I've been doing some thinking and some sleuthing, and I think I've come to logical conclusion (feel free to tell me I'm just tinfoil-hat-crazy, too).
Okay, so reports on Saturday were that Ohtani was in San Francisco to meet with the Giants. Monday, it appears as though Ohtani was in Florida with the Jays. But then you have Sunday...kind of a big blank day, no? Perhaps Ohtani took in some NFL football, a beer, and hanging out with friends, but I have a feeling that didn't happen. As well, there was the report that teams were coming to LA to meet with Ohtani for final meetings, but considering he went to SF and Toronto after (if reports are correct) it seems weird that would be the case, So maybe...what if it wasn't all teams on Saturday making their final pitch/meetings/tours of facilities but the two LA teams (one of which was a team he didn't need to tour, because, he's been an Angel for half a decade). Geographically, if Ohtani were making his tour around the other clubs, it would make sense that he would go from LA to SF, and this feels like it could be accomplished in a single day, like...Saturday. But again...Sunday....It'd make a lot of sense if Ohtani did something Sunday. And, again, thinking logically, planning a trip, geographically around the nation, well Chicago just so happens to be between San Francisco and Florida, and would have made quite the logical stopping place for a visit, wouldn't it have? And conspicuously, Jed Hoyer wasn't in Nashville Sunday. Neither was Craig Counsell. It really wouldn't make a ton of sense if they're both still in LA (Sunday and Monday) if they were meeting with him on Saturday. We know he's not in LA any more; he was in Florida Monday.
What I'm trying to get at is this: I think Shohei Ohtani was in Chicago Sunday. And I think the Cubs got him in and out without any leaks. Considering the Cubs were capable of doing this with Seiya Suzuki and Craig Counsell, it would track based on history. I could be way off, and fair, I'm going off logic/guessing. Both his trips to Toronto and San Francisco ended up getting reported/leaked in some way or fashion. If he got in and out of Chicago with zero leaks, I wonder how this helps on the final choice. If Ohtani is truly worrisome of leaks and quietness, which, if he' visiting teams in their cities during the Winter Meetings, you could argue is another reason to believe that, then the Cubs making this happen could help.
Edit: I'd also like to point out, the Cubs may have met in Arizona (someone else suggested this to me elsewhere, credit to him). Closer to the West Coast, easier to keep quiet. But regardless, I think very much so that the Cubs had their sit down with Ohtani on Sunday.