High-paying loads for experienced drivers
boss transport INC Drive with us
Join a reliable trucking company based in Chicago. We specialize in oversized loads and provide consistent work, strong support, and competitive pay.
about us
Boss Transport INC is a Chicago-based trucking company specializing in open-deck and oversized freight.
We work with experienced drivers and owner-operators who are looking for steady loads, reliable dispatch support, and competitive pay.
Our focus includes flatbed, step deck, RGN, and extendable trailers for freight that requires skill, attention, and the right equipment.
why drivers choose us
- High-paying loads
- Consistent work
- Flexible schedule
- Dispatch support
- Fast payments
- Professional team
our specialization
We specialize in the type of freight that requires skill — and pays more.
Oversized loads
Extendable Flatbed
Adjustable length for oversized loads (48–80 ft / 53–90 ft).
General freight
Flatbed
Standard open trailer for general freight (construction materials, machinery, pallets).
Heavy equipment
rgn
Designed for heavy equipment (drive-on loading for machinery).
Tall loads
step deck
Lower deck for taller loads (no height limits like dry vans).
real work in action
how it works
01
Apply online
02
Our team contacts you
03
Get approved
04
Start driving & earning
become a driver
Fill out the form below and our team will contact you within 24 hours
frequently asked questions
Do you work with owner-operators?
Yes, we work with both company drivers and owner-operators. We provide competitive rates and steady work for all qualified drivers.
What type of loads do you offer?
We specialize in oversized cargo, heavy equipment, construction materials, and machinery. Our loads are consistent and high-paying.
How often do drivers get paid?
We offer fast payment schedules with weekly pay options. Our goal is to ensure you receive your earnings promptly and reliably.
Do you provide dispatch services?
Yes, we provide full dispatch support. Our professional team handles load coordination so you can focus on driving and earning.
become a driver
Fill out the form below and our team will contact you within 24 hours