The actual words say “He descended into Hell; on the third day He rose again from the dead”.
It doesn’t say he spent the whole time He was dead in Hell, and indeed He did not.
Before Jesus died, nobody who had died previously, ever, could go to Heaven. Good people were sent to a place which we call “Hell” but which wasn’t the same as the “Hell” where sinners go with fire and everything. I believe the original word for the “Hell” to which all the dead went before Jesus was “Sheol” and it was basically a place where good people were comfortable but they could not be in the presence of God. So all these souls were down there waiting for Jesus to be born and live out his human life and die for all of our sins.
When Jesus died, he, and presumably the Good Thief who also died, went down to Sheol. At that point, Jesus opened up the gates of Heaven for all the good souls who had been sitting around in Sheol, and they all went to Heaven with Jesus. Jesus did this ASAP after He died; also remember that after death, you’re on God’s time, which is not the same as our human time. So this likely could have happened in a really short span of human time the minute Jesus died, because certainly Jesus, being God, was going to Heaven and he would not have been letting the good souls in Sheol wait a long time especially since his own earthly father St. Joseph was one of the deceased good souls waiting around down there.
So Jesus was correct in his words to the Good Thief, they all went to Paradise right after death, after Jesus made a quick visit to Sheol.
Jesus probably spent the rest of his time being “dead” up in Paradise and then returned to earth for the Resurrection.
Here’s the Catechism section on this.
http://www.vatican.va/archive/ccc_css/archive/catechism/p122a5p1.htm