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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:

1. Click on Federal Taxes
2. Click on Deductions and Credits
3. Under All Tax breaks, locate the section Medical and click on Show more
4. Click Start next to Medical Expenses.