My first reaction to you riding across the west side on Madison was: Don't Do It.
I picture a cyclist being knocked over and robbed, or worse.
I pulled out my Chicagoland Bicycle Federation (CBF) map to see what they recommend as a bike route. They say Washington is a better street for biking than Madison, as it has marked bike lanes. In my opinion, there's no good way to get across the west side, especially at that latitude. It's not the Skid Row it used to be, but it's still a very rough neighborhood, especially between Austin and Western. You might want to drive Washington and compare it to Madison in terms of the bike lane. Do cars respect that lane? Can you get away fast if you need to? You might even want to go to a CBF www.biketraffic.org or Chicago Cycling Club http://www.chicagocyclingclub.org/ meeting and ask what they think.
I've lived in Chicago for 28 years. I ride my bike all over. I have yet to find a good route across the west side. My sister lives in Oak Park, and one of my goals for this summer is to find a decent way to ride out there. I am farther north than you (I start from Addison and Western). I have less fear of being mugged than I would if I were riding in the Garfield/Douglas/Humbolt Park area, but all E/W roads are very traffic heavy, and therefore uncomfortable and dangerous. The expressway cuts across all routes--you have to be on a road that goes under it, or you end up riding way out of your way to stay on smaller streets. I'll figure it out.
Good luck--I think the idea of commuting is a great one, and hate that we're talking about the risk of being attacked en route.L.




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L.
