Nowadays, 100MB is not enough for /boot. Do not bypass the problem: solve it. I would try to boot a live system, copy (with 'cp -a') the content of the /boot partition on the respective directory on the root partition. You can then delete the small /boot partition (e.g., using GParted) and extend the root partition (or any other adjacent partition) to not lose the freed space. Then you would have to remove the respective line in /etc/fstab. Finally, you need to 'chroot' (see https://help.ubuntu.com/community/Grub2/Installing#via_ChRoot) the root partition to then 'update-grub'.

Reinstalling is an option too...

And, of course, always backup your data.

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