About us
Founded in 2013 in Chicago, IL, Windy City has grown from a local carrier to a trusted partner with nationwide coverage across all 48 states. As a family-owned company, we combine asset-based capacity with modern technology to deliver reliable, scalable solutions for every load. With 300 company-owned trucks and 400 branded trailers, plus strategic yards in Chicago, Jacksonville, and Dallas, we ensure faster transit times and dependable support. Powered by MacroPoint, Samsara, and Geotab, we offer real-time tracking, 24/7 updates, and full shipment visibility. Our dedicated in-house dispatch team works around the clock, providing direct, seamless communication no middlemen, no excuses. From full truckload and dedicated lanes to drop trailer programs, we move freight efficiently and keep your business moving forward.
What makes us different?
Transforming Freight with Transparency, Speed, and Dedication
Strategic Yards
With key hubs in Chicago, Jacksonville, and Dallas, we ensure faster transit times, optimized routes, and dependable local support for your shipments.
Our Fleet
Operating 300 company-owned trucks and 400 branded trailers, our modern fleet is ready to deliver across all 48 states with consistency and reliability.
Our Assets
From fully branded, company-owned equipment to a strong network of lease-to-own and owner-operator partners, we have the capacity to meet your transportation needs.
Real Time Tracking
Powered by MacroPoint, Samsara, and Geotab, our advanced systems deliver 24/7 GPS tracking, ETA updates, and complete shipment visibility for total peace of mind.