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Yes, you can claim all medical bills and health insurance premiums 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 & Credits
• Under All Tax breaks, locate the section Medical and click on Show more
• Click Start next to Medical Expenses.