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I think like a grid,so therefore I am a grid.
I would take Western straight down,and then swing a right on Addison and go straight to Ravenswood....
however, let's talk reality here ,my good cycle brethren....you live right by the Orange line.Take that into the loop,and then bike it up to
Addison via Clark or hit the bike trail on the lake front .
I love to cycle great distances myself, but to endure a commute like that everyday?..... no way.......maybe once a week.....but not eveyday......balance it out some.
Here's what I would do*:
Find a painless way to 47th (sidewalk? Western is a death trap for bicycles at your latitude, whether you take the Ave. or the Blvd). 47th to Racine. Racine north to Hayes and Loomis. Loomis to Blue Island to Racine, west on Hubbard all the way to Damen, then Damen to Roscoe to Ravenswood to your destination.
...
I would consider Halsted from 47th to 63rd to be "ride at your own risk" unless you've got ride partners. It's fine through Bridgeport and Pilsen. From Harrison to Division, you've got very frequent stop lights (timed to make you stop OFTEN) and very bad pavement in some places.
From 51st, California is a better ride - moderate traffic, mostly residential. I've ridden it from 71st to Howard, and I like most of it. California to Division to Damen could give you a decent ride.
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