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Health Insurance for 1099 Workers and Freelancers in Maryland: 2027 Guide
Quick answer: As a 1099 worker in Maryland, no employer picks a plan for you. You buy on Maryland Health Connection or choose a private PPO, and you may be able to deduct the premiums.
Why your income estimate matters
For the marketplace you estimate your yearly net income. Because 1099 income varies, an estimate that is too high or too low can mean repaying part of a subsidy or missing one. For 2027 the credit ends at 400% of the poverty level, about $63,840 for one person. Open enrollment for 2027 marketplace coverage began November 1, 2026. Most HealthCare.gov deadlines are December 15 for a January 1 start and January 15 for the final day, but state marketplaces set their own dates, so confirm yours on marylandhealthconnection.gov.
Marketplace or private?
If your net income is under the line, compare marketplace plans first. If it is above, or you want a national PPO, compare private plans on Cigna, Aetna and PHCS PPO. Maryland runs its own state-based marketplace, Maryland Health Connection, and limits short-term plans to three months with no renewals. Private options here are narrower than in most states, so the honest answer is usually a careful comparison, not a promise of savings.
Taxes
Self-employed 1099 workers can generally deduct premiums they pay, up to net profit, if they were not eligible for an employer plan. Set aside money for quarterly estimated taxes and talk to your CPA. Maryland has a progressive state income tax plus a county income tax, so the self-employed health premium deduction helps at the federal, state and local level.
Changing jobs and income
If your income changes mid-year, update your marketplace application so your credit matches. Private plans do not adjust to income.
See live private-plan pricing or check your options and we will run both markets for you. Prices, carriers and rules change, so treat anything here as a starting point, not a quote.