About Us
Connecting the World, One Shipment at a Time
With decades of experience in logistics, we deliver cargo securely and efficiently across the globe. Whether it’s a single parcel or bulk freight, our tailored logistics solutions ensure timely delivery and complete transparency.
Our Services
Real-time tracking & visibility
Macropoint
Macropoint
Samsara
Samsara
Geotab
Geotab
Transport Types
Diverse Fleet for Every Freight Need
DRY VAN
Dry van trailers are the most commonly used type of semi-truck trailer, ideal for transporting non-perishable goods. They offer full enclosure, protecting cargo from weather and theft, making them a reliable choice for a wide range of freight.
REEFER
Reefer trailers are refrigerated semi-truck trailers designed to transport perishable and temperature-sensitive goods. They maintain consistent climate control, ensuring product integrity during long hauls and in varying weather conditions.
FLAT BED
Flatbed trailers are ideal for hauling large, heavy, or irregularly shaped cargo that doesn’t fit inside enclosed trailers. Their open design allows for easy loading and unloading from all sides, making them perfect for construction materials, machinery, and more.
Drop Trailer Programs
Nationwide coverage
(48 contigous states)
Dedicated lanes or flexible on-demand capacity
24/7 in-house dispatch
Our Strategic Yards In:
CHICAGO, Illinois
From major trade hubs to remote regions, we deliver worldwide.
JACKSONVILLE, Florida
Trusted by leading brands across industries.
DALLAS, Texas
Our in-house brokers ensure smooth cross-border shipping with near-perfect accuracy.
Chicago
Jacksonville
Dallas
OUR CORE SERVICES
Full Truckload Transportation (FTL)
Asset-Based Capacity
Real-Time Tracking & Visibility
Dedicated Dispatch & Support
Strategic Yard Locations
Drop Trailer Programs
FAQ
Got Questions? We’ve Got Answers
What services does Windy City Transportation provide?
Windy City Transportation offers flexible lease-purchase programs for semi-trucks, giving drivers the opportunity to work toward ownership while on the road. Our services include non-forced dispatch, competitive compensation, and reliable weekly payments. We also provide access to a wide range of late-model trucks and trailers available for lease, purchase, or rental.
How can I track my shipment in real time?
We use industry-leading technology such as MacroPoint, Samsara, and Geotab to provide 24/7 GPS visibility, ETA notifications, and geofencing, ensuring full transparency and direct communication with your team.
What is the advantage of working directly with you?
We operate under a direct carrier model with no middlemen, reducing costs, streamlining communication, and minimizing dwell time — delivering greater efficiency and reliability.
What is your fleet size and where are your locations?
We own 300 trucks and 400 trailers, working with both lease-to-own drivers and owner-operators. Our strategic yards are located in Chicago, IL and Jacksonville, FL.. We provide real-time shipment tracking through our online portal. You’ll receive a tracking number once your shipment is dispatched, allowing you to monitor its status at every stage.
Do you offer nationwide coverage?
Yes. We provide reliable and consistent transportation services across all 48 contiguous U.S. states, with options for dedicated lanes and flexible capacity.