Deduct insurance premiums

Yes, if you pay your healthcare insurance out of pocket (not deducted from wages or pension), you can claim that as part of medical expenses. It becomes part of your total itemized deductions, so depending on what else you can deduct, it may or may not reduce your taxes. 

1. Use the search box toward the upper right corner to search for Medical expenses. 
2. Next, click on Jump to medical expenses.
3. The first question will say, Did you spend more than $XXXX on medical expenses in 2019?
4. The figure quoted there is 7.5% of your AGI. That amount will be deducted from your total out of pocket medical expenses. 
5. If you think you have enough to make a difference, go ahead and add the information about your expenses.

There are other deductions that can be taken in this section too, such dental and optical insurance, eye exams, hearing aids, prescriptions, co-pays, etc.

You only get a benefit from itemizing if your total of itemized deductions is more than your standard deduction for your filing status.