I cancelled my Illustrator subscription and now wish to renew instead.

that's interesting.  people complain that they're unable to schedule plan cancellation.  

when did you cancel?

and to answer your question, set a reminder to restart your subscription the day before it ends.  or just contact adobe support and see if they can seemlessly do what you want.

there are 3 ways to contact adobe; chat, phone and twitter:

chat:
use a browser that allows popups and cookies
and click here, https://helpx.adobe.com/contact.html?rghtup=autoOpen
in the chat field (lower right), type AGENT
be patient, it can take quite a while to reach a human.

phone:
https://helpx.adobe.com/contact/phone.html

twitter:
tweet @AdobeCare

p.s. if you're contacted by anyone (via email or private message), it's much more likely to be a scammer than an adobe representative. ie, double check for an employee badge if contacted in the forums and look for an adobe.com domain in the email address if you click reply to an email. then check again and be very suspicious. any other method of contacting (or offering to contact you) is almost certainly a scam, https://community.adobe.com/t5/using-the-community-discussions/staying-safe-in-the-adobe-support-community/td-p/12919684/redirect_from_archived_page/true