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My Microsoft email address and account are linked to Skype, OneDrive and Windows 10 (products I use by Microsoft).
This account is not linked to my phone (Android).
I don't use this account for Email (I use Gmail for email).
Absolutely sure I don't have private data/conversations in OneDrive.

Today I have looked at my "Junk Email" on my Microsoft email account.
I have a number of spam emails about "tinnitus", "tired of that ringing in your ears", "the sound from inside your head".
And emails about "home security equipment", "loan", "keep your home safe", "never pay for covered home repairs".

I had conversations about these 2 subjects recently on Skype (in the past months).
I don't use Bing or Cortana to search about these subjects. I always use Google on Google Chrome to search.

This makes me very worried, as this makes it very suspicious that my Skype chats are being shared with 3rd party or similar.
I really can't think of another way these spammers would know that I have interest for "tinnitus".

Any ideas or explanations?

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When you search on Google or Bing you have an advertising identity associated with you. Any terms that you search for then become part of that profile. Your keywords of interest are then sold to third party advertisers who can then target you for future adverts. These advertisers then share the data between each other in data markets, each adding in whatever information they know about you in order to build a more rich profile. They want to know things like your age, your gender, marital status, what car you drive, what sports you're into, etc. so they can show you ads that you're more likely to click on. This is often called "tailored advertising" or "customised advertising".

Now, technically those advertisers shouldn't get your email address. My guess is they've correlated it from another advertising platform that didn't properly redact your identity. This is common practice for shady advertisers and there are hundreds of them out there, so it's hard to track.

If your concern is that advertisers are snooping on your Skype conversations, I'd say it's unlikely. That kind of advert metadata extraction is done on some platforms (e.g. Facebook messenger conversations on the web client) but as far as I know it isn't done on Skype.

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