How do i file both 1095-A and 1099-HC form for health insurance?

 Here’s how to enter 1095-A Health Insurance Marketplace Statement in TurboTax:

1. Select the search bar in the top right of your screen.
2. Search for Health Insurance and Select Jump to Health Insurance
3. When asked, Did you have health insurance coverage in 2017?, select either the first or second option, depending on your 2017 situation, and Continue.
4. When asked, Was anyone enrolled in a plan from a Marketplace?, select Yes.
5. When asked, What type of plan were you enrolled in?, select Obamacare plan (1095-A), and then Continue.
6. Follow the prompts to enter your 1095-A.
   1099HC
   In your Massachusetts return, you will reach the page Let's Go Over Your Health Insurance Information. As you continue, you'll reach a page "Let's Go Over Your Health Insurance Information". This is where you enter the information from your 1099-HC.

can I deduct the money I had to pay from 1095-A

Form 1095 provides information about your cost of health care coverage.  You will use the information from the Form 1095-A to calculate the amount of your premium tax credit. You will also use this form to reconcile advance payments of the premium tax credit made on your behalf with the premium tax credit you are claiming on your tax return.

If you enter your Form 1095A, you do not have to enter the premiums you paid out of pocket into the Medical Expense section of TurboTax. Instead just enter your 1095-A into the Health Care section and TurboTax will automatically apply the correct medical insurance premiums to line 1 of Schedule A, Itemized Deductions.