I'm not sure if you can sing, but they often have professionals doing the honors at Uncommon Ground. This is one of Chicago's best coffee houses. and the menu is pretty good. It does close a little early though.
1214 West Grace Street
Chicago, IL 60613
Another spot, a bit off the beaten track is the open mike every Saturday night at
Some Like It Black
Open Mike - Every Saturday at 8pm
4500 S. Michigan, Chicago, IL
Some Like it Black is a coffee shop on the southside inside of a historic Chicago Mansion. Open only occasionally (I think perhaps only on Saturday, though they used to open other nights of the week as well) it is a mostly young crowd from the neighborhood.
Some of the most incrediable performances I've seen at an open mike in Chicago, many accompanied by music. Truly a unique and interesting night out - especially if you bring a piece to read yourself (most people will be reciting from memory, but they don't mind if you need to read off paper).
Exactly the sort of small, community place I think more people from all over Chicago should make it out to.
(been a while since I was there, but yes, I did read a few pieces when I was there)
Well not sure about the "sing" part, but a few places come to mind:
- Fireside Bowl - open 24hrs, not sure about the eats there but an option
- 3rd Coast Cafe - doubt you can sing, but definitely under 21 friend (cafe bar) but serves for those over 21. Good food, open late.
- Pick Me Up Cafe - in Wrigleville, 24hrs at least on the weekends, large under 21 crowd.
There may be some Korean Kareoke places that are open to an under 21 crowd as they are restaurants, not "just" bars. Could be a very good option for eccentric, but fun places - look around Lincoln & Lawrennce for a number of them, search this board for Orange and for the Korean threads for addresses & other details - definitely a part of Chicago that warrents further exploration.
hope this helps - if I think of any others I'll post again.