When I was last at Harlem, they told us that they have live music upstairs on Fridays and Saturdays. Sounds like it's sometimes jazz, but you'd want to check first, I imagine, to confirm who's playing.
there's a place in Roncesvalles with jazz and dinner. otherwise, look into who's playing at Hugh's Room and Lula Lounge. The food at Hugh's is OK and I was very impressed with the food at Lula's. Ten Feet tall has jazz on Sundays.
www.sopra.ca or www.therex.ca. Sopra is much more elegant and the food is of a different (read: higher) calibre, but if you don't mind a bit of grit the Rex is a fun spot for more budget-conscious night.