You can claim all medical bills and health insurance premiums (including Obamacare) paid out-of-pocket as Medical Expenses in Schedule A - Itemized Deductions
Medical Expenses are subject to the 10% rule (or 7.5% if you are over 65) and you can only claim the excess over 10% (or 7.5%) of your Adjusted Gross Income.
Please note that Itemized Deductions will only "help" when they total more than your standard deduction.
For 2016, standard deductions are:
For a taxpayer under 65, not claimed as a dependent
- $6,300 for Single
- $12,600 for Married Filing Jointly, or Qualifying Widow(er) with dependent child
- $9,300 for Head of Household
- $6,300 for Married Filing Separately
- If you are over 65 or blind, add $1,250 for each instance or add $1,550 each instance if single and not a surviving spouse
In TurboTax, you can enter Medical expenses by following these steps:
- Click on Federal Taxes
- Click on Deductions and Credits
- Under All Tax breaks, locate the section Medical and click on Show more
- Click Start next to Medical Expenses.
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