Whether itemizing will work out for you is hard to say.  We do not know your filing status, or what itemized deductions you can enter.  In late January, you will receive a 1099R for the distribution from the retirement account., Go to  Federal> Wages and Income>Retirement Plans and Social Security>IRA  401 k) Pension Plan Withdrawals to enter your 1099R.

Your itemized deductions have to be more than your standard deduction before you will see a change in your tax owed or tax refund.  The deductions you enter do not necessarily count “dollar for dollar;” many of them are subject to meeting  tough thresholds—medical expenses, job-related expenses, casualty and theft losses, for example, must meet thresholds that are pretty hard to reach.  The software program uses all the IRS rules that apply to the expenses you enter, and it tells you if you have enough to use your itemized deductions or if using the standard deduction is more advantageous for you. Here are the Standard Deductions for 2017

Your standard deduction lowers your taxable income.  It is not a refund 

2017 Standard Deductions

Single    $6350  (65 or older + $1550)

Married Filing Separately   $6350  (65 or older +  $1250)

Married Filing Jointly           $12,700  (65 or older + $1250@)

Head of Household $9350  (65 or older + $1550)