Fromper |
As Berti mentioned, there's Pathfinder Society play at the Dice Dojo every Monday evening. It's near the red line stop at Broadway and Bryn Mawr, so should be easy for you to reach. Check out www.cowsgaming.org for details.
Fromper |
Nope. Just show up.
It's best to sign up in advance on the COWS web site, so they know how many players to expect and how many GMs they need. It's also good to bring a character, but if you don't know how to make one, or aren't comfortable with Pathfinder Society rules, you can just show up and play a pregenerated character for your first session. You'll get lots of advice on how to make a character when you're there.
There are other groups around the area, too, but most are in the suburbs. So if CTA's your only transportation, they aren't as convenient.
For instance, now that I've moved to the northwest suburbs, I don't play at the Dojo any more, but I've started playing at Games Plus in Mt. Prospect every Sunday. Here's a link to that group's signup page. There's also a group that meets in Downer's Grove on Sundays.