Windy City Express Freight Inc.
Company Overview
Fleet Size
11
power units
Tractors
9
owned
Trailers
—
owned
Drivers
12
total
Address & Contact
20200 W Governor''S Drive Suite 101, Olympia Fields, IL 60461
Services & Equipment
Cargo Carried
Classification
authorized for hire
Business Type
N/A
HazMat
No
Registration Details
MCS-150 Date
July 16, 2025
Annual Mileage
221,839 mi (2024)
CDL Drivers
12
Ready to automate your dispatch?
Dispatch with AI helps carriers like Windy City Express Freight Inc. save 50% of admin time with AI-powered automation. Manage your 11 trucks from one dashboard.
14 days free · No credit card required
Why Windy should try Dispatch with AI
- ✓AI Load Agent — Extracts loads from emails with 97%+ accuracy
- ✓Auto Billing — Invoices, driver pay, and IFTA in one click
- ✓Safety Agent — Proactive compliance alerts for licenses & insurance
- ✓GPS Tracking — Samsara & Motive ELD integrations
- ✓QuickBooks Sync — Two-way sync for invoices & expenses
Plans from $49/mo · 60-day money-back guarantee
AI-Powered TMS for Windy City Express Freight Inc.
Windy City Express Freight Inc. is a motor carrier based in Olympia Fields, Illinois (USDOT# 3051072, MC-49851). With 11 power units and 12 drivers, managing dispatch, billing, and compliance can be time-consuming and error-prone with traditional TMS software.
Dispatch with AI is an AI-powered transportation management system built specifically for carriers like Windy City Express Freight Inc.. Our AI agents automate load extraction from emails, invoice generation, driver pay calculations, and compliance monitoring — so your team can focus on moving freight, not pushing paper.
Plans start at $49/month with a 14-day free trial and 60-day money-back guarantee. No contracts, no setup fees.