I have been going to Second City for about 4 years now, pretty much every time they change up the main show. I have to say, I LOVE it. I have no issues with the shows. They indeed make me laugh hard. Now you are looking at spending just under 30 dollars for your tickets, however when you consider you are watching a show the price isn't too bad. Also the whole atmosphere is pretty cozy and intimate with the performers. These are generally skit com's which are well thought out and draw you into the different performers acting.
They have a pretty good menu which includes all sorts of alcohol and pub foods which are pretty tasty. The servers are very friendly and really work hard at keeping you happy.
While you are watching the show you can't help but feel the legacy which the place is. So many great Canadian comedians started here and they have there's cast member pics posted all the way though the theatre.
The one draw back I can think of is the seating. It's pretty tight as well as the tables generally being shared by your nabour making your side pretty small. I would say this makes for a great second or third date, but not a good first date.
I will keep going whenever new shows are brought out.