Chicago · Chicagoland
Cook County · Served by Riskara Insurance Group
Chicago is the freight crossroads of the United States. Six Class I railroads converge here, three of the country's busiest interstates (I-90, I-94, I-55) pass through Cook County, and BNSF, UP, NS, and CSX run intermodal terminals across Chicagoland. We write commercial trucking insurance for Chicago-based owner-operators, drayage carriers, and small-to-mid fleets — from the intermodal lots in Bedford Park to the food-distribution warehouses on the South Side.
Yes. Drayage is one of the highest-frequency risk classes in the Chicago market — short hauls, dense intersections, plus heavy intermodal yard exposure. We have multiple carriers with active appetite for Chicago drayage on container, tank, and reefer.
Three things, in order: CDL violations within the last 36 months, a recent at-fault accident with bodily injury, and a CSA score above FMCSA intervention thresholds. If any of those apply to your fleet, we have non-standard markets that will still write you — at higher premium.
If your principal place of business is outside Illinois, the policy is written in your home state with Chicago-area garaging disclosed. Coverage is identical; only the rating territory changes. Tell us your domicile when you quote.
Owner-operator or 50-unit fleet — upload your USDOT info and loss runs and we'll come back fast.
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