When you turn 65, you need to either sign up for Medicare, or have a qualifying medical insurance that covers you through work or where ever. When you get past the enrolment time frame, the possibility exists that you may need to medically qualify for Medicare, if you don't have existing qualifying medical coverage at whatever point your existing coverage no longer covers you. For instance, my wife is older then I am, she was covered by a very good insurance at her place of employment, that also covered me (at additional cost) until I reached 65. Even after she retired from that place, as long as she paid the retirement coverage on herself, they would continue to cover me at the same rate as before. When I turned 65, that policy ended, and we both had to sign up for Medicare. Because she was covered by an approved insurance plan, delaying the signup for Medicare wasn't a problem for her, but she did have to provide proof of that insurance coverage to Medicare when she turned 65. Had she not had the approved insurance, and had waited to sign up for Medicare, she may have had to qualify for Medicare like you would for starting most any other insurance policy, with medical questions. When you sign up for Medicare at 65, there are no medical questions, everyone is covered.

The time frame from converting from "privet" insurance and Medicare is within 30 days of your 65th birthday. You open one, and close the other, it is one of the more precise government operations out there. You really need to look into your options 60 to 90 days before you turn 65, so your decision can be made by your birthdate.

Most company insurance offers other options for the company insurance policy once you get past 65, they may or may not be a good deal.

Medicare part A (major medical basic coverage, you pay the first 20% up to a limit) is pretty much required, and they take from your SS check $468 (I think without looking) each month. That number is adjusted nearly every year.
Medicare part B (a supplement designed to pick up most of that 20%, +ER coverage and has a few extra perks) is an option you pay extra for, also deducted from your SS check.
Medicare part D (this would be prescription drugs and such) is another option deducted from your SS check.

In IL there are basically 3 companies that have IL approved " Advantage Supplemental Insurance Plan" options you can choose rather then Medicare, during the "enrolment period time frame" that rolls around every year. Its likely your state is set up the same way. You can join any of them when you turn 65, but then have to re-signup when the next enrolment time comes around. I turned 65 in September, I had to enroll in a Medicare approved policy, then when the enrolment period came around in Dec, I had to signup again, and all the deductibles started again.

Those 3 insurance companies are the only options other then Medicare in IL. Everyone trying to get you to enrollee is pushing one or more of those companies, and each of their prices vary widely. I think the current company choices is Aetna, Humana, or Blue Cross/Blue Shield. Each of those companies have a couple of options, every option has advantages and disadvantages, or you can choose to stay with Medicare (with or without the supplement, or prescription coverage). Next year you can choose again during the enrolment time, but starting with one of the insurance companies then going back to Medicare introduces the medical questions. Choose wisely.

If you choose one of the insurance policies, the government will deduct the monthly premium from your SS check and send it to the insurance co.