Chicago · Chicagoland

Commercial auto insurance in Chicago, IL

Cook County · Served by Riskara Insurance Group

Chicago's commercial-auto market is enormous and diverse — from contractor pickups working downtown buildouts to last-mile delivery fleets serving Cook County, from livery and limo operations to the trucking industry that makes Chicago the freight crossroads of the country. We write all of it.

Why Chicago is different

  • Contractor commercial auto for downtown Chicago buildouts, the L-extension work, and Cook County infrastructure projects.
  • Last-mile and final-mile delivery fleet coverage across Chicagoland.
  • Limo and livery commercial auto for licensed Chicago operators.
  • ICC intrastate authority filings for Illinois-only commercial fleets.
  • Carriers with active Chicago appetite: Progressive Commercial, Northland, Cover Whale, Nirvana.

Coverages we write

  • Primary liability ($750K – $2M+)
  • Motor truck cargo
  • Physical damage (tractor, trailer, equipment)
  • Non-trucking liability / bobtail
  • Hired and non-owned auto
  • General liability
  • Trailer interchange
  • Excess / umbrella liability
  • Workers' compensation (referrals)
  • Occupational accident

Chicago Commercial Auto FAQs

Do you write commercial auto for contractor crews working downtown Chicago?

Yes. Pickups, vans, dump trucks, and crew trucks for contractors are one of our largest commercial-auto classes. Most contractor commercial fleets are written through Progressive Commercial or similar standard markets at substantially lower rates than trucking-only programs.

Can you write Chicago-licensed limo and livery operations?

Yes. Limousine and livery is a regulated, separate appetite from standard commercial auto. We have markets that write Chicago-licensed transportation operators including livery, limo, and shuttle services.

What's the minimum primary liability for commercial auto in Chicago?

Standard commercial auto in Illinois starts at the state minimum (25/50/20). For commercial purposes, most carriers require $300,000 combined single limit minimum, and contracts (shippers, GCs, municipalities) frequently require $1,000,000 or $2,000,000.

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