I have my flights booked to fly to Canada on 17th February with just 15 more days left on my visa and study permit. Would I be allowed to re-enter and extend my stay in Canada? Is it safe to say I wont be deported?
Nothing related to obtaining a visa or granted entry is entirely safe. Unless you have other issues you haven't mentioned, have not already graduated, etc you will be allowed entry. Make sure you have all your documents in order to present at the airport if requested.
If you want to extend your stay in Canada as a student, you must apply before the expiry date on your study permit. Complete the Application to Change Conditions or Extend Your Stay in Canada. You should apply for renewal at least 30 days before your current permit expires.