I doubt they could have escaped without Lando's help, but here are some speculations...
1. Luke arrives from Dagobah and Lando is looking the other way. Luke is fighting Vader and R2 splits off and joins with Leia, Chewie, and C-3PO. R2 hacks the computers and technobabbles his way through something that creates a distraction - just long enough for Chewie to smash some stormtrooper heads together and let them all escape.
2. In your scenario where Luke and R2 are still on Dagobah, Leia and Chewie are less likely to escape. It's still possible that Chewie would make the decision to f--- up the guards. He'd likely be shot in the process, possibly/probably fatally, but Leia might have escaped under those circumstances. Of course, without Vader being distracted by Luke and without R2 repairing the Falcon's hyperdrive, Leia and busted-up 3PO flying the Falcon to safety is...well, only Goldenrod could tell us the odds.
3. Chewie takes Han's admonition to protect Leia seriously and keeps his cool. They would be loaded on to Vader's vessel and it's unlikely they'd escape, at least initially. Leia obviously can't just pick locks or hack her way out of cells or she would have done so on the Death Star in Episode IV. Chewie probably couldn't break his way out, either, or he'd have busted his way out of the locked room in Cloud City. Since it's a Star Wars adventure film, though, I'd guess that they'd be on their way to the ol' torture chamber one day and they'd take advantage of a slip-up to mount a daring escape and bust out of there.
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