with dispatch and customers
Professional appearance and attitude
Punctual and reliable
Ability to follow instructions and adapt to changes
Compliance & Documentation
Must provide:
Driver’s license
Insurance documents
Vehicle registration
Motor Vehicle Record (MVR)
Must comply with:
Local and state transportation laws (Illinois regulations)
Company safety policies
Independent Contractor Terms
This is a 1099 contractor position (not employee)
Drivers:
Use their own vehicle
Cover their own fuel, maintenance, and expenses
Can accept or decline loads
Paid per:
Route
Stop
Mile
or load (depending on your structure)
Rates are communicated and agreed upon before accepting each load or route.
Payment Terms
Contractors are paid after successful completion of deliveries
Payment is issued only after Legacy Route Transport receives payment from the client
Standard payment cycles may vary depending on client terms (e.g., Net 7, Net 15, Net 30)
Contractors must submit all required delivery documentation (POD, photos, signatures) to receive payment
Important Contractor Pay Notes
This is a 1099 independent contractor position (not hourly employment)
Contractors are responsible for:
Fuel
Vehicle maintenance
Insurance
Tolls and operating expenses
Contractors may accept or decline loads based on offered rates and availability
Higher-paying opportunities may be offered to contractors with:
Strong performance
Reliability
Clean driving record
Professional service
Earning Potential
Earnings vary based on availability, routes accepted, and efficiency. Contractors who consistently accept routes and perform reliably will have greater access to recurring and higher-paying opportunities.
About the Company
At Legacy Route Transport, we provide specialized transport solutions designed for the modern supply chain. By utilizing versatile equipment, we offer a unique advantage in navigating urban environments and meeting tight delivery windows that larger carriers often miss.
Our operations are built on a foundation of reliability and precision, specializing in the secure transport of general freight and non-hazardous medical logistics. We serve as a critical link for businesses requiring last-mile efficiency and professional handling of sensitive commercial and healthcare cargo.