Winners Transportation delivers end-to-end transportation services combined with expert consulting designed to strengthen your operations from the ground up.

We analyze your current operations, identify bottlenecks, and uncover hidden inefficiencies.

Based on our findings, we develop a custom optimization plan tailored to your business.

We implement solutions alongside your team, providing hands-on support until results are achieved.
01
Winners Transportation operates across all 48 contiguous states. We run OTR (Over-the-Road) long haul routes primarily out of our Oakbrook Terrace, Illinois headquarters, with strong lane coverage throughout the Midwest, Southeast, Southwest, and both coasts.
02
We provide full truckload service across three equipment types: dry van for general commodities and packaged goods, refrigerated (reefer) trailers for temperature-sensitive and perishable shipments, and flatbed for oversized, heavy, or irregularly shaped cargo. Each freight type is handled by drivers who specialize in that equipment.
03
Contact our team directly by calling +1 (708) 571-0464 or sending an email to info@winnerstrans.com. You can also fill out the form on our Contact page. We typically respond within one business day with rate and availability information.
04
Yes. Our entire fleet runs electronic logging devices (ELDs) that provide real-time location data. Your assigned dispatcher monitors every load and provides proactive check calls so you always know where your freight is without having to ask.
05
Yes, we're actively hiring both company drivers and onboarding owner operators. We offer competitive CPM pay, weekly direct deposit, late-model equipment, and flexible home time. Call our recruiting line at +1 (331) 336-4909 or visit our Contact page to apply.
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