Bedtime regression or anxiety or something else..

Hi everyone I'm new and wondered if someone was going through this similar thing, my son who's now 6 when he was on summer break from school, seemed to develop anxiety, he didn't want to go to sleep or eat then he went back to school and he was fine, progressed with writing reading everything, now we're in lockdown, and we've actually been in it for 5 weeks now, and 4 nights ago, crying out for me, whimpering, banging on the Windows,until I come and see him, last night was the worst, took 3 hours to go to sleep, that's not all, he was sick with chest infection for 2 weeks in lockdown and needed medicine, now it seems the only way he will go down is if he has medicine, I try to placebo it but he knows the difference, like I said in the header, I'm wondering if it's a mix of all these or I made a crack abny now who cos he knows he can't go to school because of cough as we call it, thinks I must be unwell so I need medicine, but when go to see him at night, he instantly stops crying and smiles, it feels like where getting played, he is only just learning about feelings and understanding, his language is emerging but not great, I called the doctor, but I got that in a week, this lockdown could could go on for months.. Can someone help.