You could start by looking at the
Blues Listings in the Reader.
Although their music is more of a Jazz/Blues fusion, than traditional Chicago Blues, I would be tempted to go see Erwin Helfer and Skinny Williams at Katerina's tonight. I have never seen them perform together, but both are excellent musicians. Erwin is one of the the preeminent Chicago blues pianists, who has worked over the years with many of the old-school Chicago blues legends, as well as giving many younger artists their start in the business. Skinny Williams is an accomplished saxaphonist, who has toured with numerous jazz, funk and blues artists. Together, I am sure they are remarkable.
I have never been to Katerina's either. It is a fairly new club/cafe/bistro offering "Southern European" cuisine.
Their menu looks pretty interesting, featuring mostly sort of nouveau-greek small dishes and a few entrees. Maybe someone else has been there and can give a quick review.
Katerina's
1920 W. Irving Park
773-348-7592.
UPDATE: I happened to re-check Katerina's website to see what time the music started tonight, and discovered that Erwin and Skinny were no longer listed as appearing tonight. Oh Well. It WOULD have been good. Melvin Taylor is at Rosa's. He can be fun. Rosa's is kind of a dive, but it has an "authentic" blues club vibe. There are some good Mexican Restaurants in the vicinity like Fonda Del Mar at Fullerton and Hamlin.
Rosa's Lounge
3420 W. Armitage
773-342-0452