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From Return of the Jedi (emphasis mine):

A lonely, windswept road meanders through the desolate Tatooine terrain. We HEAR a familiar BEEPING and a distinctive reply before catching sight of ARTOO-DETOO and SEE-THREEPIO, making their way along the road toward the ominous palace of Jabba the Hutt.

THREEPIO: Of course I'm worried. And you should be, too. Lando Calrissian and poor Chewbacca never returned from this awful place.

We know that Lando disguised himself as a guard. Chewbacca, however, didn't come to Jabba's palace until later, when Leia brought him. There's nothing to indicate he was there earlier, and if he was, it would be odd that Jabba didn't mention this when he was later brought to him.

Is there some deleted scene or EU work that explains the apparent discrepancy?

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    At the end of ESB Chewie and Lando are heading out on the MF to rescue Han. I've always assume they've been on or around Tatooine since then, scoping out the joint. Lando appears to have infiltrated the palace. Meanwhile Chewie has stayed outside, and connected with Leia for their part of the rescue plan.
    – zipquincy
    Commented Dec 14, 2015 at 15:20
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    Speculation: it's likely they didn't tell 3PO the plan. He certainly didn't know they were to be gifts to Jabaa. Considering R2 has Luke's lightsaber and seems to be in on the whole thing - 3PO, who is more likely to blab the details if pushed or afraid, was left in the dark. He probably thought the three of them were just going to go blast in and return with Han.
    – NKCampbell
    Commented Dec 14, 2015 at 15:27
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    3PO definitely didn't know - recall he said "gifts? what gifts!?" when R2 offered themselves to Jabba. He was shocked and terrified.
    – NKCampbell
    Commented Dec 14, 2015 at 15:34
  • @MikeEdenfield - R2-D2 was in on the whole plan. C-3PO was kept in the dark and just told that he was there to deliver a message.
    – Valorum
    Commented Dec 14, 2015 at 15:59

2 Answers 2

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According to the film's Junior Novelisation, C-3PO has been deliberately deceived by Leia and told that Chewie was taken by a bounty hunter.

In the event that he's tortured or sliced (or simply blabs their plans because he's a putz) it won't blow their scheme:

The awful place was their destination: Jabba the Hutt’s palace, a large fortress near the southwestern border of the Western Dune Sea. But as the droids trudged once again across the desert world’s desolate terrain, R2-D2 was more optimistic about the fate of their friends. For one thing, Lando could take care of himself pretty well. Also, the droid knew that Chewbacca hadn’t even arrived yet at Jabba’s palace, although he didn’t bother mentioning this detail to C-3PO. Sometimes, the less C-3PO knew, the better. The astromech droid rotated his domed head to whistle a timid response to his gold-plated companion.

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The most obvious explanation is that C-3PO wasn't trying to imply that the two had arrived together, he was mentioning two people who had gone to rescue Han and not come back. The biggest problem with his statement, really, is that he fails to mention Leia at all; presumably he knows that she also failed to come back, but doesn't seem to worried.

Another, likely explanation is that Lando and Chewie did go to Tatooine together, initially, to rescue Han. I don't think we ever get the entire "plan" laid out for us, but it's likely that Lando was supposed to infiltrate Jabba's palace guard and leave an opening for Chewie to get in, defrost Han, and get out. For whatever reason, that plan failed, and Chewie was stuck on Tatooine. When Luke's plan B also failed, Leia decided to go in herself. (This may also have been pre-arranged, e.g. "if you don't hear from Chewie in 2 weeks, go to plan B. If that fails, go to plan C, etc.") When she got to Tatooine, she found Chewie waiting there and roped him into her plans.

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