Through my first few playthroughs I played through chapter one almost the exact same way and I always assumed that there was no way to get the chalice, but on a playthrough from a little while ago, I had just started it because I wanted to borrow some of the different magic types for the april fools D&D campaign I've started hosting yearly, I played through it differently, and I think it might be possible to get it, I've been doing cheesed/save-scummed runs to see what all I can get from people, and my current theory is that Kane has it, but I'm not even sure how I'd manage to interact with him right now considering how I started this run, I'll update when/if I get the chalice

this one's absolutely spoilers kekw

Okay, so I ignored the kid at the start, convinced the one lady to tell me and aeran about the grey woman I forgot the actual name of, and then she took me to rayne, who told me some more stuff about what could've happened to fisher, then I went to relics and runes, taking over and interrupting aeran while intimidating the shop owner, then I grabbed some stuff from the shops and I'm now at where you put what you've found together with Aeran, and now there's on option to go to marshwall to investigate further, so I genuinely think there's a chance here

Edit: there's also what I assume is an option to go to the viridian lady, so you may actually also be able to get the chalice to hera too

Edit 2: Im playing somebody with Aeda ancestry trained by sero just incase that has an Impact

This ones more spoilers, do not read further if you haven't reached marshwall and made it to chapter 2 from there yourself and want to discover that on your own

Right so the member of the seven in marshwall got killed via a messy hit, then you can gaslight rhodarth into thinking you have the chalice, although it's ineffective. Then you get taken back to the count, theres also a cube in the seven member's home

theres a whole host of new options with the count, one of them has to be the orb from Hera, but another is the cube, and two to three of them are just lying about who has the chalice, the other two choices are telling him what you found in marshwall and blaming the count himself.

telling him what you found in marshwall just gets you basilisked
giving him the cube makes him kill rhodarth, rhodarth then brings himself back, the count takes the cube, stating that it must be attuned to the user before it has an effect, thanks you and then takes you into the villa

the first of two lying options I can access is to tell the count that Lars Drakehand, the owner of relics and runs has the chalice, if succeeded, the count doesn't belive you anyway and you get basilisked

the second of the two lying options I can access is to tell the count that the Saffron Duchess aka marshwall member of the seven, has the chalice, if succeeded, the count believes you, but still basilisks you anyway

blaming the count obviously gets you basilisked

so the only real new option here is to give him the cube, and go into the villa with him, where the count requests your "permanent service" in exchange for your continued life

from here we get new options, those being to forge a pact with him and stay under his service, refuse his offer, or lie and accept his offer, then get out

refusing his offer sets you into a fight, a new one, not the basilisk, winning the fight just ends you up with a cleaner good basilisk ending

forging a pact with the count lets you ask him to let aeran go, which will send you into the same fight as above, or ask him to let aeran stay with you, but the count cannot lay a finger on him, to which the count ignores and sends you into the same fight as above.

lying to the count and passing the persuasion check lets you go into the same dialogue tree as forging the pact. but now you can attempt to persuade him into letting you and aeran have a final night, which is ineffective and sends you into the same fight

I know I can get new results, I just have to try again.

Still spoilers 

went to the viridian lady this time instead of the runes and relics place, which revealed that the third option after combining info was not her place, but floatsam grove, I'll see if going to marshwall yields new results first though.

going to marshwall gave me nothing new, sadly

I WAS PLAYING THROUGH THE GROVE BEFORE WRITING A NEW ENTRY AND ITS HERE!
IT'S IN THE HANDS OF AN ENEMY BUT IT'S HERE

Thank you so much, Deadpotatos! I'm glad you found the chalice. It is a genuine joy to read your account of figuring out where it could be.