I work two jobs. Can I have two health insurance plans from each employer?

I don’t see why you couldn’t purchase a health insurance policy from each employee if you’re offered a plan by each, but why would you want to pay for redundant coverage?

One plan won’t cover the other’s deductibles or co-payments, so I believe it’s better to research both plans and find out which fits your financial and medical needs and choose just that one. 

Having two policies could also be a nightmare for the coordination of benefits.  It’s possible that each health insurance provider might say that the other plan is primary.  Just for the potential red tape alone I wouldn’t recommend having health insurance plans with both employers.