Lightning fees tend to be about 0.5% at the higher end; on-chain fees are currently about $1, though it does vary day to day. So LN is cheaper if you are sending <$200 at a time. There's lots of goods and services that cost less than that.

Also, lightning is a superior experience in many ways. Settlement is a matter of seconds, not minutes. And privacy is significantly better than on-chain in most cases. So personally I always prefer LN even if it's more expensive.

I've done lots of ~$1000 LN transactions with my own self sovereign node, both sending and receiving. You do need channel capacity to well connected nodes for thet to work. But if you do it works fairly well.