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Health Insurance for Small Business Owners in Illinois: Solo to 20 Employees
The right answer changes with headcount. Here's the path for Illinois business owners.
Just you (and family)
You're an individual buyer. Subsidy-eligible after deductions → Get Covered Illinois. Above the line and healthy → private shared-network PPO on Cigna, Aetna and PHCS PPO. Deduct premiums above the line. Illinois has a flat 4.95% state income tax, so the self-employed premium deduction helps at both levels.
Two lives — you plus one
A spouse on payroll, a partner, or one W-2 employee opens the small-group market, which is guaranteed-issue with employer-style networks. For two healthy people it's often close to two private plans; for two people where one has a condition, it's frequently the best answer.
3–20 employees
Level-funded and traditional small-group plans. Employer contribution is tax-deductible to the business, and offering coverage is a hiring advantage in Chicago's labor market. Under 50 employees there's no mandate to offer it — it's a choice.
Mixed 1099 and W-2 teams
Common in Illinois: a couple of W-2 staff and a bench of 1099 contractors. The W-2s go on a group plan; the contractors each buy individually, and we can set them all up through the same office so nobody falls through.
Illinois moved to its own state-run marketplace, Get Covered Illinois, for 2026 coverage, and Chicago-area marketplace plans are heavily HMO — one reason suburban business owners look at national PPOs.
Check your options — tell us your headcount and we'll map the path.