Yes. I purchase the annual policy from Amex. Trips can be purchased with miles, Visa, or whatever and you are still insured. I regularly combine multiple reward and revenue tickets. In Jan I did a 2 week trip to SIN/LGK which had 7 different tickets/PNRs. Everything worked fine on this particular trip, but the insurance saved me on a trip to BKI last year.

https://insurance.americanexpress.ca/travel-insurance/

Only works for mechanical or weather delays however.