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I can think of no biblical example where a believer prayed to any created being, which would include angels because angels are created beings. Jesus only instructed his followers to pray to God in heaven.
We have the instance of Stephen who, full of the Holy Spirit, looked up to heaven and saw the glory of God, and Jesus standing at the right hand of God. Stephen declared:
Look, I see heaven open and the Son of Man standing at the right hand of God (Acts 7:56).
As he was being stoned to death by the hostile Jews, Stephen prayed:
Lord Jesus, receive my spirit. Then he fell on his knees and cried out, Lord, do not hold this sin against them (Acts 7:59-60).
Here we have Stephen praying to the risen, resurrected and glorified Son of God. Given that Jesus is part of the One Being of God, and given that he co-existed from eternity prior to the incarnation, then there is no problem with Stephen praying to Jesus. Indeed, Jesus told his disciples that it is proper to address Him in prayer:
Whatever you ask in my name, this I will do, that the Father may be glorified in the Son. If you ask me anything in my name, I will do it (John 14:13–14).
Christians pray to God in heaven through Christ Jesus. See Matthew 6:9-13 and Luke 11:2-4. Jesus and the Holy Spirit mediate between the believer and the Father, so it stands to reason that prayer to Jesus and the Spirit are also acceptable:
My little children, I am writing these things to you so that you may not sin. But if anyone does sin, we have an advocate with the Father, Jesus Christ the righteous. He is the propitiation for our sins... (1 John 2:1–2).
Likewise the Spirit helps us in our weakness. For we do not know what to pray for as we ought, but the Spirit himself intercedes for us with groanings too deep for words. (Romans 8:26).
All Christian believers, who have been born again and are adopted into God’s family, can “approach God’s throne of grace with confidence” (Hebrews 4:16) when they address their prayers and petitions to the Creator, through Christ Jesus.
There are 650 prayers in the Bible, none of which are made by believers to any created being in heaven: https://www.gospelpedlar.com/articles/Christian%20Life/Prayer.pdf