The Blues are about to embark on a sprint finish to the end of the season, playing eight games in 27 days starting with Birmingham City at home on Easter Monday.
League leaders Coventry City look to be away and clear, nine points above second-placed Middlesbrough.
But Boro, Town, Millwall and Hull City are all in the hunt for the second automatic promotion place.
And former Premier League star Waddle, who now works for Radio Five Live, thinks Town will emerge from that scrap.
Kieran McKennaKieran McKenna's Town are in the race for automatic promotion (Image: Ross Halls)
He told Fruity King: "This year has been the best year to ever get out of the Championship. This has been the year where a lot of teams people would never have mentioned are knocking on the door like Millwall, Middlesbrough and Hull City.
"Ipswich Town are a team we all thought would be up there but nobody thought it’s very difficult to know who else will make it because I think Ipswich will take second with the experience they have and the size of their squad."
He added: "Middlesbrough just can’t seem to get over the line. They looked certain to be second earlier in the season. Now they’re getting beat 1-0 at home. They can’t score goals.
"I'd go for Ipswich to finish second now because of the experience and in the playoffs, I think you normally get a team who comes into it in form, going on a run, and you’d have to look at Southampton for that. I wouldn't want to go and play there at the moment."
But regardless of who goes up this term, Waddle believes all three will come straight back down - just as they did when Town were last in the Premier League.
He opined: "The Championship is such an ordinary league this year that, for me, it's the easiest the Championship has ever been.
"If Ipswich go up this year would they have the money to do what Sunderland did and spend £300 million? No, I don’t think so.
"Whoever goes up, that’s the goal, to win promotion. It’s another goal entirely to stay in the league.
"Burnley struggled. Sunderland did well because they spent a fortune. Leeds have struggled because they didn’t spend like Sunderland did, and Leeds were the best team in the Championship last season with Burnley.
"Burnley hardly conceded a goal in the Championship and look what happens to them in the Premier League. It's a completely different competition.
"Looking at all the clubs that could go up, I would say the three that will go up will be the three who come back down next season."
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