Sentry Insurance: Truck Insurance in Illinois (2026)

Sentry Insurance is a leading commercial truck insurance carrier in Illinois. SafeBridge Insurance has direct relationships with Sentry Insurance and compares quotes from 15+ carriers to find the best rate.

Sentry Insurance Strengths

Largest dedicated DSP book, fleet operations

Average Premiums in Illinois

  • Local: $9,500–$13,200/year per truck
  • Regional: $12,800–$17,500/year per truck
  • OTR: $14,200–$19,800/year per truck

Illinois Unique Factors

  • Chicago O'Hare/Midway — air freight hub
  • Chicago rail yards — intermodal trucking
  • I-55, I-80, I-90 — major Midwest corridors
  • Illinois Tollway — E-ZPass commercial fleet accounts

Also Compare With

Progressive CommercialGreat West CasualtyCountry FinancialCanal Insurance

Get Sentry Insurance Quote in Illinois

Free Quote(315) 871-0833

Full State Guide

Illinois Truck Insurance →
Taxes, regulations, FMCSA, best carriers