Health Insurance in Chicago, Illinois
Chicago runs on people who work for themselves: traders and tech consultants in the Loop, chefs and bar owners in Logan Square, rideshare drivers, actors, and the tradespeople rehabbing two-flats across the South and West Sides. Licensed in Illinois and working from Tampa, Frank Caballero helps Cook County families sort through their choices on a phone call or by video, in English or, if they prefer, Spanish. Illinois now runs its own exchange, Get Covered Illinois, which changes where many Chicagoans renew.
Chicago at a glance
- Where Chicago buys Marketplace plans: Get Covered Illinois, Illinois's own exchange
- Open enrollment for 2027 coverage: Set by Get Covered Illinois
- Illinois 2027 average rate change: 14% to 14.1% (finalized)
- Private plans: Any month, if approved
Who I help in Chicago
Trading and finance contractors, software and data consultants, chefs and bar owners, actors, improv performers and musicians, rideshare and delivery drivers, contractors rehabbing two-flats, truck owner-operators, nail and hair salon owners, and immigrant families running storefront businesses.
What to watch when choosing a plan here
Many Chicago individual plans are HMOs that cover only emergencies outside their service area. That matters if your family sees doctors in Northwest Indiana or southern Wisconsin, or if you live in the city and your specialist practices in a collar county. Six insurers filed for 2027, but some sell only in parts of Illinois, so a Cook County lineup can differ from DuPage, Will or Lake County.
Private plans and the Marketplace
Chicago households buy Marketplace plans through Get Covered Illinois. For 2027 the subsidy stops at 400% of the federal poverty level, $63,840 for one person and $132,000 for a family of four, and above that line every plan is full price. More on Illinois's numbers is on the Illinois 2027 premium increase page.
A private, medically underwritten plan is priced on age, ZIP code and health instead of income. You answer health questions, approval depends on them, benefits vary by plan, and private plans are not ACA Marketplace plans. If approved, one can start the first of any month, so it does not wait for open enrollment.
Areas served
Evanston · Oak Park · Naperville · Schaumburg · Skokie · Oak Lawn · Lincoln Park · Logan Square, all by phone or video in English or Spanish.
Compare Chicago plans
Private plans priced first, the Marketplace alongside when it fits. Phone or video, English or Spanish, no fee.
Chicago questions
Where do Chicago residents renew Marketplace coverage for 2027?
Through Get Covered Illinois, the exchange Illinois launched to replace HealthCare.gov for the 2026 plan year; it publishes its own enrollment calendar. This is only its second open enrollment, so returning enrollees should confirm that household and earnings details carried over correctly.
How much are Illinois rates going up?
Illinois finalized an average individual-market increase of about 14 percent, close to the national average; small-group plans jump about 17.6 percent. Chicago small employers facing that renewal can compare it with individual coverage for the owner and staff, and Frank can price both.
Can I stay on my group plan after a Chicago job ends?
Illinois law makes insured group plans give departing members up to a year of continuation after three months of being covered, and some divorced or widowed spouses can stay on longer. Weigh what continuation costs with a Get Covered Illinois plan or an underwritten private plan before deciding.
More for Illinois
Frank Caballero, licensed health insurance broker in Illinois and 30 other states, NPN 21032307. Based in Tampa, serving Chicago by phone or video. FC Insurance Solutions is independent and not affiliated with any government agency. Esta página en español.