Oh yes, to add to this, Sunday Gospel Brunch at Dick’s Last Resort (near the Navy Pier) is worthwhile. I mean, Dick’s is a chain and I usually kick myself for going to chain in a city I’m visiting, but I fricking hate those stuffy hotel brunches on Sundays. For the same price you can get an amazing assortment of damn good food at Dick’s, in a much more casual (!!) atmosphere, and with a kick-ass gospel group pounding away for entertainment.
Hey, this is great. My wife and I are going to Chicago for a wedding this spring and we’re planning to spend a couple extra days looking around. Thanks for the suggestions everyone.
More jazz than blues again, but most Chicagoans I know are awfully fond of the Green Mill. Used to be an Al Capone hang-out, now it’s the oldest jazz venue in the US. It’s on Lawrence and Broadway, and is maybe a block from the Lawrence stop on the red line. The California Clipper is also a kick-ass bar, and has live music Thurs-Sun., with Fridays reserved for blues. It’s on California and Augusta, and has great vibe. Used to be a speakeasy, now it’s kind of a swank dive bar, if you can get into that. Not sure of the public trans route for that one, though.